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Holiday Rentals in Chincoteague Island

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    ₹ 10,309 Average
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    ₹ 0₹ 63,000+
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    Travellers to Chincoteague Island are booking April dates now. Secure your holiday home today, and have the perfect trip.
    All 268 Rentals in Chincoteague Island
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    Vacation House1 / 12
    (15)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Spacious, historic Chincoteague Is. vacation house1 / 13
    (10)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Sea Heart & Soul, Waterfront Memorial Park Rental1 / 32
    (9)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Waterman's Cottage1 / 21
    (40)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Secure Parking
    • Porch
    • Grill
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 September 2017
    The cottage was cute, but not so clean. The washer overflowed, but the property manager was on it and got a repair person out right away. The kitchen is not stocked well with...
    Reviewed 7 September 2017
    Great island feel. We had an issue with the air conditioning and it was fixed very quickly. Great location with easy walk to wonderful little shops and beautiful water views
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    About this property
    This historic Waterman's Cottage , circa 1920, located on Chincoteague Island, has been beautifully restored and is a perfect family vacation spot. We are across the street from the Chincoteague Bay and 1 mile to the center of town. The house has a large eat-in-kitchen, family room as well as a...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sea Adventure: Waterfront  Views, Pier at this Park Rental!!!1 / 19
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Ocean Views
    • DVD Player
    • Washer
    • Air Conditioning
    • Waterfront
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 July 2016
    We had rented both houses SHS and SA for our family/friends with kids. The house was very clean and comfortable for all. Very kid friendly, since it was just across from the...
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    About this property
    SEA ADVENTURE next to Sea Heart and Soul are 2 miles from Assateague Island and 5 miles from beach front fun. Check-in 4pm/ check-out 12pm. $229.00 per night. This home, right out your front door, has the coolest waterfront park ever!!! Chincoteague Veteran's Memorial Park, for the recreation of...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beautiful Chincoteague Island retreat1 / 15
    (12)Very good
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Porch
    • DVD Player
    • Parking
    • Washer
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 September 2017
    The house was a good location, very close to a lot of stores and attractions. Very cute layout, with a stocked kitchen, screened porch, and a lovely breakfast nook. The beds and...
    Reviewed 22 September 2017
    Enjoyed our stay here. Cozy and close to downtown. All appliances and A/C functioned well (except the vacuum cleaner -- never figured that one out). Screened porch was...
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    About this property
    Come stay and relax at this quiet retreat. This listing is a newly remodeled home which is tastefully decorated. There are three color themed bedroom's; which have two queens and two twin sized beds. There is serenity all around you, come sit on the screened in porch and relax while listening to...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    NEW! Canalside 3BR Chincoteague Island Home w/Pier!1 / 26
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Grill
    • Cable/satellite TV
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 November 2017
    What a wonderful house to spend the week. A great place to relax after watching rockets, exploring light houses, and combing the beach. Lots of crabs to come home to. Superb.
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    About this property
    Leave all of your worries behind when you stay at this marvelous 3-bedroom, 2-bathroom Chincoteague Island vacation rental house! Boasting space to sleep 8 guests, water views and a secluded canalside location with private pier, this quaint Virginia property will allow you to leave all your...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Tranquil Shores - Relaxation With a Water View1 / 30
    (6)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Grill
    • Waterfront
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 December 2017
    This home was just what we needed for the weekend. It was convenient to get to Main Street for the holiday happenings, stores, and restaurants, as well as convenient to the...
    Reviewed 14 September 2017
    This is a great house in a very good location (though the road is a bit rutted). The view from both decks is spectacular -- beautiful sunrises, even when there are some clouds...
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    About this property
    Peaceful 3 bedroom/2 bathroom home located directly on Eel Creek. Appreciate the natural beauty of Chincoteague Island with gorgeous nature views from both the lower level screened in porch as well as the balcony off of the master suite. Enjoy relaxing mornings with the sunrise and breeze filled...
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    Location Information
    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
    (45)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Grill
    • DVD Player
    • Wi-Fi
    • Patio
    • Parking
    • Porch
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 weeks ago
    We had a wonderful time at duck's delight. The house was great and the ducks even came to visit one morning. It was awesome!!! Thanks so much,The Frey's
    Reviewed 12 September 2017
