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Holiday Rentals in Manchester-by-the-Sea

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    All 182 Rentals in Manchester-by-the-Sea
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    Manchester-by-the-Sea
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Manchester-by-the-Sea
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Manchester-by-the-Sea
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Manchester-by-the-Sea
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful three bedroom vacation home is in the heart of Manchester-by-the-Sea. On a quiet side street, it's just a short stroll to the picturesque harbor, shops, restaurants and beaches that make this town one of the most sought after vacation destinations on the North Shore. Recently...
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    Manchester-by-the-Sea, Cape Ann 01944
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Manchester-by-the-Sea
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Booth Cottage Ocean view, private path to beach. Private mowed path, ten minute walk to village, harbor, 2 parks, on the commuter rail, four bedrooms, three full and one 1/2 bath, extra large lawn for ball playing, large porches, high ceilings, large windows. 3000$ per week, lower rates off...
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    Manchester-by-the-Sea, Cape Ann 01944
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Manchester-by-the-Sea
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
    • Wi-Fi
    • Grill
    • Patio
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Cottage was built in the 1920s and recently renovated. At the end of a long driveway on the back of an old estate, it is very private and yet within 10 minutes walk of Singing Beach and less than a mile from the town of Manchester. So there is easy access to shops, restaurants, and even...
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    Manchester-by-the-Sea, Cape Ann 01944
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Manchester-by-the-Sea
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Completely renovated 3-4 bedroom, 1.5 bath. Spacious designer kitchen w/ stainless steel appliances. Large Living room, Dining Room, Family Room (optional bedroom) (first floor) and three bedrooms (second floor). Close to town center, commuter rail, and Singing Beach. 4 minute drive to Singing...
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    Manchester-by-the-Sea, Cape Ann 01944
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 7
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    The following rentals are within 15 kilometres of Manchester-by-the-Sea.
    Romantic SUMMERWIND COTTAGE- Scenic Harbor View1 / 26
    (17)Excellent
    Gloucester
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • Secure Parking
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 August 2017
    We had a fantastic holiday in Gloucester. Summer wind was the perfect location - the house was beautiful, with all mod cons and fabulous views over the harbour. It was also...
    Reviewed 25 May 2017
    We recently stayed at Summerwind Cottage in Gloucester MA. We thoroughly enjoyed our stay. The decor was wonderfully New England cottage. The living area was cozy with lots...
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    About this property
    Picture a romantic, seaside cottage with a lovely large deck, set on a hillside overlooking the harbor... catching the summer wind, salt air and sounds of seagulls as they drift up from the harbor. Open living space - large living room with sliding door onto large private deck overlooking the...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    GULLY POINT AT THE SEAWARD EXUDES CLASSIC COASTAL CHARM1 / 18
    (2)Excellent
    Rockport
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Grill
    • Ocean Views
    • Air Conditioning
    • Patio
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 July 2016
    The Seaward is the perfect getaway! I travelled from Boston to Rockport to take a little break from the city with my boyfriend. It's about a 50 minute drive or you can take the...
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    About this property
    Formerly Seaward Inn, 'The Seaward' continues to offer a spectacular setting and charming accommodations. Here you can fully relax while listening to the ocean waves. Experience the charm, serenity, and unspoiled beauty that is The Seaward. Suite 205, also known as Gully Point, offers...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Gloucester Harborscape View 1 & 1/2 BR; walk to beach & town1 / 42
    (10)Excellent
    Gloucester
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Ocean Views
    • Grill
    • Balcony
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 May 2018
    Mark's rental apartment in Gloucester is my all-time favorite rental home! It offers a comfortable queen-sized bed, an additional bedroom with a twin, a living room with a small...
    Reviewed 6 October 2017
    When we arrived our host met us at the door and let us in, the first thing we noticed was the wonderful view and a balcony to sit on. We were close to most places by walking.
