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Pet Friendly Holiday Rentals in Chincoteague Island

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    Travellers to Chincoteague Island are booking April dates now. Secure your holiday rental today, and have the perfect trip.
    86 Matching Rentals in Chincoteague IslandView all 262 rentals
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    Jay's Retreat-Kayaker’s Delight use of 2 Kayaks; Nov Specials Start at $491 / 22
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Vacation House1 / 12
    (20)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Tranquil Shores - Relaxation With a Water View1 / 30
    (11)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Grill
    • Waterfront
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 July 2018
    Wow! Exceptionally close (walking distance) to both Assateague National Wildlife Refuge AND family friendly activities, such as bike shops and eateries. Very quiet...
    Reviewed 19 July 2018
    Communication with the owner was great. The house was in a convenient location near downtown on a very quiet street. The kids were able to ride their bikes there safely. We...
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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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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 12 June 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 31 August 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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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    Duck's Delight - Your Seaside Home Away From Home!1 / 19
    (46)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 5 May 2018
    This house is a 5 star! Great location people! Very neat, clean and cozy. Beds are comfortable, kitchen has everything you need to cook and a screen porch to relax. Price is...
    Reviewed 12 December 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
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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
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Windrush1 / 38
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 May 2018
    Looking for a secluded gem to get away for a few days? We were and this place fit the bill to a T! From the huge wrap-around deck, to the comfortable beds, the Windrush was the...
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    About this property
    Our guests come year after year to relax and enjoy truly fabulous views of our famous Chincoteague Bay sunset! This roomy, attractively decorated home is surrounded by water views, wetlands and birds! Windrush boasts lots of outdoor space including two screened porches, open decks/balconies and a...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Grill
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled beneath the tall pines is where you'll find this delightful Piney Island home. The Bird House features an open living room/kitchen/dining area, and extra 'family' space in the private den. The many large windows throughout the home create a bright, airy atmosphere. Enjoy relaxing breezes on...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Grey Heron is an amazing contemporary waterfront home nestled on the shoreline of Chincoteague Bay. You'll love the floor plan; a terrific great room with wood floors flanked by a kitchen on one side and a fireplace on the other. And great windows throughout! There's also a 'sitting room' with...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Cockleshell Cottage1 / 25
    (3)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Air Conditioning
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 June 2018
    This home by far was the best rental we have had yet. From the quiet peaceful area to the wildlife seen just from the backyard. Close enough to enjoy walking to the shops or...
    Reviewed 24 May 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...
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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 modern 3 bedroom, 3 bathroom home boasts a first-floor master bedroom suite (Queen), all amenities and comfortable furnishings. Upstairs...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Sunset Bay Villa 2031 / 26
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 September 2016
    My family and I were extremely satisfied with our stay at Sunset Bay Villa 203. The unit is tastefully decorated without being beach tacky.. The furniture is relatively new...
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    About this property
    Villa 203 is a new unit that has been professionally decorated and offers five-star luxury. Spacious and accommodating, the gourmet kitchen is perfect for cooking your favorite meals. It's well stocked and ready for your handiwork. There are three bedrooms, including a master bedroom suite with...
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    Chincoteague Island, Virginia 23336
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Balcony
    • Air Conditioning
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***6204 Poplar Street*** Island Cottage has a great in town location! Easy walk to historic downtown's shops and retaurants. Perfect for a budget frienldy vacation. Has Wi-Fi.*** This Property accepts Dogs 35lbs and Under Only.*** Bed Sizes: 1 Queen, 1 Double, 1 Twin.*** 2018 Off Season...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • DVD Player
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for a clean, comfortable spot that's conveniently located? It's here at Eastwinds! This 2 bedroom townhome features an open floor plan downstairs, and 2 bedrooms/2 full bathrooms upstairs. You're just a few minutes from downtown - restaurants, shopping, movie theater and more. And,...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Do you need a vacation rental where you can park your boat and bring your pet? You've found it! Sea Tag #23 is a great two bedroom unit (upper level) that overlooks beautiful Assateague Island. Enjoy relaxing on the covered porch after a day of fishing. The views of Assateague are fantastic and...