    This is a truly well kept house with a great location for a terrific price. I will definitely try to rent it every time we go back to Chincoteague.
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    About this property
    Duck's Delight is our home in America's Happiest Seaside Town (2014 Coastal Living)! Entire home updated/renovated for the 2015 booking season! 4 bedroom (3 queen sized beds and 2 sets of bunkbeds), 2 bath Cape Cod in Chincoteague, VA., home of the Assateague ponies. Small fishing town on the...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Epiphany on Deep Hole Creek - Waterfront & Dock -wow!1 / 31
    (44)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Ocean Views
    • Patio
    • DVD Player
    • Wi-Fi
    • Waterfront
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 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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    Waterfront, 5 BR, 4 BA, Elevator, sleeps 101 / 48
    (1)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Patio
    • Grill
    • Washer
    • Waterfront
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 June 2017
    Our family loved this home. It was spacious, comfortable, well appointed and oh that view. I ( the family chef) was very pleased with the state-of-the-art kitchen...I didn't...
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    About this property
    The Moorings North is an unique architecturally designed luxury 5 bedroom home in the heart of Chincoteague Island. The house is elegantly decorated and has mesmerizing panoramic views of Chincoteague Bay. It is conveniently located in walking distance to small shops, a coffee house, and...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Ocean View Retreat1 / 25
    (4)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • DVD Player
    • Air Conditioning
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 September 2015
    We rented this house because our favorite house with another Chincoeague rental agency was not available. While this house is nice, we prefer the other one. The view here is...
    Reviewed 14 August 2015
    This was our second year at this house. The house is beautiful. The kids STILL love 'THE CAPTAINS QUARTERS'.... Crabbing of the dock was so much fun. The morning view off the...
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    About this property
    Nestled on the eastern tip of Chincoteague Island, this spacious waterfront estate has been designed and meticulously constructed by a local craftsman. Enjoy the unobstructed views of Assateague Channel and the lighthouse while the sounds of nature delight your senses. Features include 5 bedrooms,...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    Cozy cottage near Old town Fishing Village1 / 12
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Private Garden
    • Washer
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 August 2016
    Good:- Clean, comfortable and functional- Location walkable to Main St shops and a bowling alley- Window air conditioners worked wellCould be improved:- Owner's...
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    About this property
    Cute, colorful 2 bedroom cottage with front and back porches. Walking distance to charming old town Main Street shops and restaurants. Back yard with grill and picnic table. Outside shower. Have coffee on the sunny back porch overlooking private back yard. Lots of windows. Wifi. DVDs for...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Whispering Pines1 / 24
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Cable/satellite TV
    • DVD Player
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 August 2017
    Great location...close to harbor for flounder fishing! Enjoyed the bikes at the house. We visit Chincoteague on a regular basis. Just love the island!
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    About this property
    Whispering Pines is a clean and comfortable duplex home located at the south end of the island next to the old Beebe Ranch of Misty fame. The property was once part of the Beebe Ranch so Misty probably grazed there! Whispering Pines accommodates up to 8 guests, utilizing the sleep sofa in the...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Internet Access
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located very close to town, Bay Breeze will remind you of summer vacations as a child. This 3 bedroom, 2 bath homes sleeps 6 and has a washer & dryer, window a/c, and a ton of charm! Comfortable and affordable - this may be your spot at the beach! Additional amenities include: laundry: washer &...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Key West Cottages1 / 4
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Balcony
    • Patio
    • Central Heating
    • Terrace
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 October 2017
    This was an adorable little cottage with some fantastic amenities. The bed was really comfortable and the rain shower was nice. A full kitchen with coffee maker, dishes...
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    About this property
    Beautiful cottages located in the heart of Downtown Chincoteague with views of the Chincoteague Channel and Bay. The Key West Cottages are equipped with full kitchens, cozy living rooms, Queen bedrooms and large tiled showers. Amenities such as an indoor pool, hot tub and outdoor pool next door...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Grill
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A destination unto itself, Sea Oats offers wide open spaces, beautiful waterfront and views of Oyster Bay and plenty of room to spread out and relax. A luxury vacation rental home with all the bells and whistles, Sea Oats will delight your senses. From the tastefully decorated rooms and...
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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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    • 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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    • Internet Access