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    About this property
    Reservations from June 22 to end of September must be for 7 nights minimum with Check-in on Friday afternoon. The view is spectacular! The apartment is inside a commercial marine building so it's right on top of the water, where the ships come in to unload lobsters and other catches. The...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Rockport
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Building was once the historic Sail loft- oozing with character and charm. Inside is a 2 Bedroom, 1 Bath apartment unit. A good sized living area with a leather couch, TV & dining table that can fit up to 6. There is a small patio in front with a table, bench and 2 chairs. Great views of White...
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    Rockport, Cape Ann 01966
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Periwinkle Cottage - Unit 11 / 23
    (33)Excellent
    Rockport
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Washer
    • Wi-Fi
    • Outdoor Dining Area
    • Parking
    • Cable/satellite TV
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    June 22, 2018As two old Englanders’ visiting New England we have had a wonderful week here. We last visited 10 years ago in November, so needless to say, the weather has been...
    Reviewed 23 May 2018
    My husband and I rented the cottage for a short getaway after our wedding in Kennebunkport, Maine. After the hubbub of the wedding, it was nice to have this quaint cottage to...
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    About this property
    OPEN YEAR ROUND - 2 night minimum stay. 2018... we're honored to celebrate our 9th year hosting guests from all over the world! PERIWINKLE COTTAGE - truly a place to call 'a home away from home'. This 2-unit, townhouse cottage offers guests privacy and an updated seaside decor with today's...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    The Harborfront, Beverly/Salem, Boston North Shore1 / 26
    (4)Excellent
    Beverly
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Balcony
    • Parking
    • Waterfront
    • Wi-Fi
    • Porch
    • Air Conditioning
    • Grill
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Husband and I enjoyed our 2 nights here and wish we could stay longer. As usual, Kathy thinks of all the amenities a guest could need—including luxurious toiletries and plush...
    Reviewed 21 September 2017
    Excellent stay: very good reception and coordination. A very nice stay in comfortable apartment. View from 3rd floor was great. Kitchen well supplied. Convenient location.
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    About this property
    Welcome to the Harborfront House, located at historic Independence Park and Beach on Lothrop Street, recently recognized by the Boston Globe as one of the “20 Best Streets in Boston and Beyond'. You will be instantly captivated by the waterfront activity just steps from the front...
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    Beverly, Massachusetts 01915
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Family Friendly Apartment, Short Walk to Beach/Downtown, Parking, WiFi, Grill1 / 21
    (5)Excellent
    Rockport
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Patio
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Grill
    • DVD Player
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 June 2016
    We really enjoyed our stay. Originally from Massachusetts, we looked for a place that would be interesting and relaxing. The rental is perfect. We were comfortable, had...
    Reviewed 19 February 2016
    With two bedrooms, a convenient, well-stocked kitchen, and a homey living room, the Salty Dog was just what we needed for a family getaway to Rockport, MA. Owners were friendly...
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    About this property
    The Salty Dog Summer Stay is a spacious, bright, furnished apartment with all the comfort and amenities one may need to enjoy time in our seaside town. Perfectly located on Atlantic Avenue in the Old Garden Beach neighborhood, many of Rockport's shops, restaurants, and attractions are a short walk...
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    Rockport, Cape Ann 01966
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    Waterfront 2 Bedroom !1 / 14
    (5)Excellent
    Gloucester
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Internet Access
    • Waterfront
    • Air Conditioning
    • Balcony
    • Washer
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 January 2018
    We stayed here for a family wedding in Sept. 2017. The apartment was a perfect location(wedding was 8-mns away). It was very well maintain and very,very clean. (Which is our No...
    Reviewed 2 May 2017
    This apartment is located on the water. When I say "on the water", that's exactly what I mean. At high tide, looking down from the balcony you see water. There are...