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    Chincoteague Island, Virginia 23336
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Egret's Walk1 / 9
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 July 2016
    This was a much needed vacation that our family of five looked forward to and will remember for years to come. The price was appropriate for the clean and quaint home. Staying...
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    About this property
    ***5368 Main Street*** Very enjoyable and immaculate traditional home will delight you stepping inside. Pet Friendly! Newly added Fenced in Back Yard and Wi-Fi. 1 bedroom and 1 bath downstairs/1 bedroom upstairs.*** This Property accepts Dogs 35lbs and Under Only.*** Bed Sizes: 1 Queen, 3...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Donovan's Reef1 / 15
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 August 2014
    Just returned from one of the best vacations ever. This house was nice and big. There were 8 in our party and there was plenty of room to speed out. The kitchen was well...
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    What a great house and it is PET FRIENDLY! Donovan's Reef is a classic home that offers large living spaces and bedrooms. On the first floor the original wood floors will guide you through a beautiful dining room (will seat 8 comfortably), right into a well appointed living room and den plus...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Bay Window1 / 16
    (4)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 August 2016
    We have stayed at the Bay Window several different years and enjoyed staying there. Since we have dogs, it is pet friendly and sits off the Main Street so we can walk our pets...
    Reviewed 26 September 2013
    First of all, BAY WINDOW is pet friendly. That was winning point #1 for our angel of a dog. House was clean & showed no evidence of previous dogs. Everything was easily...
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    About this property
    Clean, cool and affordable! Bay Window offers a nice, quiet location and bright, large rooms for your family! Located on a side street not far from South Main Street, you're conveniently located to the marina and East Side. Bay Window is pet friendly, so bring them along too! NOTE: 1 of the...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Bayside II1 / 20
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • DVD Player
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 September 2018
    Bayside II had everything you could ask for in a vacation home. Lots of amenities and the small things that make a house a home. Lots of room and open space with the living and...
    Reviewed 19 June 2018
    Our rental home was beautiful ! Well equipped! Clean! We couldn’t have asked for a more perfect place to rent. The process was simpleAnd we’re well tended to by the rental...
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    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Kate's Cottage1 / 11
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 September 2018
    We stayed at Kate's Cottage the last week in August with our daughter, her two boys and our 24 pound Sheltie. The place was absolutely perfect for us! There were two bedrooms...
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    About this property
    ***5348 Oak Drive-Piney Island*** Tucked away in Piney Island Just minutes from Assateague's nature trails and beach. Wireless internet and water access for canoe and kayak. Pet Friendly! New bedroom and bathroom added in 2013. All bedrooms on same level.*** Bed Sizes: 1 Queen, 1 Double, 2...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    East Wing1 / 11
    (2)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Terrace
    • Balcony
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 June 2018
    Absolutely amazing loved this place, cute comfortable family home. Minutes from everything. Would stay here again. Also recommend to anybody. You will be very pleased
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    About this property
    ***5159 Deep Hole Road*** This charming island cottage built in 1920 features wood plank floors, open-beam ceilings, a screened-in porch and a large yard. Llovingly restored, East Wing is within walking distance of Little Oyster Bay, a boat launch, playground, restaurants and the best ice cream...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    ***6301 Circle Drive*** Charming pet friendly cottage in serene island setting with easy access to the Beach and to the Old Town. Spacious yard and screened porch. 2 full bathrooms. Bedrooms include 1 large master BR with king-size; plus 1 BR with 2 twins; and a cozy den with sofa/sleeper. Pet...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Windshadow1 / 27
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 July 2018
    Great location, close to town. Beautiful view of the Chincoteague Bay. Lovely, well-organized home. Pet friendly, took our 2 dogs. We have stayed at several homes in...
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    About this property
    You will enjoy spectacular sunsets from this lovely waterfront home overlooking the Chincoteague Bay. There is a waterfront screened gazebo that leads to a dock great for crabbing/fishing. Inside is a large open floor plan with a brand new kitchen, living room with wood burning fireplace and dining...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Daisey Cottage1 / 15
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Air Conditioning
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    Reviewed 21 July 2018
    This cottage was adorable and had everything we needed. It made our beach vacation absolutely wonderful! The layout was open and the decor was adorable. The master bedroom...
