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Villas in Berkshires

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    Travellers to Berkshires are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    All 158 Rentals in Berkshires
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    Berkshires: Romantic Cottage with spectacular view1 / 18
    (24)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Gartner House, a charming home in Lenox1 / 21
    (30)Excellent
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Stone School Cottage1 / 10
    (17)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Unique People & Pet-Welcoming Country Haven1 / 37
    (174)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Internet Access
    • Outdoor Dining Area
    • Air Conditioning
    • Shared Garden
    • Cable/satellite TV
    • Washer
    • Secure Parking
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 October 2018
    What a lovely cottage we found as we drove up a country road in Charlemont.And what a great,spotless and unusual country "suite" awaited us.A very large and beautifully...
    Reviewed 19 August 2018
    A cute cottage off the beaten trackDefinitely in the country but close enough to lovely cities. The scones and juice every morning were a treat.. the kitchen came in...
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    About this property
    Discover Cavalier Cottage B&B, a pet-friendly home away from your home and an attractive alternative to conventional hotels, motels and B&B’s. We warmly welcome visitors who come to this beautiful area of Western Massachusetts with or without their companion animals. Now in its sixth year,...
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    Charlemont, Berkshires 01339
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Berkshires Waterfront Lakehouse Sanctuary1 / 31
    (5)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • DVD Player
    • Hot Tub
    • Mountain Views
    • Waterfront
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    We thoroughly enjoyed our escape from nyc to the lake house. It was everything we hoped for: peaceful and secluded with gorgeous views of the lake. The house was fully...
    Reviewed 15 October 2018
    We were extremely grateful to have an opportunity to vacation with our black lab and were pleasantly surprised with not only the attractive amenities of the home, but the...
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    About this property
    Beautiful private peninsula like setting surrounded by a cove , stream and lake adorn this location. Waterfowl and birds are everywhere in this quiet spot just a few minute walk from the 11 mile Ashuwilticook Rail Trail. The house has undergone a total renovation and all the furnishings are new...
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    Lanesboro, Berkshires 01224
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    RiverSong Suite In The Berkshires1 / 52
    (14)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Patio
    • Air Conditioning
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 August 2018
    We eagerly anticipated our stay at RiverSong. Based on the plethora of five-star reviews we expected near-perfection. While we loved the atmosphere, fabulous comfortable bed...
    Reviewed 3 November 2017
    Riversong suite was wonderful, situated in a great location. Close to nearby restaurants and shops yet far from all the noise. Peaceful and quiet. A great place to renew...
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    About this property
    Located in the Berkshire mountains on more than 5 acres surrounded by 29 acres of conservation land. Featuring beautiful views of meadows, mountains and farm land bordering the crystal clear Green River (great trout fishing).Only 10 minutes from Great Barrington's Main Street stores, resturaunts,...
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    North Egremont, Berkshires 01230
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Waterfront Cottage - 10 Mins to Great Barrington!1 / 24
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Central Heating
    • Skiing: Property Is In A Ski Resort
    • Mountain Views
    • Waterfront
    • Patio
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 June 2018
    We had an excellent time with our two kids (7 and 8). The house is right on the lake with a great deck and amazing views. We used the kayaks every day. Location was great...
    Reviewed 22 June 2018
    Perfect location, perfect weather, beautiful view! Excellent owner, Carol, who responded to all our questions immediately. Would go back again in a minute.
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    About this property
    Let this serene lakefront Great Barrington area cottage in New Marlborough serve as your ultimate home-away-from-home! Featuring 2 bedrooms, 1-bathroom, and enough room to sleep 4 guests, this year-round vacation rental cottage is sure to give you an experience in the Berkshires that you will never...
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    New Marlborough, Berkshires 01230
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Plan your holidays in the Berkshires. Forecasting plenty of snow and mild temps.1 / 18
    (7)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Mountain Views
    • Wi-Fi
    • Balcony
    • Patio
    • Grill
    • Washer
    • Porch
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 September 2018
    The house was so comfortable; the location was perfect -- close to so many beautiful places and Berkshires attractions, especially Tanglewood!; Cassandra was so helpful when I...