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    About this property
    Vacation at the very edge of the Gloucester Inner Harbor watching the boats and ships passing by. Relax on your private deck over the water and enjoy this extraordinary picturesque setting that can't be matched anywhere on the harbor ! Whale watching or trips around harbor by boat is all within...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Charming 2 bedroom Rockport Carriage House1 / 14
    (9)Excellent
    Rockport
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Parking
    • DVD Player
    • Patio
    • Shared Garden
    • Washer
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 October 2014
    We stayed in this fantastic house for over a week with my husband, my sister and her husband. What a wonderful find and what a beautiful place Rockport is. Cannot recommend it...
    Reviewed 4 August 2014
    We stayed in this lovely two bedroom home for two weeks and enjoyed every minute. The location was convenient to down town and various walking trails as well as the other...
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    About this property
    Rockport, a part of Cape Ann, is one of the most scenic towns in Massachusetts located on Boston’s North Shore, Rockport and nearby Gloucester are filled with attractions: art, music, shopping, beaches, whale watching, boating, fishing, bicycling… you name it! Historic Lexington, Concord & Boston...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    ChestnutSweet, for a sweet New England get-away!1 / 25
    (46)Excellent
    Marblehead
    2 Bedrooms, 2 Bathrooms, Sleeps 3 Quick View
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    • Secure Parking
    • Washer
    • Cable/satellite TV
    • Housekeeping Included
    • DVD Player
    • Patio
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    We returned to Chesnut Sweet for our 4th visit and continue to be amazed at the attention to detail in anticipating our every need. The Sweet is in a perfect location that...
    Reviewed 28 May 2018
    Great accommodation with excellent design, finish and very well maintained Marblehead is a lovely town with great views, bars and restaurants The owners were very friendly and...
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    About this property
    Chestnut Sweet, in Marblehead's historic Shipyard neighborhood, is a romantic, private hideaway offering new, top-drawer cottage furnishings and services, easy access to town and beach, and hosts who will welcome you like family. We're within sight, sound, and salt-water air of the ocean for guests...
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    Marblehead, Massachusetts 01945
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 3
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    NEW!  STUNNING STUDIO w/Scenic Harbor View1 / 19
    (3)Very good
    Gloucester
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Balcony
    • DVD Player
    • Air Conditioning
    • Secure Parking
    • Grill
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 November 2017
    Lovely apartment, with bonus deck for enjoying a BBQ & wine. Views of the working harbor can be enjoyed right from the bed (which is super-comfy!). Well equipped kitchen, all...
    Reviewed 24 November 2017
    One of the best vacations I've had in years. The owners were charming and attentive but also respectful of my privacy, which is important to me as a writer. The deck was a...
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    About this property
    Nestled on a hillside overlooking Gloucester's scenic harbor... enjoy magical sunsets, dining al fresco, twinkling harbor lights, and warm summer winds from the deck of this romantic getaway. This property is best described as a “studio plus”, featuring 3 separate rooms (400 sq. ft.): Bedroom with...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Captain Quarters1 / 14
    (3)Excellent
    Rockport
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Washer
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    • DVD Player
    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 July 2017
    We stayed for three nights over the July 4th holiday. Perfect location for walking to most places. There is parking right next to the house which is a real bonus in Rockport...
    Reviewed 2 July 2017
    We stayed in the Captain's Quarters of Changing Tides Bed and Breakfast for four nights. THe room's skylight greeted us each morning with blue skies filtered through the...
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    About this property
    Captain's Quarters,at Changing Tides Bed and Breakfast, features a queen-sized bed, two skylights and a shared bath, sleep well and look forward to a gourmet breakfast. Beaches, downtown shops and galleries are all within a short walk of our home. This room is located in the front of our home....
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    Rockport, Cape Ann 01966
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Quaint Seaside Village Studio Steps  From Beach1 / 12
    (5)Excellent
    Rockport
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Grill
    • Balcony
    • Outdoor Dining Area
    • Porch
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 March 2017
    We so much enjoyed this cozy little apartment! It is a great find and well kept with everything you need to enjoy your stay in Rockport. Walk to Bearskin Neck in the heart of...