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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: 4 pets max....
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    Tern Inn1 / 26
    (5)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 May 2018
    Nicely decorated and updated! Well equipped and clean! Can't beat the location! Beds are a little soft, but that's a personal preference! Will use whenever we come down!! Can...
    Reviewed 13 May 2018
    We loved Tern Inn before the change in ownership but the new owners have replaced all of the appliances and they are great!I hesitate to review the location, view, etc., because...
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    About this property
    Tastefully remodeled and comfortably furnished, TERN INN is a delightful 2 bedroom townhome you'll find nestled on the shoreline of the Assateague Channel. Open floor plan, master bedroom suite with balcony, private pier and unobstructed views of the Assateague Lighthouse are just a few of the many...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Nautica1 / 9
    (1)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Terrace
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 August 2015
    Rooms are a little small, but who needs room in them when all your going to do is sleep in them. Dressers to put your clothes in and closets to hang your clothes up. Not many...
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    About this property
    ***7503 Pony Cove Lane*** This pet friendly, affordble duplex is off the beaten path and has room for the whole family! With four bedrooms and two baths! And Wireless Internet.*** This Property accepts Dogs Only.*** Bed Sizes: 2 Queen, 4 Twin*** 2018 Off Season Rates: $600 weekly/$120 per...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Mermaid Crossing1 / 22
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    Smoking allowed
    Reviewed 11 July 2018
    This location was an unexpected delight! More than any one particular thing, it was comfortable! We will be returning!
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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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    About this property
    As a classic Chincoteague-style home, Hopkin's House is situated on the East Side of Chincoteague Island and overlooks the Assateague Channel. You'll enjoy a wonderful, relaxing vacation at this 3 bedroom home; it's just a short distance from the public boat ramp, Memorial Park, a restaurant and...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    A Shore Thing1 / 22
    (3)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 April 2016
    We had a great time at the vacation house. The house was as expected and nicely decorated. The beds were a little hard but the view was beautiful and made up for it. We...
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    About this property
    A very nice waterview duplex overlooking Assateague Island and the lighthouse. Located across the street from 'Mr. Baldy's Restaurant' and within walking distance to Memorial Park park (where there is a boat ramp, a fishing pier, and play area for the kids). Enjoy the waterside screened porch....
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 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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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 March 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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    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
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Pearl in the Pines1 / 10
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Reviewed 7 May 2017
    My family of 4 stayed here. We enjoyed the open floor plan, the large dining room table and that everything is on one level, the shower in master bedroom was not very spacious...
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    ****5476 Pearl Drive-Oyster Bay I*** Lovely home located in private community with water view and next to boat ramp. Wi-Fi Available. Nearby is DeColores in the Pines.*** Bed Sizes: 2 Queen, 2 Twin, 1 Queen Sleep Sofa*** Prime Season Rates: $1100 weekly/$220 nightly. Off Season Rates: $800...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sunset Bay Villa 2211 / 19
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    • Shared Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 July 2015
    Excellent and clean unit in a nice condo site. Close to the main area of town. Large unit with all the comforts of home. All household items we needed were there and in good...
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    About this property
    COME AND ENJOY! You've earned it. Located on the edge of beautiful Chincoteague Bay, Sunset Bay Villa 221 is a luxury waterfront condominium that sleeps 8 with three rooms for sleeping. This unit boasts over 1,700 square feet of luxury living space with all amenities - waterfront balcony, master...
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    Chincoteague Island, Virginia 23336
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***3584 Willow Street*** Pet Friendly. Charming restored island home will make you smile! Relax in the screened porch after a day at the beach. Close to everything! A Short walk to the carnival and historic downtown with shops and restarurants. Large yard, perfect for children and pets. Close...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    Captain's Loft1 / 22
    (4)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 October 2018
    Me and family really enjoyed our stay in this beautiful home in Chincoteague, very comfortable beds and rooms for a family of 8. the house is in a very quite location but near...
    Reviewed 15 September 2017
    Been coming to Chincoteague for years and have stayed all over the island. Hands down this is my favorite place. Clean, plenty of Bedrooms and Bathrooms. It also does have a...