    Reviewed 27 August 2016
    We had a wonderful stay in this large, lovely house that contained everything we needed for comfort and convenience. We were impressed with the degree to which details were...
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    About this property
    Located in West Stockbridge minutes from everything . Nestled in the Berkshire Mountains. Convenient yet Private. The Berkshires is a world unto itself. It is scenic beauty married to cultural bounty. It is urban sophistication in an idyllic, rural setting. It is a destination, a haven, a state...
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    West Stockbridge, Berkshires 01266
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Great Vacation House in the Berkshires on Richmond Pond1 / 10
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
    • Grill
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 August 2018
    Being Tanglewood lovers, this was the perfect vacation spot to enjoy the area's concerts, plays, art galleries and restaurants as well as the lovely Richmond Pond and the...
    Reviewed 28 August 2017
    This comfortable, breezy house was perfect! We loved being able to walk to the lake and canoe, play frisbee on the lawn, walk in the woods, eat on the deck, and gaze at the...
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    About this property
    Beautiful two bedroom house sits just steps from Richmond Pond. Enjoy a day on the water swimming and fishing followed by an evening enjoying the symphony at Tanglewood (ten scenic minutes away). Yoga enthusiasts will love the proximity to Kripalu (again, ten minutes away). Leaf peepers and skiers...
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    Richmond, Berkshires 01254
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Lakefront Berkshires Ski/Summer House, Great Views1 / 17
    (4)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Mountain Views
    • Grill
    • DVD Player
    • Waterfront
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 November 2017
    The house was cozy. The lake was beautiful. The surrounding towns offer great restaurants. The host was very helpful.
    Reviewed 16 November 2017
    We rented this lovely home on the lake (or maybe it's a pond... Long Pond I think) last year and loved every minute of our visit. The house is well equipped and has all one...
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    About this property
    Located in a wooded area overlooking a pristine lake, this woodsy style contemporary is a sportsman's paradise. It's a short drive to skiing (Jiminy Peak, Butternut, Catamount) and cultural attractions, (Tanglewood, National Music Center, Aston Magna, etc.) or you can fish, swim, boat, hike, or...
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    Great Barrington, Berkshires 01236
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Cozy & Modern Home -mins from Tanglewood & Kripalu1 / 8
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 December 2013
    We stayed at this home in Housatonic, which is part of Great Barrington, the Smithsonian pic for best small town in the USA. I hope you all don't however as one of the best...
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    About this property
    Cozy and modern two bedroom and one bath vacation home with lake nearby Come visit our brand new fully furnished cozy and modern vacation home in the Berkshires. This luxury home can sleep up to 6 people and has lake access nearby. Enjoy a nice cup of hot chocolate by the fireplace in the living...
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    West Stockbridge, Berkshires 01266
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come visit our brand new fully furnished cozy and modern vacation home in the Berkshires. This luxury home can sleep up to 6 people and has lake access nearby. Enjoy a nice cup of hot chocolate by the fireplace in the living room, fall foliage and scenic atmosphere in the area, and soak in the...
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    West Stockbridge, Berkshires 01266
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Mountain Views
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our nearly new home we call RiverSong is on 5.5 acres surrounded by almost 30 more conservation land of meadow and farmland. The pristine Green River is right in our back yard with a wonderful swimming hole. Our Penthouse room is on the upper level of our home. A Bright and spacious king size...
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    North Egremont, Berkshires 01230
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Comfortable Farmhouse in the Berkshires1 / 10
    (4)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Grill
    • Air Conditioning
    • Patio
    • Wi-Fi
    • DVD Player
    • Mountain Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 August 2017
    Nice house, great spot for our family reunion. Convenient to many of the Berkshires attractions. Nice kitchen for cooking and eating in for a group.