    Reviewed 21 September 2015
    My husband and I stayed in the studio and loved it. The location is great. You are near all the shops in town and the beach is a block away. The train station is nearby and...
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    About this property
    BOOKING ACCEPTED NOW FOR SUMMER 2018!!. DEDICATED OFF-STREET PARKING FOR ONE CAR. BEST LOCATION IN ROCKPORT steps away from everything! Ground floor studio boasts comfortable and clean efficiency with AC, cable TV and microwave kitchenette, private entrance, private bathroom all on the ground...
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    Rockport, Cape Ann 01966
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedroom Cottage on the Beach!1 / 17
    (5)Excellent
    Rockport
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Ocean Views
    • Cable/satellite TV
    • Outdoor Dining Area
    • Parking
    • Waterfront
    • Wi-Fi
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 June 2017
    We all had a wonderful stay at this ocean front home. The home was very clean and comfortable. The location is great! We had 7 people staying and they all loved it there! The...
    Reviewed 6 October 2014
    We rented this quaint, pretty cottage to celebrate a birthday weekend. Our only complaint is that we didn't have more time to spend here. Jennifer was great to work with-very...
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    About this property
    Sitting directly on picturesque Long Beach, this is the perfect spot for a romantic get-away or a family retreat. With decks in the front and back of the house, sun-chasers and shade-seekers alike will be pleased at any time of day. The cottage is sunny and open with a large eat-in kitchen and...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 7
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    Rockport
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Ocean Views
    • Terrace
    • Waterfront
    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Seaward offers a spectacular setting and charming accommodations. Loblolly Cove, offers accommodations for up to 4 people. One bedroom has a queen sized bed, while the rather spacious living room has accommodations for two more. At Loblolly Cove, you will enjoy a deck with ocean views and...
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    Rockport, Cape Ann 01966
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    La Boheme RETREAT Studio1 / 26
    (3)Very good
    Gloucester
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
    • Wi-Fi
    • DVD Player
    • Waterfront
    • Patio
    • Central Heating
    • Ocean Views
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 September 2016
    This unit was a great location! It was easy to get to the train to go into Boston as well as to travel to other sites in and around Boston. My daughter and I loved to sit on the...
    Reviewed 27 January 2015
    I had a chance to stay at this wonderful studio for 2 weeks and couldn't my believe good luck. This property, a former Unitarian Church and sexton's residence, has been...
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    About this property
    UNPLUG, UNWIND & UPLIFT your spirits! No TV (wifi only). For those seeking to truly rest, relax, rejuvenate and contemplate their journey on earth. Step back in time with this 60's Boho, funky-style studio. Creative objets d'art and romantic lighting creates a very cozy, dark atmosphere (a...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Salem MA efficiency on quiet dead end street near historic downtown and college1 / 11
    (2)Excellent
    Salem
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Internet Access
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 April 2018
    As soon as I flicked on the lights, I knew that this apartment was just what my wife and I needed: affordable, within walking distance (20 min.) to downtown, and comfortable. I...
    Reviewed 10 October 2017
    My brother and I stayed at this cozy little apartment for an extended weekend. The location was perfect. We enjoyed a easy walk from downtown Salem to our place every day. The...
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    About this property
    Brand new listing...Be the first one to stay on the second floor of our two family house and give the first review. I am their daughter and live on the first floor. My parents decided to change part of their living quarters into the latest Air B&B. The rooms are very clean. The house has been...
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    Salem, Massachusetts 01970
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Back Beach1 / 15
    (2)Excellent
    Rockport
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Wi-Fi
    • Private Garden
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 July 2017
    House was wonderful and location perfect. Three generations spending a week making memories and no one was disappointed. Smoke detector battery issue (not something ever...