    • Air Conditioning
    • DVD Player
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    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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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Luxury waterfront home in Salt Marsh Landing. Spectacular sunsets. A long, private pier over the salt marsh leads you to a bay front dock area with shade. It's perfect for crabbing, fishing or canoe and kayak launching. Well appointed and architecturally pleasing, Castlebar features a main level...
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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 10 Quick View
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    • DVD Player
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Agape House1 / 15
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Air Conditioning
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 June 2016
    We have been vacationing on Chincoteague for years and Love everything about it, This is a great house with lots of room we had two adults and four teens and it worked out...
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    About this property
    A great three bedroom home with a convenient in town location - just a short distance to Maddox Blvd. and Main St. for dining, shopping, etc. The master suite has a queen bed and private bathroom with TV. The second bedroom offers two queen beds and lots of extra space. Through the open dining and...
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    Chincoteague Island, Virginia 23336
    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
    • Grill
    • DVD Player
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***5215 Shell Drive***'Belle of The Bay' is a unique vacation experience. Premier & private location for total waterfront enjoyment on Chincoteague's Oyster Bay and overlooking Assateague Island. Panoramic views, large multi-level decks & screened porch. 3 bedroom home sleeps 8 and bonus area...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Lighthouse Estates #31 / 22
    (2)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Air Conditioning
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 September 2017
    The location was great, watching the lighthouse at night was amazing. The pool was wonderful to have and well cared for.
    Reviewed 28 June 2016
    Loved everything about this place! Location was perfect to Assateague Island and town. Our 13 year old twin grandchildren loved having big (queen-sizes) beds and own full...
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    About this property
    This comfortable, family friendly vacation rental is waiting for you to enjoy. This unit has pool access and dock access directly across the street for easy access for those fun family fishing and crabbing experiences. It is just a short distance to Memorial Park and Etta's Waterfront dining. The...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Grill
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Anchor’s Rest—Centrally located, just a short walk to the carnival grounds, shopping, ice cream, dinner and the movies. This welcoming, spacious rental home features a fully equipped kitchen (don’t forget to bring k-cups!) with abundant counter space opening into the separate dining room. Enjoy the...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Lighthouse View Townhouse1 / 15
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • DVD Player
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 July 2016
    I enjoyed my stay in this home. My only complaint is that I initially inquired if there was a dishwasher prior to renting because it was not listed as an amenity. I was answered...
    Reviewed 8 April 2015
    We have stayed in this rental several times over the past 14 years. It is well furnished, has plenty of room, is beautifully decorated, and excellent for a large family!! The...
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    About this property
    Lighthouse View is located on the east side of our ialnd and includes a private community pool for your enjoyment. The 3 bedroom, 2 bath townhouse features two first floor bedrooms with full bath in the hallway and a master bedroom suite upstairs. There's water access across the street with a...
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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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    • Washer
    • Air Conditioning
    • Housekeeping Included
    • Ocean Views
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    SEA HARBOR: 1 mile from Assateague Island and 5 miles from beach front fun. Check-In 4pm Check-Out 12pm. This home offers large open spaces, a cozy, clean and comfortable place to stay along with amazing adventures for everyone to explore. It is furnished with many necessities so you can rest,...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Island Estate1 / 18
    (2)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Internet Access
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 July 2015
    Island Estate is probably one of Chincoteague's best kept secret! We came with our children, their wives, and children. We had 5 children, all 5 and under. The house was large...
    Reviewed 7 July 2014
    Absolutely gorgeous home. Rooms are much bigger than they look in photos! Private dock is great for crabbing and kayaking! Pool was very refreshing and a huge plus! Plenty...
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    About this property
    Fabulous, fabulous, fabulous! If you're looking for a large space to have a family vacation or reunion, this is it. This beautiful waterfront home is located on a tidal creek and boasts over 3,000 sq ft of living space. All amenities - central air, all kitchen appliances and more. The formal dining...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Air Conditioning
    • DVD Player
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    Pet friendly