    Reviewed 6 June 2017
    House was comfortable and well furnished. The Berkshires are beautiful with lots of activities, galleries, shopping and restaurants. Our hosts were helpful and responsive to...
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    About this property
    Rent a comfortable 1840 farmhouse with 26 acres in the Berkshire mountains. Walk to the village of West Stockbridge or a short drive to all the Berkshire attractions. Close to the ski resorts of Butternut, Bousquet, Catamount and Jiminy Peak. The house sleeps 10 to 12 people and is fully equipped....
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    West Stockbridge, Berkshires 01266
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    Berkshire Farmhouse Vacation1 / 20
    (37)Excellent
    5 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Central Heating
    • Grill
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Mountain Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    We loved our stay at this lovely, peaceful home. The home is an excellent place to stay and the location couldn't be any better. The home was very clean and comfortable. We...
    Reviewed 26 February 2018
    We had a large group staying at the house with kids and had a great experience. Elaine is very thoughtful, helpful and attentive. She obviously cares about the house and makes...
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    About this property
    Quaint, , 2 story 1850's farmhouse in the Berkshires with original ceiling beams and 16' floor boards in much of the house. Fully furnished with 5 bedrooms, 2 full baths and a gorgeous screened-in porch overlooking 4 acres of gardens, stream and wooded mountains. Country kitchen with dish washer,...
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    West Stockbridge, Berkshires 01266
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 12
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    Apple Cottage1 / 10
    (5)Excellent
    3 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Wi-Fi
    • Mountain Views
    • Air Conditioning
    • Balcony
    • Parking
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 November 2018
    We stayed at the house for thanksgiving weekend — 1 couple each plus child in each suite and our mother in downstairs bedroom. House was ideal mix of informal rustic and luxury...
    Reviewed 25 July 2016
    Our family of four (two adults and a 12 and 8 year old) recently stayed at Apple Cottage with my sister who lives in Boston and had a wonderful week. The house was perfect for...
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    About this property
    Charmingly restored 1840 cottage in the apple orchard of a working organic farm. Completely renovated in 2015 with thoughtful amenities, fresh eggs and produce and acres of trails and views. Close to waterfalls and lakes. Nearby ski hills, Tanglewood concerts, theatre, film festival, dance and...
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    Sheffield, Berkshires 01257
    Holiday Rental House - 3 Bedrooms, 6 Bathrooms, Sleeps 8
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    Escape to the Berkshires!1 / 20
    (4)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 August 2016
    My family and friends - group of 8 just spent an amazing week at this home. The house was a perfect size, clean and fully stocked. We made gourmet breakfasts, lunches &amp...
    Reviewed 15 May 2016
    The Levy's home was perfect for our intergenerational family, including a 7month old grandaughter. We were pleasantly surprised by how well the home was supplied and organized...
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    About this property
    Come to the Berkshires and stay in one of the most beloved areas of Massachusetts. We are located close to Lenox, Stockbridge, Lee, Great Barrington and more. Our 3400 square foot ranch home is located in the heart of the Berkshires awaiting memorable times with your family and friends. Our...
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    Becket, Berkshires 01223
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    INTERIOR DESIGNERS BOTANICAL GARDENS1 / 34
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
    • Private Garden
    • Patio
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 August 2017
    We have been traveling to the Berkshires for several years to attend Shakespeare & Company plays. We have stayed at Inns and Hotels. This was our first time, in this area...
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    About this property
    AS YOU OPEN THE GATE FROM THE DRIVE YOU WALK ONTO YR FRONT DECK LEADING TO THE ENTRY , MUD ROOM WHICH HOLDS YR SUMMER NEEDS, SKIS AND BOOTS. THIS LEADS TO THE COTTAGE APT. [attached to the owner`s quarters} LIVING RM- HAS A SOFA SLEEPER TO ACCOMMODATE 2 MORE GUESTS. KITCHENETTE W/ LG CEILING...