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    About this property
    Cozy, bright , and ideally located. Unrestricted view of ocean from back of house and large deck. Walk across to Back Beach, 5 minute walk to Front Beach and Main Street downtown. Large fenced yard across from ocean. Beautiful sunrises and sunsets. Train Station 1/2 mile down Granite Street for a...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Rockport
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Grill
    • Ocean Views
    • Waterfront
    • Wi-Fi
    • Balcony
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This newly renovated ocean view apartment at the Seaward exudes classic coastal charm. Here you will fully relax while listening to the ocean waves. Lover’s Cove features exposed brick walls, newly conditioned hardwood floors and a king bed. This seaside apartment makes for our most spacious...
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    Location Information
    Rockport, Cape Ann 01966
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Rockport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    About this property
    This spacious seaside apartment offers 2 bedrooms, 2 bathrooms, and living room/kitchen with a sunny ocean view dining/game area within a bay window. At over 800 square feet it is our largest accommodation. You’ll enjoy Gap Cove’s seaside charm, with amenities including free WIFI, DVD player,...
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    Rockport, Cape Ann 01966
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Ipswich
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
    • Cable/satellite TV
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    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Set upon Great Neck hill, this antique winterized cottage has a great ambiance and a nice view of the water where the Atlantic meets the mouth of Ipswich River. Spacious and fun for families and small groups, you can walk right down to Pavilion Beach within 10 minutes and access to famed private...
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    Ipswich, Massachusetts 01938
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Rockport
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Air Conditioning
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    • Waterfront
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    • Ocean Views
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spruce Cottage at The Seaward offers a spectacular ocean view setting and charming accommodations. Spruce Cottage, is a quaint and cozy two bedroom cottage with ocean views & fireplace. It has a private queen bed in one room and two twin beds in the other. The living room has a kitchenette and...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Lovely 'Blue Heron Cottage' on Annisquam River!1 / 24
    (1)Excellent
    Gloucester
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Ocean Views
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 July 2017
    We walked to the beach at Good Harbor and enjoyed crossing the sandbar at low tide to Salt Island. Two grocery stores, liquor store were very close. Gloucester had a small...
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    About this property
    Enjoy a peaceful retreat in coastal New England by staying at 'Blue Heron Cottage' - a lovely 3-bedroom, 1-bathroom Gloucester vacation rental cottage, which sleeps 6! Featuring a bright and welcoming interior, splendid waterfront views and terrific access to nearby beaches, this residence will...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Cozy Rockport Cottage with Ocean Views1 / 14
    (1)Excellent
    Rockport
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • DVD Player
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    Pet friendly
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    Reviewed 25 August 2016
    This simple seaside cottage is well situated to some lovely views of the coast, including the light houses of Thatcher Island. The cottage itself is well-maintained with a very...
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    About this property
    Walk to the water from this cozy peaceful cottage with ocean views. This bright and cheerful recently updated vintage cottage is just minutes from nearby beaches. Enjoy beautiful sunrises, birds chirping, and leisurely strolls along the rugged coast. Stunning views of the Thacher’s Island Twin...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Ocean Front Cottage on Scenic Long Beach1 / 26
    (6)Excellent
    Rockport
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ocean Front Cottage Directly on the Boardwalk of Scenic Long Beach - Cape Ann, MA Ocean front-row cottage (152 Long Beach) has a 270-degree ocean front view and is the last house facing east on the boardwalk of beautiful & sandy Long Beach. Location allows full views of the twin lighthouses of...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Relax and enjoy the summer in Marblehead1 / 16
    (2)Excellent
    Marblehead
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Parking
    • Outdoor Dining Area
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 June 2017
    What a lovely, homey place to stay for 4 adults and 2 children! A beautiful home, well furnished, tastefully decorated, clean and cozy, in a quiet neighborhood. Plenty of...