    Kid friendly
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    About this property
    Beautiful 3 Bedroom, 2 bath single family home located in Piney Island - the closest community to the beach! Downstairs you'll find an open kitchen and dining area, living room, 2 bedrooms (with twin beds), a bathroom, and a large screen porch. Perfect for enjoying meals outside in the breeze! The...
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    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, 3 Bathrooms, Sleeps 12 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 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 12 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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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Terrace
    • Balcony
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***6321 Captain's Lane Unit #320 Sunset Bay Villas***Luxury Waterfront Condo will delight you with it's vast waterfront views and stylish décor. Overlooking the channel and also offering expansive views of the quaint town of Chincoteague Island. Lovely 3rd floor unit with waterviews from every...
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    Chincoteague Island, Virginia 23336
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tall Pines1 / 8
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
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    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, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This property has a location that is rich with amenities. Situated right next to Memorial Park, you can sit on the deck and enjoy the water views as the kids run, play, skateboard, fish and crab. The first floor is an open room consisting of the kitchen, dining area and living room (with queen...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    About this property
    Avalon is an exquisite 4 bedroom, 2.5 bathroom home situated on a bulkheaded lot on Oyster Bay! There is a large great room that boasts to family rooms, a dining area and large kitchen. Starting from the gas fireplace to the 16' cathedral knotted pine ceilings this home is bright, warm and...
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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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    • DVD Player
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    Pet friendly
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    About this property
    ***6201 Ocean Blvd***Bring your four legged friend to this well-appointed home within walking distance to restaurants, shops, and more! This is a great pet friendly house right in the heart of downtown. It offers DSL Wi-Fi and a fax machine in the separate sitting room off of the living room. The...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Blue Heron1 / 19
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 July 2017
    Stayed at the Blue Heron rental property in Chincoteague, Va. An excellent property for two families or four couples. Excellent location, not far from the beach. This...
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    About this property
    This modern beach retreat features an open floor plan, perfect for socializing with friends or just relaxing after a fun day at the beach. It is located on Oak Drive on Piney Island, closest neighborhood to the beach and convenient for shopping and dining on Maddox Blvd. A few of the amenities...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Lavinder House1 / 35
    (1)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
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    Pet friendly
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    Reviewed 16 November 2017
    This gerrymandered Victorian is the almost perfect weekend get-a-way rental - except . . . Of the five bedrooms, there is only one that you can get to without climbing steep and...
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    About this property
    Tucked away off North Main on the waterfront, Lavinder House is a charming Victorian-style home steeped in tradition. From the original woodwork to the brick kitchen floor, you'll enjoy the original integrity this island home features. Once the home of actress Linda Lavin, Lavinder House tells its...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Island Sunrise1 / 13
    (2)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    Pet friendly
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    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, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***3402 Ridge Road***Lovely 2 Bedrooms, 1.5 Baths duplex with water views. This duplex overlooks Assateague Island with great views for the Pony Swim. This is the Best way to watch the Pony Swim and not move from your porch! Sit and enjoy the views from 2 porches. The screened porch is off of the...
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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, 3 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Blue Sea Star! You'll fall in love with this fabulous 3 bedroom, new construction home from the moment you walk in the door. Bright open spaces, lots of windows, wood floors, first floor master bedroom/bathroom, and too much more to name! Located on a quiet cul-de-sac in Oyster Bay II...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    Red Cedar1 / 16
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    Reviewed 11 June 2017
    Comfortable 3 bedroom house surrounded by nature. At various points we saw herds of goats, llama, or ponies, raccoons, opossum, a variety of birds, and at night the chatter of...
    Reviewed 30 September 2016
    My wife and I stayed here in early September, 2016 for four nights to go kayaking and explore the area. The house worked very well for us. The beauty of the Red Cedar is the...
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    About this property