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    Lenox, Berkshires 01240
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 5
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    Beautiful Vacation Home1 / 32
    (5)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Mountain Views
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Patio
    • Sauna
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 February 2017
    Our 4 families stayed here for a long ski weekend and had the best time! The home is beautiful-- and had plenty of space for all of us! The home was fully stocked with...
    Reviewed 10 November 2016
    Excellent experience. Very spacious and beautiful. Amazing backyard woods. Beautiful scenery within and around the town. Very attentive owners.
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    About this property
    We call this house ‘South Sedgwick’ because of its location on a piece of land formerly used by the Sedgwick family for picnicking–an ideal spot for relaxation with stunning views of Monument Mountain and Ice Glen. The house is newly constructed with ash hardwood floors, custom white pine trim and...
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Heart of Lenox1 / 10
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Garden
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 August 2018
    1/2 house, with owners in other half, which was handy for questions and suggestions. Very clean, and queen bed was really comfortable. Other BR has twin bedsKitchen has...
    Reviewed 28 May 2017
    Title sums it up! Excellent choice for our recent visit to Lenox. The house is very clean and comfortable and the owners are very accommodating. Location is great, just steps...
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    About this property
    Just rated Best Small Town in the Northeast by USA Today, our home is located in the heart of Lenox MA! Come relax in our lovely home, situated in a quiet neighborhood just steps from downtown. Walk to Zagat rated restaurants, shop unique boutique shops, hike in Kennedy Park. Whether you love the...
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    Lenox, Berkshires 01240
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Gem of the Berkshires, walk to downtown & lake.1 / 30
    (4)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Mountain Views
    • Patio
    • Grill
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 March 2018
    This home is a wonderfully appointed home, conveniently located just outside of town. It was perfect for our multiple family ski getaway. The owner is thorough in helping...
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    About this property
    This sparkling, newly renovated 3 floors house is for available vacation rental. A stunning sunrise & gorgeous view of the Berkshire Mountains. Conveniently located near many attractions, such as Tanglewood, Butternut ski, etc The house has an open floor plan, making each room flow into another....
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    Great Barrington, Berkshires 01230
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Washer
    • Grill
    • Wi-Fi
    • Patio
    • Air Conditioning
    • DVD Player
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The lakeside house is built on a 1.1 acre lot with view of Lake Garfield. It is only three minute walk to the public beach with life guards on site. In the summer, Jacob’s Pillow Dance Center and Tanglewood Music Center are about 25 to 30 minutes away. In the winter, Ski Butternut resort is about...
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    Monterey, Berkshires 01245
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    Heart of the Berkshires!1 / 12
    (2)Very good
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Private Garden
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 August 2017
    A friend and I rented this charming home for 3 nights. It was immaculate, the kitchen was well stocked, furniture/beds comfortable. The bedrooms had window a/c units. What...
    Reviewed 29 June 2017
    I was looking for a place for two couples for a weekend in the Berkshires, and stayed at this house. It was a perfect fit for my needs. The house is on a road that has very...
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    About this property
    This sophisticated ranch is privately sited on a premier road in Stockbridge. Less than a mile to Tanglewood, Stockbridge Bowl, and local theatre companies. Nestled between Lenox and Stockbridge, this is perfect location for your vacation. 3 bedroom and 1 bath, an open floor plan with the guest...
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    Lenox, Berkshires 01240
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Restored 1886 Eyebrow Colonial1 / 17
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Mountain Views
    • Patio
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Washer
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 January 2017
    Our family of four absolutely loved our stay in Melanie and Henry's home. After communicating with Melanie before our arrival, we felt welcome before we stepped into the house...
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    About this property
    Explore the culture and natural beauty of the Berkshires while vacationing in a completely restored colonial home with modern amenities. You will be central to all the wonderful cultural attractions and outdoor activities in the area. Walk to the quaint town of Stockbridge and the Norman Rockwell...
