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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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    Vacation House1 / 12
    (20)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 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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    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 13 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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    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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    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
    Suitability
    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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    Windrush1 / 38
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    Suitability
    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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    Morning Memories1 / 21
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 August 2018
    We love staying in Lighthouse Estates and love Morning Memories! We enjoy bringing our dogs and like that it is pet friendly! We have everything we need there and the kitchen...
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    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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    On Island Time1 / 20
    (1)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 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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    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
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Mermaid Crossing1 / 22
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    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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    Island Sunrise1 / 28
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 September 2017
    Absolutely love Chincoteague and Island Sunrise. Such a pleasure dealing with ytour office. Love our trips and memoreis...til next year❤
    Reviewed 3 February 2014
    You should know that this is a duplex! We did not realize this and would not have been happy about it in peak season but the other half was empty so it was fine. I want to say...
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    About this property
    Island Sunrise is gorgeous 3 bedroom, 2.5 bathroom duplex home located in desirable Piney Island. Not only is this house pet friendly, but it offers a deep water boat dock and 3 spacious decks. The views of Assateague Island and the Assateague Channel truly are second to none! Additional amenities...
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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
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 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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    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, 1 Bathroom, Sleeps 6 Quick View
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    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    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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    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 20 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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    Cowboy Cottage1 / 18
    (4)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Wi-Fi
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 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 8 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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    Tuck Inn1 / 4
    (2)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Air Conditioning
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 August 2018
    Tuck Inn was great. It was our first time there. We have spent many summer weeks in Chincoteague and this place was the most "Chincoteaguey" of them all! Rustic and full...
    Reviewed 17 June 2016
    The house was nice but was older. It had the old beach house charm which we all loved. We had 3 kids with us (ages 3, 5, and 7). They all slept upstairs which was a little...
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    About this property
    ***6559 Church Street*** Island home with large back yard and deck and Internet. Pet Friendly! Nearby is Chincoteague Crossing. 2 bedrooms and 2 baths downstairs/2 bedrooms upstairs.*** Bed Sizes: 1 Queen, 1 Double, 4 Twin*** Prime Season Rates: $795 weekly/$159 per night. Off Season Rates:...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 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
    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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    • Air Conditioning
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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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    A 'Teague of Our Own1 / 21
    (3)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Wi-Fi
    • Air Conditioning
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 August 2018
    This pet-friendly home is a wonderfully comfortable place to spend a vacation. The owners have it furnished to satisfy many different tastes, - from those of us who like a...
    Reviewed 2 August 2018
    My family stayed here recently and had the best time! The house is comfortable and well-decorated, with great natural light, plenty of space to spread out, and lots of seating...
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    About this property
    Welcome to A 'Teague of Our Own! Formerly known as 'Stormbreak,' this in-town home is an easy walk or bike to downtown or Maddox Blvd. Nicely decorated with three bedrooms. Living room has abundant seating a flat screen TV and DVD player. Wireless internet service is provided. The enclosed porch...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
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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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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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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
    • Air Conditioning
    Suitability
    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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    Sunset Dreams II1 / 24
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • DVD Player
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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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    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Air Conditioning
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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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    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)
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    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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    Location Information
    Chincoteague Island, Virginia 23336
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Osprey1 / 20
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 May 2018
    Beautiful home great setup all you could ask for. Temperatures dropped and the winds were unbelievably cold during our stay. Pipes froze and we knew by the for sat that it...
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    About this property
    This great contemporary beach home is located at the edge of the community harbor area, a perfect location for you and your guests. As a pet friendly house, you'll enjoy the wide open spaces for your dogs. The home features an open floor plan with a lovely eat-in (and completely renovated!) kitchen...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 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 16 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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    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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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    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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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    ***5323 Hibiscus Drive-Oyster Bay I*** This spacious pet friendly home is located in the private community of Oyster Bay II. Enjoy your morning coffee from the large deck or screened porch. Wildlife abounds with deer, rabbits, ducks, geese, and lots of songbirds in this quiet retreat! Enjoy...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    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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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    East Wing1 / 11
    (2)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Reviewed 25 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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    ***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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    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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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    ***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
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Bayside1 / 26
    (6)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    Reviewed 2 weeks ago
    The townhouse was clean and spacious. The views were lovely and the location was convenient to everything. We enjoyed our stay.
    Reviewed 19 June 2018
    This was our second year at Bayside and we love it! It’s roomy enough for our whole family, 4 adults, 3 kids and our dog! The pier is amazing, we spent a lot of time out there...
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    About this property
    Luxury waterfront townhome overlooking Chincoteague Bay. Beautiful sunsets! Long pier for fishing and crabbing. All amenities including all appliances, central air and enclosed porch (with air conditioning). Need more room? Bayside already booked? Try our sister homes right next door, Sunset Dreams...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Great White1 / 23
    (5)Very good
    5 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Shared Outdoor Pool (Unheated)
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 March 2015
    We loved this rental property. Lots of room and places to hang out with friends and family. The deck was great in the evenings for a glass of wine :)Our kids really enjoyed...
    Reviewed 13 March 2015
    I have stayed in this house may times with my family and have had a wonderful time. Is spacious and have all the commodities needed for our group (we were nine). Very quiet and...
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    Huge 5 bedroom, 2.5 bath Victorian home right on Main Street - close to downtown. Great White is pet friendly & big enough to accomodate 12! Fantastic wrap-around screened porch out front! This home includes access to a swimming pool and fitness center at Sunset Bay Villas. Amenities include a...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 12
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    Donovan's Reef1 / 15
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Reviewed 12 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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    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    About this property
    Cute as a button! This cozy little cottage sleep 5, and it's conveniently located very close to Memorial Park and Pony Swim area. If you're looking for an affordable vacation, this is it! The modern amenities make for an enjoyable vacation - there's central air, washer/dryer and outside swing....
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 5
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    ***5421 Deep Hole Road -downstairs apt*** Secluded, quiet location with lots of yard for a pet. Pet Friendly!*** Bed Sizes: 1 Queen, 1 Double, 1 Sleep Sofa*** Prime Season Rates: $550 weekly/$110 nightly. Off Season Rates: $400 weekly/$80 nightly. Additional amenities include: dvd vcr/dvd,...
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    Location Information
    Chincoteague Island, Virginia 23336
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Kate's Cottage1 / 11
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed 7 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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    ***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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    Bay Window1 / 16
    (4)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Reviewed 16 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 27 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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    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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    Grandview1 / 34
    (4)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
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    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 19 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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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    About this property
    Your home away from home... enjoy the water views, bring your boat and use your own dock or just relax and listen to the whispering pines. Great views of Oyster Bay off the front deck. 3 Bedrooms, 2 full baths (plus another shower/bath downstairs), outside shower, washer and dryer, satellite TV,...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Bayside II1 / 20
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    Reviewed 2 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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    Nautica1 / 9
    (1)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    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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    ***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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    Heron Creek1 / 42
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 June 2018
    Fantastic time at Heron Creek. Couldn't ask for better. Very clean, very comfortable, perfectly situated.
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    About this property
    This beautiful creek front duplex has everything you could dream of in your vacation home. The moment you enter Heron Creek you'll be invited by the high foyer ceilings that will walk you into the spacious great room. There you'll find a beautiful upgraded kitchen with stainless appliances, granite...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    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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    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    About this property
    ***6582 Church Street*** Lovely spacious home with 2 enclosed sunporches. Large kitchen for those looking to cook. Nice back deck and 1st level bedrooms. 3rd bedroom is loft area. Close to town & shopping but very quiet and private setting. 2 bedrooms and 2 baths downstairs (includes master bed...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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