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Holiday Rentals in Middletown

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    All 21 Rentals in Middletown
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    The following rentals are within 40 kilometres of Middletown.
    Gorgeous Home on Chester River1 / 16
    (2)Very good
    Chestertown, MD
    4 Bedrooms, 9 Bathrooms, Sleeps 8 Quick View
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    Waldins waterfront house with amazing views - Top of the Chesapeake1 / 25
    (1)Excellent
    Charlestown, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Belle Rose Cottage at Victory Farm (Pet Friendly!)1 / 17
    (2)Excellent
    Chestertown, MD
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Charming Apartment in Historic Chestertown, MD1 / 10
    (7)Excellent
    Chestertown, MD
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Terrace
    • Balcony
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 May 2017
    This is a lovely upstairs apartment with a super comfy bed, great shower, and everything you would want or need for an easy stay. The cupboards are stocked, you can cook if you...
    Reviewed 27 August 2015
    Absolutely the best deal for me in Chestertown. Came back to visit family and friends, and luckily this place was available. Home away from home, roomy, and I was able to work...
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    About this property
    This artistic, light-filled one-bedroom apartment is located in historic Chestertown, MD. The space includes kitchen/living room combo, bedroom with queen size bed, bathroom with shower and tub. An outdoor deck with cafe table and chairs is a nice place to sit on a sunny day. It is perfect for a...
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    Chestertown, Maryland 21620
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Retreat at a quiet, water front cottage1 / 14
    (3)Very good
    Chestertown, MD
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Air Conditioning
    • Grill
    • DVD Player
    • Washer
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 October 2014
    If the unit is under construction, do not rent it. We should have been notified of the construction and given the opportunity to cancel.
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    About this property
    Located close to both Chestertown (15 minutes) and Rock Hall (30 minutes), MD this quiet, simple but energetic space is an ideal gathering place for families and friends. Stay here and relax the entire visit or explore the many activities, restaurants and cultural venues available in the Kent...
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    Chestertown, Maryland 21620
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Cozy & Spacious Chestertown Home1 / 25
    (3)Excellent
    Chestertown, MD
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Parking
    • Private Garden
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 December 2017
    The home was very clean and comfortable. It was very convenient and well set up for 3 generations to stay during our visit to Washington College. Chestertown and Rock Hall...
    Reviewed 21 November 2017
    This property is beautifully appointed. Every amenity possible to make you feel at home. Pool is clean and well maintained. A PLUS!!
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    About this property
    Lovely home in a quiet setting very comfortably furnished all you need for a relaxing getaway. Located 7 miles from the center of Chestertown & 5 miles from the center of Rock Hall. This spacious rancher offers four bedrooms two of the four are master suite's, 3 bathrooms, wood burning fireplace &...
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    Chestertown, Maryland 21620
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Chester River House with Views1 / 11
    (3)Very good
    Chestertown, MD
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 September 2017
    The house had amazing views right on the river. It was also very comfortable and in a great location close to the little historic square. Would definitely stay here again and...
    Reviewed 15 August 2015
    The sunsets are magnificent. The house is comfy, but showing some deferred maintenance like grass growing from the gutters, green stuff on the exterior, landscaping so very...
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    About this property
    A 3 bedroom house on the Chester River with amazing sunsets over the dock. Fully equipped, with central air conditioning, dishwasher, washer, dryer and parking - also free use of kayaks to enjoy the Chester River. An ideal property for those dropping off, picking up, or just visiting a student at...
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    Chestertown, Maryland 21620
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    Wilmington
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wilmington Masterpiece ! The Hamilton is a beautifully renovated and decorated home by Redefined Luxury Homes. Luxury Rooms Cool Spring / Trolley Square + Complimentary Coffee/Bagels + Spa like rooms, crisp linens, bottled water, WIFI + Walking distance to Trolley Square, Public Transport,...
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    Wilmington, Delaware 19806
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Cozy Apartment in Chestertown1 / 7
    (1)Excellent
    Chestertown, MD
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 May 2017
    This first floor apartment is cozy, sweet, and convenient to everything downtown. A quick 2 block walk brings you to restaurants, shops, galleries, the Farmer's Market on...
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    About this property
    A delightful one-bedroom apartment located in historic Chestertown. Close to Washington College & Heron Point. Apartment accommodates 2 guests. It is the perfect place for enjoying this historic, artistic town on Maryland's Eastern Shore. The space includes kitchen/living room combo, bedroom with...
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    Chestertown, Maryland 21620
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Sunview Cottage on Chesapeake Bay1 / 22
    (1)Excellent
    Chestertown, MD
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Parking
    • Outdoor Dining Area
    • Private Garden
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 September 2015
    I took my mother here for a getaway birthday weekend. I wanted somewhere we could relax but also be inspired by our surroundings. This quaint cottage was perfect. Nestled close...