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Stockbridge Bowl - Beach Lake Cottage near Tanglewood (1.8 miles) & Kripalu1 / 24
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Mountain Views
    • Balcony
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 July 2018
    Great location, 2 minute walk to the beach with a view of the mountains and a very short drive to Tanglewood, Norman Rockwell Museum and all local attractions.Cindy and Paul are...
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    About this property
    Central Berkshire location! Walk across street to Stockbridge Bowl Beach Lake! Kripalu around the corner, Tanglewood only 1.8 miles to South Gate. Open layout, vaulted ceilings, exposed rafters, ceiling fans, fully equipped kitchen and amenities, washer & dryer. New hypoallergenic Mellanni...
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    Location Information
    Stockbridge, Berkshires 01262
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Quiet Comfortable Cabin 5 Min. Walk to Lake1 / 13
    (13)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Parking
    • Grill
    • Porch
    • Washer
    • Air Conditioning
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 February 2017
    The location was easy to get to (even in the dead of winter).The place was clean, spacious and exactly as described. The wood stove was a great heat source as it was really cold...
    Reviewed 26 October 2016
    A charming cozy cottage in a quiet setting with all you need for comfort included. We hiked, canoed and visited farms and museums close by. It was a lovely fall getaway!
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    About this property
    Remember the simple pleasures of a country, lakeside vacation where you can spend the day swimming or boating, exploring new towns and attractions, or just spending a lazy afternoon reading on the screened-in porch? Get back to those simple pleasures in our cabin, which is located in a beautiful,...
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    Becket, Berkshires 01223
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Country Elegance in the Berkshires1 / 22
    (2)Excellent
    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Parking
    • Grill
    • Outdoor Dining Area
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    • Internet Access
    • Shared Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 September 2018
    We rented this house for our family coming together in celebration of my Brice getting married.mu sister showed up to the Home first but she was sure she was at the wrong place...
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    About this property
    This immaculate home is the place for relaxing, entertaining and sharing great times with family and friends. The house sets over 4 beautifully wooded acres. We call it the 'illision of seclusion,' as it is very private and yet is 5 minutes from the town as well as lakes, hiking, movies, theater,...
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    Great Barrington, Berkshires 01236
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 12
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    Family-friendly Cottage Near Lake, Tanglewood1 / 16
    (6)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Cable/satellite TV
    • Porch
    • Parking
    • Washer
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 August 2017
    Location was fantastic. Sarah (the owner) provided some great advice on local farmers markets and hikes. The beach was a quick walk from the cottage where we could paddle on...
    Reviewed 31 July 2015
    This was a wonderful place to spend a family vacation. The house is immaculate, functional and well furnished. The proximity to all of the many venues and activities the area...
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    About this property
    Located a short walk to the town beach on the Stockbridge Bowl, and 1.5 miles from Tanglewood's Hawthorn entrance, this casual summer cottage is a great get away for the whole family. The master bedroom is equipped with a queen bed; two twins in the 2nd bedroom, and a full-size bed in the 3rd...
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Lake House1 / 18
    (4)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 9 Quick View
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    • Washer
    • Wi-Fi
    • DVD Player
    • Sauna
    • Air Conditioning
    • Grill
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 September 2016
    My family and I traveled to the Berkshires from Boston and stayed in this gorgeous lake house. We had booked vacation rentals in the past and had a whole range of experiences...
    Reviewed 2 September 2016
    We stayed at the Lake House on beautiful Laurel Lake with my family of 5 (two daughters, son, and my wife). We had an awesome time. The owners Marjorie and Frank were wonderful...
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    About this property
    Custom designed Furnished Lake House in The Berkshires in Massachusetts on the Lee/Lenox line. Gorgeous western sunsets ! The home has 4/5 bedrooms and one is equipped as a nanny suite or teen haven. It is close to skiing, golf, outdoor sports, shopping, and all cultural venues. It is located...
