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Chincoteague Island Vacation Rentals

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    Travelers to Chincoteague Island are booking April dates now. Secure your vacation rental today, and have the perfect trip.
    All 277 Rentals in Chincoteague Island
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    Vacation House1 / 12
    (15)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    ' TEAGUERS DELIGHT ' Upscale Island Home with HOT1 / 16
    (4)Excellent
    2 Bedrooms, 4 Bathrooms, Sleeps 15 Quick View
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    Sea Adventure: Waterfront  Views, Pier at this Park Rental!!!1 / 19
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Sea Heart & Soul, Waterfront Memorial Park Rental1 / 32
    (9)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Waterfront
    • Ocean Views
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 19, 2017
    We had a wonderful stay and the location couldn't have been better for our family. My husband was able to get up early to fish at the pier and I was able to let the kids sleep...
    Reviewed July 10, 2017
    We had a wonderful time staying at the SHS. The owner was very friendly and acomodating. Our kids loved the playground right across the street! We cant wait to come back!
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    About this property
    SEA HEART&SOUL next to SEA ADVENTURE: This home offers open spaces, a cozy, clean and comfortable place to stay along with amazing adventures for everyone to explore. It is furnished with many necessities so you can rest, relax and enjoy, coolers, beach chairs, grill, beach toys, storage under...
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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beautiful Chincoteague Island retreat1 / 15
    (12)Very good
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Porch
    • DVD Player
    • Parking
    • Washer
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 23, 2017
    The house was a good location, very close to a lot of stores and attractions. Very cute layout, with a stocked kitchen, screened porch, and a lovely breakfast nook. The beds and...
    Reviewed September 22, 2017
    Enjoyed our stay here. Cozy and close to downtown. All appliances and A/C functioned well (except the vacuum cleaner -- never figured that one out). Screened porch was...
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    About this property
    Come stay and relax at this quiet retreat. This listing is a newly remodeled home which is tastefully decorated. There are three color themed bedroom's; which have two queens and two twin sized beds. There is serenity all around you, come sit on the screened in porch and relax while listening to...
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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Duck's Delight - Your Seaside Home Away From Home!1 / 19
    (45)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Grill
    • DVD Player
    • Wi-Fi
    • Patio
    • Parking
    • Porch
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 12, 2017
    We had a wonderful time at duck's delight. The house was great and the ducks even came to visit one morning. It was awesome!!! Thanks so much,The Frey's
    Reviewed September 12, 2017
    This is a truly well kept house with a great location for a terrific price. I will definitely try to rent it every time we go back to Chincoteague.
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    About this property
    Duck's Delight is our home in America's Happiest Seaside Town (2014 Coastal Living)! Entire home updated/renovated for the 2015 booking season! 4 bedroom (3 queen sized beds and 2 sets of bunkbeds), 2 bath Cape Cod in Chincoteague, VA., home of the Assateague ponies. Small fishing town on the...
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    Chincoteague Island, Virginia 23336
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Tranquil Shores - Relaxation With a Water View1 / 30
    (6)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Grill
    • Waterfront
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 5, 2017
    This home was just what we needed for the weekend. It was convenient to get to Main Street for the holiday happenings, stores, and restaurants, as well as convenient to the...
    Reviewed September 13, 2017
    This is a great house in a very good location (though the road is a bit rutted). The view from both decks is spectacular -- beautiful sunrises, even when there are some clouds...
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    About this property
    Peaceful 3 bedroom/2 bathroom home located directly on Eel Creek. Appreciate the natural beauty of Chincoteague Island with gorgeous nature views from both the lower level screened in porch as well as the balcony off of the master suite. Enjoy relaxing mornings with the sunrise and breeze filled...
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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Waterfront, 5 BR, 4 BA, Elevator, sleeps 101 / 48
    (1)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Patio
    • Grill
    • Washer
    • Waterfront
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 12, 2017
    Our family loved this home. It was spacious, comfortable, well appointed and oh that view. I ( the family chef) was very pleased with the state-of-the-art kitchen...I didn't...
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    About this property
    The Moorings North is an unique architecturally designed luxury 5 bedroom home in the heart of Chincoteague Island. The house is elegantly decorated and has mesmerizing panoramic views of Chincoteague Bay. It is conveniently located in walking distance to small shops, a coffee house, and...
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    Chincoteague Island, Virginia 23336
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Epiphany on Deep Hole Creek - Waterfront & Dock -wow!1 / 31