    Nature calls at this nicely appointed 3 bedroom rental home! Red Cedar is nestled on the edge of a huge expanse of nature preserve-type land where you'll see all types of native wildlife. Birders bring your life list. The home features modern amenities, offers a first floor bedroom, full laundry,...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Island Girl1 / 19
    (5)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 October 2017
    First of all Island Girl has an Island vibe. The house is very bright and airy and it gets a lot of natural light. We enjoyed the deck and the screened in porch. It was misty...
    Reviewed 17 September 2015
    This was the perfect rental for our party. We had three couples and 4 kids. There are three beds, all queen, and the loft has four twins. The kids loved being in the loft...
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    About this property
    Spacious waterfront home with water views from every window! The Great Room includes comfortable living and dining areas and a modern, fully stocked kitchen w/ breakfast bar. Amenities include central heat & air, private outside shower, wood stove, grill, screened porch and lots of deck space! And...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 11
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    An Unfettered View1 / 25
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 May 2017
    We try to visit the Eastern Shore near Assateague once a year in May before the summer crowds come in. We'd usually tent camp at Assateague seashore or Toms Cove but this year...
    Reviewed 13 September 2016
    This place is absolutely EVERYTHING you could hope for on vacation. The home is immaculately clean and lots of room. The well-kept , private dock is an exciting and successful...
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    About this property
    This beautiful 2BR ranch home has a quiet, out-of-the-way location on little Oyster Bay. The views of the bay are beautiful and expansive with a long pier straight from the back deck its perfect for crabbing, kayaking & canoeing. An Unfettered View features all amenities including a private master...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    This beautifully renovated 4 bedroom, 2 bathroom home could be the ideal vacation home for your family and/or friends. Located on Oak Dr in Piney Island this home is an easy bike riding distance to the beach and trails of Assateague Island. Aramabad has a completely renovated kitchen with granite...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    Josie's Dream is a newer, more modern vacation rental that features a master bedroom suite with private bath and a great location across the street from Memorial Park. Walk to Etta's Restaurant, East Side Marina or Memorial Park. Note: parking has a two car maximum. Additional amenities include:...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Southern Dream1 / 14
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 March 2016
    My family has stayed at this rental for the last few summers when we go to Chincoteague. My favorite thing here is the view of the water from the deck. We love cooking out...
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    About this property
    Charming 3 bedroom ranch home located in one of Chincoteague Island's finer residential communities. Nice, quiet location with a water view of Oyster Bay. Spend your time outside on the spacious deck or screened porch - there's plenty of room for all! Many modern amenities such as central air, high...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    About this property
    This delightful townhome features beach living at it's best. The Master Bedroom offers a private balcony with sunset views. Snow goose also offers (shared) dock access to a tidal canal that is full of wildlife. Additional amenities include: sight seeing, view: water access, laundry: washer &...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Donovan's Reef1 / 15
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Pet friendly
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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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    Shady Side1 / 21
    (4)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Reviewed 18 July 2017
    This house was perfect for us. It is well maintained and not a lot of insects on this part of the island. The light of the lighthouse was a great bonus and the screened in...
    Reviewed 17 May 2017
    We stayed at this property last year and are excited to be heading back soon. The house is the closest road to the beach on the island! You are able to take a morning walk...
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    About this property
    Shady Side is located in Piney Island, which is among the closest communities to the beach. There is community water access, suitable for a kayak or canoe. The house features two queen bedrooms and a full bath downstairs. Upstairs you'll find two additional bedrooms, one has two twins and the...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful waterfront home with shared pier plus floating dock on deep water!! Ground level is a large screened patio perfect for those summer time seafood feasts. The first level is great room boasting reclaimed barn board walls and wide plank pine floors with a separate den and full bath. There is...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    1
    Island holiday rentals - seaside villas, waterfront homes and condos

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

    Abundant outdoor recreation and attractions

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

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

    Leisurely shopping and dining

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

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

    Villa and home rentals – the perfect seashore holiday choice

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

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