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    About this property
    Captain's Loft has NEW OWNERS! This vacation home is located just a short walk to Maddox Blvd! Close to everything, but situated perfectly for a quiet and relaxing stay. This duplex home features three bedrooms downstairs, and two of those bedrooms have full baths. There's another full bath...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Tall Pines1 / 21
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • DVD Player
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 June 2017
    We stayed at Tall Pines on the advise of a friend. She said it was small, but nice.The house is all we needed as a family of four. The queen bedroom was bright and airy. The...
    Reviewed 29 August 2015
    Pros: Nestled in pine forest, well shaded so that AC was not necessary for most of our 2 week stay (esp when we could borrow fans from the management company). Very quiet...
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    About this property
    Located in lovely Piney Island within a short bike ride to the beach. This single story 2 bedroom, 1.5 bathroom house offers a large screened porch, fully equipped kitchen and spacious living room. Piney Island offers community water access great for launching kayaks/canoes. To top it all off, Tall...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    As one of our newest vacation rental offerings, we're pleased to be have this downtown charmer! Shreiner's Tradition is a renovated 2+ bedroom home located just outside the downtown area. Enjoy walking to restaurants, shopping, ice cream and the movie theater! This home features an eat-in kitchen,...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sunset Dreams II1 / 24
    (2)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 4 weeks ago
    House was sparkling clean! Fished, crabbed, and dug clams off the dock, very convenient. All the beds were very comfortable including the sofa bed. The stairs were easy to...
    Reviewed 24 June 2018
    The condo was on the main drag to the town. We faced the Bay, had the pier to fish & crab from any time we wished (my son & one grandson are avid fishermen), the location...
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    About this property
    This great waterfront townhouse on Chincoteague Bay features a waterside master bedroom suite with jetted tub, a waterside balcony for you to enjoy beautiful sunsets, a long pier for fishing & crabbing & much more. There's also a very nice screened porch! Other amenities include all appliances,...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sunset Bay Villa 1111 / 18
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 September 2016
    This place is really niiice!! Very spacious, modern kitchen.nice size bedrooms. Night time view off the living room/bedroom deck beautiful! It's very peaceful. I enjoyed...
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    About this property
    This 3 bedroom 2 bathroom luxury villa features a first floor, open floor plan villa for easy access, and it is dog friendly! The first bedroom offers a twin trundle bed, the second bedroom has a queen bed, and master suite has a queen bed with a private bathroom and access to the waterfront deck....
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    Location Information
    Chincoteague Island, Virginia 23336
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Grandview1 / 34
    (4)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 August 2017
    We had a wonderful & relaxing beach stay at Grandview. This house was great, right on the water. Such beautiful sunsets! We were concerned that the house was a bit further...
    Reviewed 18 August 2014
    We stayed at Grandview last week with two of our children, their spouses and four grandchildren. It was indeed a grand view from the house, deck and docks across the bay.When...
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    About this property
    Enjoy stunning sunsets from this 5 star home at water's edge. Relax with the amazing water view from the north side of the island. Every bedroom is a suite, to ensure all of the adults have the right amount of privacy and a quiet place to stow away with a book. The dining area is big enough to...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Cowboy Cottage1 / 18
    (4)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Wi-Fi
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 July 2018
    This was within walking distance of dollar general and some other shops, only a couple of miles from the beach!House was perfect!!!How was pet friendly and clean! lots of room...
    Reviewed 7 August 2017
    I found Chincoteague Island an enjoyable vacation destination. The Cowboy Cottage is a comforortable, somewhat rustic place to stay. It's central location on the island makes...
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    About this property
    Cowboy Cottage is a pet friendly home conveniently located a block from Maddox Blvd., and just a couple of blocks from downtown Main Street. This ranch-style home has an open floor plan and is handicap accessible with a ramp to enter the house and bedroom/bathroom accessibility. There is a large...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled on the edge of Assateague Bay and overlooking the wild salt marshes of Assateague and Morris Islands is where you'll find this gem. With capacity for 10 guests, the 4 bedroom 3 bath contemporary ranch home features a pier and dock on deep water, screened porch and open deck area, a widow's...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    A Summer Place1 / 18
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Terrace
    • Grill
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 October 2014
    The pics of the home make it appear very secluded. That is not the case. It is surrounded by 4 other homes with no direct access to the water. That being said - We had nice...