    (44)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Ocean Views
    • Patio
    • DVD Player
    • Wi-Fi
    • Waterfront
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 12, 2016
    My family and I thoroughly enjoyed our stay at the Epiphany house recently. The house is fully equipped with EVERYTHING you'll need to make your stay wonderful. We packed so...
    Reviewed August 31, 2015
    And what a week it was. The teens made the most of the clear, sunny days by swinging in the hammock, riding bikes, and kayaking and crabbing (for the first time). The parents...
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    About this property
    Epiphany on Deep Hole Creek. Deep Hole Creek Vacation Rentals Member, Chincoteague Chamber of Commerce Pets subject to approval and an additional fee. See DeepHoleCreek s ite for more info and photos.! Scroll down to email Blair & Martha (owners) . Or Call Blair & Martha at the number listed for...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    Lighthouse Pointe1 / 15
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Internet Access
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One of East Side's most popular rentals! Features include open floor plan with waterside balcony downstairs, and a spacious third level master bedroom suite with private waterside balcony. All levels have balconies or deck! Very conveniently located - close to Memorial Park, restaurants and marina....
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Eagle's View1 / 38
    (5)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Balcony
    • Internet Access
    • Terrace
    • DVD Player
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 4, 2017
    This beautiful home on the water was very relaxing. We stayed here over Memorial weekend and although it rained half of the time, we still were able to catch crabs two nights...
    Reviewed March 14, 2017
    Eagle’s View is a piece of paradise! My wife and I have been coming to Eagle’s View for many years, and each time is a renewing experience. The views from the house and...
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    About this property
    Eagle's View is a luxury vacation rental overlooking the Assateague Island Channel and lighthouse. Fully equipped for comfort and convenience, this house is your home base for quick access to beaches, Eastern Shore attractions, and natural beauty. In addition to basking on the unspoiled beaches,...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Air Conditioning
    • Grill
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    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bay Mist is a nice two bedroom town home that features water and lighthouse views. The first floor has a large dining/kitchen area, living room with TV and a half bath. Upstairs features a master suite bedroom (with newly remodeled bathroom) and a private balcony that offers lighthouse/water views,...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • DVD Player
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great 2 bedroom, 2.5 bath townhome in Lighthouse Estates community off East Side Drive. This home features all amenities including central air, washer/dryer and new kitchen appliances. In addition, there is a community pool as well as water access and a dock (shared) to fish and crab from. This is...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come enjoy this 2-bedroom, 2.5 bath townhouse in the Lighthouse Estates community off East Side Drive. There is a community pool as well as water access and a dock (shared) to fish and crab from. This unit features a washer/dryer, wireless internet, central air conditioning and all the other...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A light, bright and airy beach rental with community pool and water access with shared dock. The spacious 2 bedroom, 2.5 bathroom home is tastefully furnished and features all appliances including washer/dryer and dishwasher. Wireless internet is included. Come and enjoy a great stay! Additional...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***3189 Ridge Road****Lovely island home in great condition. Nice large back yard for the kids. Charcoal barbeque grill and close to Memorial Park and boat launch. 1 bedroom 1st floor/1 bedroom 2nd floor.***Bed Sizes: 1 Queen, 1 Bunk Bed (1 Twin & 1 Double Futon). 1 Double Futon***Prime Season...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Agape House1 / 15
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Air Conditioning
    • Grill
    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 3, 2016
    We have been vacationing on Chincoteague for years and Love everything about it, This is a great house with lots of room we had two adults and four teens and it worked out...
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    About this property
    A great three bedroom home with a convenient in town location - just a short distance to Maddox Blvd. and Main St. for dining, shopping, etc. The master suite has a queen bed and private bathroom with TV. The second bedroom offers two queen beds and lots of extra space. Through the open dining and...
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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***7460 Pony Swim Lane***Waterfront duplex with deep water dock and great views of Assateague Island and Lighthouse. Newly remodeled kitchen, living room, and dining room. Now offers wireless interenet. 2 bedrooms and 1 bath upstairs, 1 bath downstairs.*** Bed Sizes: 1 Queen, 4 Twin***Prime...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Southern Dream1 / 14
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 12, 2016
    My family has stayed at this rental for the last few summers when we go to Chincoteague. My favorite thing here is the view of the water from the deck. We love cooking out...
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    About this property