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    Location Information
    Lee, Berkshires 01238
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 9
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    Berkshires Spacious Comfortable Charming Farmhouse1 / 12
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Mountain Views
    • Air Conditioning
    • Parking
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 June 2013
    This property was a great home base for our brief visit to the Berkshires. Plenty of space and well equipped. We especially enjoyed the beautiful property, whether sitting on...
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    About this property
    Experience a little of old New England. Our vacation rental is a charming historic family farmhouse apartment with lots of room and comfort,2100Sq.ft., situated on 22 acres. Built in 1782, our farm was famous for breeding Plymouth Barred Rock chickens. In the 1800's, one of these barred rock...
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    Location Information
    Lee, Berkshires 01238
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Shaker Hill1 / 27
    (2)Average
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Porch
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • Mountain Views
    • DVD Player
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 September 2014
    This is a very large house, more than adequate in size for a group of ten people. It has a big yard and a spectacular view of the mountains, especially from an upstairs window...
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    About this property
    Shaker Hill is a quirky rambling farmhouse located less than 3 hours from NYC and Boston. Hidden away down a 400’ unpaved driveway on 30 acres of fields and forest in the heart of the Berkshires, Shaker Hill is totally private and surrounded by 30 acres of rolling fields, diverse wetlands,...
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    Location Information
    Great Barrington, Berkshires 01230
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Wyndham Bentley Brook Resort Rents-Hancock,MA -Jiminy Peak1 / 10
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Shared Indoor Pool
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 February 2018
    Staying in a ski in/out cannot be topped. This place was family friendly, so easy to navigate and the staff was SUPER helpful throughout the entire weekend. We have a 3 year old...
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    About this property
    Lodging at the highest rated resort at Jiminy Peak Mountain--Wyndham Bently Brook Resort-Mountainside What is Jiminy Peak Known For---The Best Skiing in the Berkshire Mountains tucked away in Hancock, Ma. 2 Bedroom Unit consisting of-King bed master, 2 doubles 2nd bedroom and a queen sleep...
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    Location Information
    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Balcony
    • Air Conditioning
    • Parking
    • Mountain Views
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located along the Appalachian trail and 3 miles to Great Barrington, this designer home is central to all the Berkshires has to offer, not to mention being 35 minutes to Hudson you are really in the center of of it all. This completely separate designer home is located on the 2nd and 3rd floors...
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    Location Information
    Sheffield, Berkshires 01257
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Sauna
    • Wi-Fi
    • Hot Tub
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Complete your Berkshires retreat with a stay in the spacious Studios, perfect for romantic couples and small families. Suites feature plush bedding, additional sleeper sofa and fully equipped kitchen for all your dining needs. Minimum age to check in is 21 Daily housekeeping is not included and...
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    Location Information
    Hancock, Berkshires 01237
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2200sf Country House on 16 Acres-2 Miles to Jiminy1 / 14
    (3)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Mountain Views
    • Grill
    • Cable/satellite TV
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    • Washer
    • Internet Access
    • Central Heating
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come and enjoy our beautiful mountain retreat - A home for every season. This charming home away from home is a wonderful place for family, friends and romance. Only 3 minutes from Jiminy Peak! With over 2200 square feet, this new country home has plenty of space for everyone yet a very cozy...
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    Location Information
    Hancock, Berkshires 001237
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    The Gatehouse on Golden Hill1 / 13
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
    • Secure Parking
    • Private Garden
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 October 2017
    Stayed for 4 nights. Very spacious and well maintained. Greeted by Peter with prosecco, cheese, crackers,tomatoes, mint from the garden, and donuts. He gave us an orientation...
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    About this property
    We are located in the heart of America's cultural epicenter known as the Berkshires. Known as the 'Gatehouse' to upscale Erskine Park, this truly one of a kind Craftsmen inspired home is filled with unique features and materials seldom found including eucalyptus and Brazilian Cherry flooring,...