    Reviewed 15 August 2015
    Wow! Great summer stay and family reunion in Marblehead, thanks in no small part to this absolutely pristine home. The photos do NOT do this home justice. The feel is...
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    About this property
    Located only three blocks from Devereux beach and ln a quiet neighborhood, our house, renovated in 2014, is the perfect getaway for the summer. It is walking distance to downtown Marblehead, restaurants to a movie theater...The house, fully renovated in 2014 can comfortably accomodate 6 people. The...
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    Marblehead, Massachusetts 01945
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Gloucester
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gloucester Waterfront Waterfront Vacation House with Dock Direct riverfront home with dock overlooking Annisquam River, Lobster Cove, Wingaersheek Beach, and out towards Ipswich Bay. Open living spaces with endless views of both the river and marshland. This is true waterfront living! So...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Beachcomber Suite1 / 11
    (2)Very good
    Rockport
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 July 2017
    Fabulous food was awesome, she even irons the sheets! Highly recommend staying here. The breakfast was delicious.
    Reviewed 20 July 2016
    It was wonderful to be with Stephanie and Jay - their home is beautiful and welcoming. Stephanie's breakfast is not to be missed! I especially enjoyed the outdoor spaces - the...
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    About this property
    Beachcomber Room, at Changing Tides Bed and Breakfast, features a comfortable king sized bed or 2 twin beds, and an ensuite bathroom. This sunny room has 2 sky lights, a ceiling fan, AC, a sitting room with a small refrigerator, and a shared bathroom. Stay includes daily multi-course gourmet...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Marblehead
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
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    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on Marblehead Neck, just a short walk to the harbour, you'll find all you need to enjoy a luxurious stay in this grand New England home. All the comforts you need are provided in a clean and functional home. Top quality outfitting for everything. I'll personally make sure you have all you...
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    Location Information
    Marblehead, Massachusetts 01945
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    Gloucester
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This large and comfortable vacation home is just steps from the white sands of Long Beach--a perfect summer location! Built in the early 1900's, much of its early charm still remains but is augmented with an updated kitchen and many amenities. On the ground floor there is living room with plenty...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    Cozy Beach Cottage in Marblehead1 / 21
    (1)Excellent
    Marblehead
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 October 2017
    The owners were very accommodating, and the ocean is a few houses down the road which made a lovely walk to watch the sunrise and the sunset. It was relaxing sitting in the back...
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    About this property
    Come enjoy our 3 bedroom Marblehead home located in a quiet, private neighborhood that is full of sun. Just a few houses down from Salem Harbor, the house is situated near a boating beach where you can enjoy the beautiful views or take a kayak out right into the harbor. Beautiful swimming beaches...
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    Location Information
    Marblehead, Massachusetts 01945
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    Waterfront Woodsy 3BR Cottage1 / 12
    (1)Excellent
    Gloucester
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Private Garden
    • Waterfront
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 August 2017
    Our family of 4 (plus two standard poodles) thoroughly enjoyed our stay at this charming spot in the Lanesville section of Gloucester. The sunsets are spectacular, it's very...
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    About this property
    Imagine yourself walking across the lawn to the ocean, sweetly lapping the rocks. You take off your sandals and put your feet into the cool water. Second thought, jump right in! Great space for activities; near beaches, restaurants, galleries. The Space This cottage has been hosting travelers and...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Vintage Home directly on the Annisquam River1 / 12
    (2)Very good
    Gloucester
    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Porch
    • Internet Access
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Waterfront
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 November 2014
    We had a great time. A couple things you might find helpful. There is a shower in the basement bathroom. This house is not handicapped friendly. All the bedrooms are upstairs...