    Charming 3 bedroom ranch home located in one of Chincoteague Island's finer residential communities. Nice, quiet location with a water view of Oyster Bay. Spend your time outside on the spacious deck or screened porch - there's plenty of room for all! Many modern amenities such as central air, high...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    A Sea Change1 / 14
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
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    Smoking allowed
    Reviewed November 28, 2017
    We stayed a full week in this house and brought our dogs with us! An incredibly comfortable and updated home. The dogs enjoyed both their freedom to play in the fenced yard as...
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    About this property
    ***6166 Ocean Blvd***Pet Friendly with a fenced back yard, outside shower, Wi-Fi, Central A/C. All bedrooms and baths on the 1st floor. Sunny enclosed front porch. Beautiful renovated home close to everything! Nearby is Sunshine House & Atlantic Delight.***Bed Sizes: 1 King, 2 Twin, 1 Queen...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    ***3757 Willow Street***Completely renovated traditional home in town with bright cheerful rooms and offers all amenities. Pet friendly! Two bedrooms on second level of home and two walk thru third story bedrooms. Third story loft with 4 twin beds has a typical Traditional home steep staircase....
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    Chincoteague Island, Virginia 23336
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Cockleshell Cottage1 / 14
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    Reviewed May 24, 2017
    This home was decorated beautifully and was more than roomy for the two of us plus our 2 yorkies. Loved sitting on the back screened in porch while reading or eating ice cream...
    Reviewed July 26, 2015
    The rental was just perfect! We wished we could have stayed longer. The house was very clean, it was decorated so nice in a nautical theme. We were away from downtown...
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    About this property
    Nestled on a quiet cul-de-sac in a private community just off North Main Street (Oyster Bay II) is where you'll find the charming Cockleshell Cottage. This new 3 bedroom, 3 bathroom home boasts a first-floor master bedroom suite, all modern amenities and new furnishings. It is handlcap accessible....
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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***7134 Silver Sails Landing***Beautiful spacious duplex with all new furnishings. Screened porch overlooking the wetlands. Deck and community pool. Offers wireless internet!! Close to carnival grounds!***Bed Sizes: 2 Queen, 2 Twin.***Prime Season Rates: $1350 weekly/$270 per night.Off Season...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    Josie's Dream is a newer, more modern vacation rental that features a master bedroom suite with private bath and a great location across the street from Memorial Park. Walk to Etta's Restaurant, East Side Marina or Memorial Park. Note: parking has a two car maximum. Additional amenities include:...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    ***6201 Ocean Blvd***Bring your four legged friend to this well-appointed home within walking distance to restaurants, shops, and more! This is a great pet friendly house right in the heart of downtown. It offers DSL Wi-Fi and a fax machine in the separate sitting room off of the living room. The...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    This great 3BR/2.5BA home is located on Piney Island, our closest residential community to Assateague. Walk or bike to Assateague! Amenities include central air, large screened porch, open floor plan with nice kitchen and bedrooms on both levels. There's a fireplace for our fall guests. Spacious &...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    About this property
    Comfortable, pet friendly home on large, side-creek lot with fantastic views from both the front and back of house! Excellent crabbing from dock! (Property sits on creek only suitable for kayaks, canoes and crabbing.) Just a short distance to Memorial Park and Fairgrounds. 2 living room areas, 2...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    ***6153 Marsh Island Drive-Marsh Island*** The owners of this new vacation rental have taken special care to provide their guests with many extras, including 1 person kayaks, beach items and a crab pot for your use. The view looking across Chincoteague Channel to Reed Memorial Park is...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    Mallard's Walk1 / 25
    (1)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Reviewed August 14, 2016
    This is the second year we stayed at Mallard's Walk. We have stayed different places over the years, and this is by far our favorite. We love that the dock is across the road...
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    About this property
    Enjoy the wonderful bay breezes from this charming waterfront home. Three bedrooms, great spacious kitchen, quiet porch to relax on and your own private pier/dock on Assateague Channel. Watch our world famous Chincoteague wild ponies grazing in the salt marshes of Assateague Island. No smoking and...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful waterfront home with shared pier plus floating dock on deep water!! Ground level is a large screened patio perfect for those summer time seafood feasts. The first level is great room boasting reclaimed barn board walls and wide plank pine floors with a separate den and full bath. There is...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Key West Cottages1 / 4
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Balcony
    • Patio
    • Central Heating
    • Terrace
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 4, 2017
    This was an adorable little cottage with some fantastic amenities. The bed was really comfortable and the rain shower was nice. A full kitchen with coffee maker, dishes...