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    Location Information
    Lee, Berkshires 01238
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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    Writer's Room at Chestnut Lodge1 / 8
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Outdoor Dining Area
    • Mountain Views
    • Air Conditioning
    • Hot Tub
    • Balcony
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 June 2014
    We have taken the Writer's Room each Summer for about three years now. We find the Lodge to be authentic New England... our natural wood room to the rest of the house. It is...
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    About this property
    The Writer's Room is at the top of the stairs on the right. This handsome room is made completely of wood. Ceilings are higher and there's a sitting area in the big dormer. dormer faces east and get the morning sun! The floors are wide plank cherry milled from the property. the walls are pine....
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    Location Information
    Lee, Berkshires 01238
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Enjoy the Appalachians At Bentley Brook!1 / 21
    (1)Terrible
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Parking
    • DVD Player
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bentley Brook Surround yourself with the natural beauty of Massachusetts at Bentley Brook. Situated at the bottom of Jiminy Peak in the stunning Berkshires, Bentley Brook is the ski enthusiast dream come true. Ski out your door and straight to the resorts ski lift. Spend a day out on the world...
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    Location Information
    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Romantic Berkshire Cottage on Storybook Estate1 / 10
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Balcony
    • Terrace
    • Cable/satellite TV
    • Outdoor Dining Area
    • Internet Access
    • DVD Player
    • Parking
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 August 2017
    What a wonderful, magical place, heaven on earth! From the moment we were greeted warmly by Denise and entered our Tiny House, we knew this was such a special place.The sound of...
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    About this property
    Charming, One Bedroom Cottage, former sculpting studio on the Santarella Estate in Tyringham, MA. Known as the 'Silo Studio', there is a bedroom with queen bed upstairs, sitting room, wet bar with Micro/Fridge and bath downstairs. Fall asleep to sounds of babbling brook and views to pond and forest...
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    Location Information
    Tyringham, Berkshires 01264
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    chestnut lodge Queens Room1 / 2
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 August 2015
    I had the pleasure of staying at the Chestnut Lodge in the Queen's room. From the moment you step into the foyer you are taken back to a simpler time in this historic lodge. The...
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    About this property
    Sunny, light , bright and wide! the queens room is one of the biggest rooms and has private ensuite bathroom with tub/shower. 2 big closets, large writing desk, comfy conversation area, 2 dressers full sized bed. a section of the room has original ceilings so persons taller than 6'2' would be...
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    Location Information
    Lee, Berkshires 01238
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Retreat in the Woods1 / 6
    (6)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • DVD Player
    • Grill
    • Hot Tub
    • Parking
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 July 2017
    My husband and I vacationed in the Berkshires to hike and visit the MA state parks. This home is conveniently located within a 30 min. drive to many state parks and hiking...
    Reviewed 20 July 2017
    Lovely home - the pictures don't fully do it justice! The house is shielded from the road and set in a small clearing, so it gets plenty of light and a pleasant breeze at night...
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    About this property
    Located in a quiet corner of the northern Berkshires, this lovely two-bedroom home has a combined living room/kitchen with cathedral ceilings and a spacious bathroom complete with a 2-person jacuzzi tub. The house is located about a mile from beautiful Tannery Falls in the Savoy State Forest and...
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    Location Information
    Savoy, Berkshires 01256
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Wyndham Bentley Brook at Jiminy Peak1 / 21
    (10)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Skiing: Property Is In A Ski Resort
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Internet Access
    • Hot Tub
    • Sauna
    • Shared Indoor Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 December 2017
    Great time went to check out the foliage resort was clean, staff friendly and helpful. Unit was spacious and clean. I could only imagine how great of a place it would be to ski...
    Reviewed 23 March 2015
    This is such a great property. We had a one bedroom unit which was still sufficient for 2 adults and 3 teens. Gorgeous large double bedroom with full bath and murphy bed and...
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    About this property
    Wyndham Bentley Brook Rental includes: King bed master, 2 doubles in the 2nd bedroom, queen sleep sofa, full living room, dining room and kitchen with utensils. New York + New Jersey Flock to Hancock Mass/Jiminy Peak Ski Area, rated Top 5 Family Mountains in the Northeast! Wyndham Bentley Brook...