    Reviewed 7 July 2013
    House is fully equipped with everything you could possibly need. Views are spectacular. Sleeping arrangements are comfortable
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    About this property
    This six bedroom comfortable house has a large full equipped kitchen with two seating areas. The livingroom has wicker furniture and a stone fireplace. Enjoy the large wrap around deck watching the boat activity from sun up to sun down. Park of the wrap around porch is covered which is great for...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    Gloucester
    5 Bedrooms, 2 Bathrooms, Sleeps 13 Quick View
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    • DVD Player
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    **There is a possibility that construction will ongoing near the property during the summer of 2016** Welcome to your very own summer beach home! Located across the street from the North Shore's best beach, this two family home offers five bedrooms, two bathrooms, two separate living spaces as...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 13
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    Dragonfly1 / 7
    (2)Excellent
    Gloucester
    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Wi-Fi
    • Outdoor Dining Area
    • Secure Parking
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    • Private Garden
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 September 2016
    A big, comfortable home, surrounded by woods, a short walk to the ocean, and a short ride to downtown Gloucester or Rocky Neck. A beautiful, well appointed place. Home for a...
    Reviewed 30 August 2016
    The Dragonfly is a great place to stay for a big group! It is a beautiful home, with so much character and is clearly well loved by Patricia, the owner. It is even better than...
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    About this property
    Spacious home located two blocks from Atlantic Ocean and close to wedding venues including Elks, Cruiseport, & Anninsquam Yacht Club. 7 day minimum stay Sat. To Sat in July & August. Large modern fully equipped kitchen with double oven, 5 burner Viking cooktop, dishwasher, washer, dryer. Three...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 11
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    Gloucester
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    This comfortable recently renovated 3 BR vacation home is conveniently located a block away from Gloucester's scenic outer harbor. You'll love being just steps away from Gloucester's historic Stage Fort Park, once a landing place for pirates, now home to two public beaches, tennis courts, newly...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    Gloucester
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    About this property
    Relax and take in wonderful views of Gloucester's beautiful Good Harbor Beach, with Thatcher Island beyond, from this bright and delightfully furnished two bedroom vacation rental apartment. It is the perfect place to stay during your New England summer getaway! Both the living room and the...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Rockport
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Shared Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spend your days at the beach or relaxing poolside by your very own private pool. Rockport Hideaway is also only a short distance from Rockport's shopping, dining and family activities. Leave the car and stroll to the village, beaches, schools (with tennis courts and playground), and the commuter...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Gloucester
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Patio
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just 10 yards from the white sands and lively surf of Long Beach, this vacation rental condo sleeps 8 in central air conditioned comfort and offers 4 floors of living space with 3+ bedrooms and 2.5 baths. The aptly named Long Beach is one mile long and spans both Gloucester and Rockport. This...
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    Location Information
    Gloucester, Cape Ann 01930
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Salem
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    About this property
    My recently renovated spacious apartment can accommodate 8 people. It is close to all of the major attractions in Salem, including Salem's historical district, the Salem Witch museum, the waterfront, Salem State University, and Salem hospital. You will be a short (~5 minute) drive from the beach....
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    Salem, Massachusetts 01970
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    Gloucester
    5 Bedrooms, 2 Bathrooms, Sleeps 14 Quick View
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    • Washer
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    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Antique colonial offering a large place to spend time with family and friends. With lot's of place to sleep and chat. The location is perfect - just across from Stage Fort Park -- featuring a kids playground, Dog Park, Half-Moon Beach, Farmers Market, Sunday summer concert series, Gloucester Blue...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 14
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    Rockport
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Waterfront
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This waterfront historic vacation home is centrally located in the village of Rockport and was home to John Oakes in the late 18th and early 19th centuries. Completely renovated in 2015, it retains its old world charm. It has wonderful architectural details like an oversized (ornamental) fireplace,...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Gloucester
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    Perfect for 1 or 2 guests looking for an affordable summer get-away in beautiful location. The studio can also accommodate an infant in a pack-n-play or porta-crib, who is not yet walking. One block walk to Good Harbor Beach and scenic Back Shore. We call your home away from home, “Good Harbor...
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    Location Information
    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bathroom, Sleeps 2
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