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    About this property
    Beautiful cottages located in the heart of Downtown Chincoteague with views of the Chincoteague Channel and Bay. The Key West Cottages are equipped with full kitchens, cozy living rooms, Queen bedrooms and large tiled showers. Amenities such as an indoor pool, hot tub and outdoor pool next door...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Sand Dollar1 / 14
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 12, 2017
    This house was really great. Spotlessly clean, appropriate beds for 4 adult couples. No bunk beds; yay! Nice long dining table that fit 8. Outfitted with cookware that did not...
    Reviewed February 13, 2017
    Husband,three children and spouses love Piney Island area.Perfect accomadations especially since hurricane on Sat. Kept us inside.Everything we needed.
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    About this property
    ***7142 Pine Drive-Piney Island***Lovely home in Piney Island offers views of Assateague Island and water access. Perfect for a large family. Community boat launch area great for kayakers. Within walking distance to Assateague and Water Park.***Also offering Internet connected Blu-Ray player***Bed...
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    Chincoteague Island, Virginia 23336
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Cozy cottage near Old town Fishing Village1 / 12
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 25, 2016
    Good:- Clean, comfortable and functional- Location walkable to Main St shops and a bowling alley- Window air conditioners worked wellCould be improved:- Owner's...
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    About this property
    Cute, colorful 2 bedroom cottage with front and back porches. Walking distance to charming old town Main Street shops and restaurants. Back yard with grill and picnic table. Outside shower. Have coffee on the sunny back porch overlooking private back yard. Lots of windows. Wifi. DVDs for...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Spacious, historic Chincoteague Is. vacation house1 / 13
    (10)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Reviewed August 7, 2017
    My family and I loved this house! It is such a well kept home and very cozy. Everything was clean and anything we needed for cooking and/or to keep the little ones entertained...
    Reviewed August 1, 2017
    The house was so comfortable, especially the front porch where we could relax and visit with old friends in the evenings. Beds were comfortable which is always a plus. Well...
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    About this property
    Totally updated but traditional 'home away from home' facing the Chincoteague Channel on Chincoteague Island, minutes from the quaint downtown and the Assateague National Seashore and Wildlife refuge. Relax in this spacious, clean, and beautifully furnished home with water views of the sunset from...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***5082 Twilley Drive***Contemporary 4 bedroom 3 bath Waterfront home. Pet friendly, located in a private area off North Main Street. Offers 2 master suites with waterfront balconies. This home does not disappoint with its vaulted ceilings and gas fireplace. Offers a well-equipped kitchen with...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    On Island Time1 / 20
    (1)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
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    Smoking allowed
    Reviewed March 29, 2017
    We have been coming to Chincoteague Island since 1988 and this is the best house we have been to. The décor is sweet and thoughtful. All the little touches are lovely and the...
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    About this property
    Wow... What a show piece! 'On Island Time' is exactly what you expect in your beach home, from the bright and fun decor to the spacious and bright floor plans, all of this wrapped in a traditional Eastern Shore Home. The front enclosed porch is great for reading or just relaxing in the afternoon...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    About this property
    Quaint and charming island cottage with all the amenities! Located on the southern end of the island, Daisey Cottage offers everything you'll need for an enjoyable vacation - central a/c, dishwasher, WiFi, washer/dryer and more. And it's even pet friendly! Additional amenities include: bedding 2:...
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    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    ***6206 Marsh Island Drive Unit #1***Wonderful effiencency condo unit located on Marsh Island. Enjoy some of the best water views and sunsets on Chincoteague. Fully equipped effiencincy kichen and laundry area. Shared pier and waterside picnic area. Comfortable and affordable with private...
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    Location Information
    Chincoteague Island, Virginia 23336
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Cedar Cove1 / 25
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 16, 2017
    Great home for our large family. Quiet location within a bike ride of everything Chincoteague has to offer. Would definitely book again.
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    About this property
    Beautiful custom waterfront home in Oyster Bay. The open floor plan is bright and airy with plenty of room for everyone. The downstairs features an open living & dining room w/ gas fireplace, kitchen, and the master bedroom and bathroom. Upstairs you'll find the other 2 bedrooms and bathroom, as...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Sunset Dreams is a Luxury Waterfront town-home overlooking Chincoteague Bay, the perfect spot for unwinding while you watch the island’s vivid sunsets. This unit includes a second-floor balcony, water views from almost every room, a large master suite, an enclosed air-conditioned porch, wireless...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    ***6368 Pine Drive-Piney Island***Brand new Piney Island home. Spacious design open and bright with large screened porch and two covered porches offer views of Assateague in the distance. Close to Edie's Folly. Acess to community boat dock.***This Property provides Linens & Towels.***Bed Sizes: 2...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Lighthouse Estates #31 / 22