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    Location Information
    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Wyndham Bentley Brook Resort ~ 2 Bedroom, Sleeps 61 / 23
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • DVD Player
    • Cable/satellite TV
    • Sauna
    • Skiing: Property Is In A Ski Resort
    • Shared Indoor Pool
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 October 2018
    This resort is in a beautiful setting, The reception area is large warm and welcoming and the decorations for Halloween were amazing.The Pool was out of action when we stayed as...
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    About this property
    ** Please email or call to confirm availability. Ski-In/Ski-Out Resort! Wyndham Bentley Brook is located right at the base of Jiminy Peak ski mountain, with ski lifts only 200 feet from the resort's front door. In winter, you can ski right out the door to the lifts. In spring, summer and fall,...
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    Location Information
    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Mountain Views
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This vacation home has something for everyone! If you're a culture vulture, outdoor enthusiast, or just want the peace and quiet of the country, this 4 bedroom home in the Berkshires is for you! It is 15 minutes from Lenox and Tanglewood, 10 minutes from shopping, restaurants and several theatres,...
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    Location Information
    Richmond, Berkshires 01254
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    1 Bedroom, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Parking
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bentley Brook Surround yourself with the natural beauty of Massachusetts at Bentley Brook. Situated at the bottom of Jiminy Peak in the stunning Berkshires, Bentley Brook is the ski enthusiast dream come true. Ski out your door and straight to the resorts ski lift. Spend a day out on the world...
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    Location Information
    Hancock, Berkshires 01237
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 8
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    Enjoy horses and the largest recreational lake in Massachusetts1 / 20
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • Hot Tub
    • Parking
    • Wi-Fi
    • Grill
    • Terrace
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 November 2018
    I stayed here with a few friends looking to escape the city for a cozy weekend away. Wendy ad Kevin were amazing and went above and beyond their responsibilities as hosts. Wendy...
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    About this property
    Enjoy the beautiful Berkshires. Watch the horses roam. Have a guided trail ride (additional fee) or have a camp fire only feet away from the horses. Within steps from your accommodations, enjoy the largest recreational lake in Massachusetts. Bring your boat or jetski. Or use our row boat. Go...
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    Location Information
    East Otis, Berkshires 01029
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Parking
    • Mountain Views
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One bedroom, one bathroom cottage on beautiful country road. Private garden and screened-in porch. Two miles to shops and restaurants of downtown Great Barrington. Enjoy nearby skiing, cycling, fishing, hiking and golf. The Space: Quaint cottage with wood burning stove. Ideal base for enjoying...
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    Location Information
    Great Barrington, Berkshires 01230
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Patio
    • Grill
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    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly renovated contemporary house on 2 acres in Stockbridge. Great space surrounding house for outdoor sports and sitting around the fire at night. 3 bedrooms, 3 bathrooms, indoor fireplace, wood floors, many windows and closets. Large kitchen. WiFi. Master bedroom has king bed and master...
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    Stockbridge, Berkshires 01238
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Mountain Views
    • Air Conditioning
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THIS CUSTOM BUILT HOME is a one-of-a-kind, must see getaway retreat that is beautifully furnished, and meticulously maintained. The entire first floor 'guest suite' was designed to accommodate friends or extended family. The upper level is the main floor with an open plan kitchen, dining room, and...
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    Location Information
    Stockbridge, Berkshires 01262
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Waterfront
    • Mountain Views
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Get away from it all at our beautiful Berkshire lakefront wooded retreat. Swim, canoe, kayak, sunbathe, play tennis during the day, then enjoy the evening a short drive away at Tanglewood, Jacobs Pillow, or perhaps go to the movies in Great Barrington. Have dinner at the Red Lion Inn, or one of the...
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    Location Information
    Monterey, Berkshires 01245
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 6
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