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    About this property
    ***5094 Blake Point Road**** Timeless Traditional home dates back to the turn of the century. Renovations have upgraded this fine 4 bedroom home that is also pet friendly and sleeps 10. Grand views of the Chincoteague Bay with large front screened porch and decks off both levels. Very quiet and...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Joint Venture1 / 23
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 June 2018
    We enjoyed a quiet, lovely view out of the back of the house. We were very comfortable in the house. The kitchen was simple, but stocked enough for our needs. The rooms are...
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    About this property
    Joint Venture is the perfect townhouse for an affordable vacation! Take a short stroll or bike ride to ice cream, mini golf or any of the shops on Maddox Blvd. Bike or drive to the beach from the property! Joint Venture offers a water view of Little Oyster Bay (tidal creek) that can be enjoyed any...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy one of the most amazing, unobstructed views of Assateague Bay and Island from the comfort of your own waterfront deck and balcony! Watch the ponies in the distance on the island, abundant waterfowl, or maybe even catch a glimpse of dolphins in the bay. Two kayaks are also provided if you...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Almost Heaven1 / 27
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 August 2018
    We have been to Chincoteague Island many times and have always stayed at various Chincoteague Resort vacation homes. Our favorite place was sold and we needed to find a new...
    Reviewed 12 August 2015
    This home offered everything we hoped for during an off season week. Hard to beat overlooking the bay & having our own dock. While the home wasn't updated, it was very...
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    About this property
    A lovely 3 bedroom waterfront Victorian home that features a first-floor bedroom with a queen bed and full bathroom with tub/shower. Almost Heaven is just that... boasting amazing sunsets over the Chincoteague Bay and a private pier great for crabbing and fishing! Almost Heaven is also Pet...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    SNUG HARBOR WATERFRONT COTTAGE with a stunning view of lighthouse and ponies!1 / 98
    (42)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Waterfront
    • Outdoor Dining Area
    • Grill
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 August 2018
    Adorable water front cottages nestled within a cozy neighborhood-- just driving minutes from Main Street, gift shops, restaurants, and the beach. Super laid back! Perfect for a...
    Reviewed 13 July 2018
    The staff are very polite and helpful. The cottages are clean and well maintained. And the view is stunning. It made my vacation very enjoyable!
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    About this property
    It's a celebration of nature in its most magnificent form, as the wild Chincoteague ponies run up and down the marshland, the local birds will sing you a song. As this perfect day comes to an end, the laid back reggae tunes will set the mood for the miraculous montage of Caribbean colors that make...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 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
    ***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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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 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
    Kid friendly
    Smoking allowed
    Reviewed 28 November 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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    ***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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Hill House1 / 18
    (2)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Wi-Fi
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 September 2013
    My family of five stayed with our in-laws with their family of six at this beautiful home in July of this year. Right on Main Street, within walking distance of a terrific...
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    About this property
    Welcome to the 'NEW' Hill House! Wonderful traditional island home with fantastic new upgrades! The kitchen has recently been renovated, along with the bathrooms. Excellent in town location, walk to dinner, movie, shopping & galleries. Hill House features 4 bedrooms and 2.5 bathrooms, with a first...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    Horseshoe Haven1 / 14
    (1)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 August 2018
    Cannot say enough about this wonderful rental & Harbour Realty. House was very clean & well stocked. A great family rental and a plus was being able to bring out pup...
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    ***7111 Horseshoe Lane*** Lovely home centrally located on a quiet residential street. Watch the Saltwater Cowboy's saddle up for the pony round ups right from the comfort of the airy screened porch. Too hot at the beach, no problem than enjoy the pool. This home has all the amenities for beach...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Kid friendly
    Smoking allowed
    About this property
    Tastefully remodeled and decorated, 'Gone Coastal' is the perfect motto for this beach getaway! Located close to downtown - movies, shopping, restaurants and more. And you're only about 2 miles to the entrance to the beach! This rental features all modern amenities (central a/c & all appliances)...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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