    (2)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    • Shared Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 14, 2017
    The location was great, watching the lighthouse at night was amazing. The pool was wonderful to have and well cared for.
    Reviewed June 28, 2016
    Loved everything about this place! Location was perfect to Assateague Island and town. Our 13 year old twin grandchildren loved having big (queen-sizes) beds and own full...
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    About this property
    This comfortable, family friendly vacation rental is waiting for you to enjoy. This unit has pool access and dock access directly across the street for easy access for those fun family fishing and crabbing experiences. It is just a short distance to Memorial Park and Etta's Waterfront dining. The...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    ***4379 Ridge Road***Lovely 2 bedroom home conveniently located on Ridge Road, not far from Maddox Blvd, with many great island attractions. Perfect house for a family of 4! This house offers extra space in the large sunroom. Bright and airy, the sunroom works for both cool and warm weather. The...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bayside II is a well appointed, WATER VIEW, 3-bedroom duplex located just off of South Main Street on the quiet southern end of the island. This spacious, nearly 2,000 sq ft. home offers a family of up to 8 an open floor plan with plenty of space to enjoy. The home has 3 decks - 2 facing the...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come and enjoy this beautiful 3 bedroom villa! Conveniently located next to to pool, this ground-level condo allows you to walk right out from your balcony to the marina/dock. Enjoy all of the Chincoteague Island decor, spacious open floor plan, and the master bedroom suite featuring a private bath...
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    Location Information
    Chincoteague Island, Virginia 23336
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Paradise1 / 26
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 19, 2017
    Beautiful stunning and breath taking ! The view was beautiful. House was clean upon arrival, very spacious! Loved the kitchen. The bedrooms were very clean and spacious! Loved...
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    About this property
    If you're looking for that special vacation home that offers everything you'll need, look no further. Paradise offers all top-of-the-line amenities including cherry wood floors, chef's kitchen and spacious master bedroom suite with custom bathroom and Jacuzzi tub. The main floor features a bright,...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Abbie Thornton Cottage1 / 19
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Reviewed August 25, 2015
    My husband and I stayed at Abbie Thornton cottage in August 2015 and are SO happy we booked this place! It was absolutely wonderful, from the screened in porch (perfect spot...
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    About this property
    This charming Chincoteague cottage was built in the 1930's and is located directly across the street from the Chincoteague Bay. Abbie Thornton Cottage has kept much of the original integrity, but has been lovingly restored to offer all the modern comforts of home. There's a cozy screened porch off...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Snoozin' Goose1 / 14
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 29, 2017
    Well appointed, nicely decorated and comfortable in a neat neighborhood. Three bedrooms and multiple porches for breezy comfort with views of the bay and it's dog friendly...
    Reviewed April 19, 2014
    We liked the open floor plan, five decks (!), and location in the pines next to a canal leading to Oyster Bay. The home is in a very nice development in a quiet location, The...
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    About this property
    Beautiful 3 bedroom home located in one of Chincoteague Island's private WATERFRONT communities! Snoozin' Goose offers multiple outdoor porches, an open floor plan with large, bright rooms and modern amenities -- all in a quiet, peaceful location. Enjoy wonderful water views while sitting directly...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    NEW! Canalside 3BR Chincoteague Island Home w/Pier!1 / 26
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Grill
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    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 23, 2017
    What a wonderful house to spend the week. A great place to relax after watching rockets, exploring light houses, and combing the beach. Lots of crabs to come home to. Superb.
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    About this property
    Leave all of your worries behind when you stay at this marvelous 3-bedroom, 2-bathroom Chincoteague Island vacation rental house! Boasting space to sleep 8 guests, water views and a secluded canalside location with private pier, this quaint Virginia property will allow you to leave all your...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Bay Dreamer is a spacious 3 bedroom duplex home with multiple porches and decks and spectacular sunset views, just minutes from downtown. When you enter the home you'll find a furnished rec room. The second floor features an open living room (queen sleeper sofa), dining area and kitchen. There is a...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Additional Chincoteague Island Info