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    About this property
    Modern, Cozy 2-Bedroom Cottage with sleeping loft. Views of the Chesapeake Bay from house and wraparound deck. Perfect destination for a couples getaway, family trip or friends gathering to enjoy the Bay & Sunsets. Located in the scenic, serene environs of the Eastern Shore of Maryland in...
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    Chestertown, Maryland 21620
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Wilmington
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Balcony
    • Cable/satellite TV
    • Terrace
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wilmington Masterpiece ! The Hamilton is a beautifully renovated and decorated home by Redefined Luxury Homes. Located in the heart of Historic Wilmington Delaware and just steps away from Trolley Square, Museum District and close to the Downtown riverfront area. Excellent for large groups. no pets...
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    Wilmington, Delaware 19806
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    Chesapeake City, MD
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • Balcony
    • Terrace
    • Private Outdoor Pool (Unheated)
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This luxurious and recently built villa is ideally positioned, providing sumptuous, dazzling panoramic views over the Pinhal golf course, on the outskirts of Vilamoura. Boasting spacious living areas, the villa is equipped with a state of the art kitchen, as well as four elegant bedrooms all with...
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    Chesapeake City, Maryland 8125 422
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Charlestown, MD
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Private Garden
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waterfront living at its best. About 40 minutes from downtown Baltimore and 1.5 hours from DC. This is a quiet family oriented area, not a bustling tourist town. Bring your boat and put it in at the nearby ramp. Lovely bamboo floors in the living room. Fantastic views of the Chesapeake Bay. Kayak...
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    Charlestown, Maryland 21903
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Pennsville, NJ
    6 Bedrooms, 5 Bathrooms, Sleeps 19 Quick View
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    • Balcony
    • Cable/satellite TV
    • Patio
    • Grill
    • Washer
    • Housekeeping Included
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in rural Southern New Jersey, The Inn at M&M is unique, with a story dating to the 1600's. The Inn's scenic rural setting is ideal for your special occasion or private get-away. The Inn is equipped with modern bathrooms and all the amenities to make your stay enjoyable. This venue and...
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    Pennsville, New Jersey 08070
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 19
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    Still Pond, MD
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Wi-Fi
    • Patio
    • Private Garden
    • Washer
    • Parking
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious room w old pine floors, comes with semi-private bathroom, breakfast and some meals provided, in a charming Victorian in delightful town, half acre lot and shared use of rooms. Out and out close for 15 scenic launching areas for boating. Less than 5 mins to spectacular sunsets at Betterton....
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    Still Pond, Maryland 21667
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    New Castle
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Washer
    • Internet Access
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Explore the colonial roots of New Castle when you stay at this quaint 2-bedroom, 2-bathroom vacation rental house! Here, you'll find everything needed for a comfortable getaway including modern amenities like a open floor plan and fully equipped kitchen, with accommodations for 6 guests and...
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    New Castle, Delaware 19720
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Still Pond, MD
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Central Heating
    • Washer
    • Terrace
    • Patio
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious room w old pine floors, comes with semi-private bathroom, breakfast and some meals provided, in a charming Victorian in delightful town, half acre lot and shared use of rooms. Out and out close for 15 scenic launching areas for boating. Less than 5 mins to spectacular sunsets at Betterton....
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    Location Information
    Still Pond, Maryland 21667
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Wilmington
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Available Two bedrooms in 3 BDR HOME. Full size Rooms. sleep two. Fully equipped KITCHEN. FRONT Porch and Fenced In Back Yard for privacy. DIRCT TV! NON Smoking professionals preferred. Tenant Must be able to care for home, responsible for recycling, Must care of Property in bad weather, keep...
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    Wilmington, Delaware 19804
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Elkton, MD
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Washer
    • Housekeeping Included
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Children's Pool
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    I have a cozy cute 1 person bedroom and this cozy 2 person bedroom in beautiful wooded setting, close to Fair Hill nature preserve, in Elkton, MD 21921. with shared bathroom, shared kitchen, laundry corner, sun room, pesticide free gardens and eco conscious woods. Short term or long term. Everybody...
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    Elkton, Maryland 21921
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Elkton, MD
    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    • Secure Parking
    • Washer
    • Air Conditioning
    • Balcony
    • Grill
    • Cable/satellite TV
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    I have 2 double bed rooms and a 1 person bedroom with shared bathroom, kitchen, sun room, deck, woods with bonfire, cob oven, yurt, outdoor bathroom, free roaming chickens, sheep, goat, cats, dogs, people, plants, gardens, fish pond, playground, bikes available, close to Fair Hill nature preserve,...
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    Elkton, Maryland 21921
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 1
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    Hockessin
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    * Please note that other renters live on site, in completely separate units, and may be present during your stay * Take a trip to the edge of Delaware and stay at this studio vacation rental apartment that sleeps 2 in Hockessin! You'll have the best of the northeast at your fingertips - with...
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    Hockessin, Delaware 19707
    Condo/Apartment - 1 Bathroom, Sleeps 2
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