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    Island vacation rentals - seaside villas, waterfront homes and condos

    Browse through our vacation home rentals, and you’ll discover some very tempting choices for your family vacation. An historic Main Street home is surrounded by a private landscape with a screened porch, bikes and beach toys. A luxurious custom home overlooks beautiful Oyster Bay, and family-friendly condos feature waterside decks, swimming pool and marina.

    Abundant outdoor recreation and attractions

    Naturally, the seashore is the dominant focus for outdoor fun on Chincoteague Island. Fish from the dock or walk the beach. Take a bird-watching hike or bicycle ride through wildlife preserves and quaint island lanes. Enjoy dolphin watching, island tours and spectacular sunset views from your own guided cruise through remote bays and waterways. Either Assateague or Chincoteague beaches are ideal for family picnics and water sports.

    Believe it or not, the wild Chincoteague Ponies are an unusual attraction on adjacent Assateague Island. The kids will love a trip to the Chincoteague Pony Center to enjoy pony rides, a show and riding competition. Book a small, charter deep-sea fishing trip that offers the opportunity to land big game fish from mahi-mahi and tuna to marlin and sharks.

    Leisurely shopping and dining

    As a contrast to all of that outdoor adventure, explore the village feel of the historic downtown and Maddox Boulevard areas. You’ll find exceptional hand-crafted duck decoys and original wildlife and landscape paintings and charming gift shops. To keep you entertained on a lazy sun-filled afternoon, stop in at Sundial Books to browse for book favorites and enjoy a cup of coffee or tea.

    Fresh ocean fare dominates local restaurant menus that are loaded with clams, oysters, and all-you-can-eat seafood platters. Of course, you can’t take the kids on vacation without finding the perfect pizza place, and that would be Famous Pizza Family Restaurant. They’ve been serving home-fresh pizza, cheese steaks and more for over 30 years. And you positively have to stop in at The Sea Shell Café for a gourmet salad and authentic Smith Island Cakes. They even cater to your vacation home, if you want to skip the kitchen duties and enjoy their excellent dinner selections.

    Villa and home rentals – the perfect seashore vacation choice

    There is no better way to enjoy a lazy, leisurely island vacation than from your carefully-chosen home rental. You’ll have plenty of room to relax, waterside views to enjoy and some wonderful home-grilled meals or bountiful breakfasts that will long be memorable for your entire family.

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