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Chincoteague Island Holiday Rentals

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    Travellers to Chincoteague Island are booking April dates now. Secure your holiday rental today, and have the perfect trip.
    All 277 Rentals in Chincoteague Island
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    ' TEAGUERS DELIGHT ' Upscale Island Home with HOT1 / 16
    (4)Excellent
    2 Bedrooms, 4 Bathrooms, Sleeps 15 Quick View
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    Sea Adventure: Waterfront  Views, Pier at this Park Rental!!!1 / 19
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Sea Heart & Soul, Waterfront Memorial Park Rental1 / 32
    (9)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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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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    Pet friendly
    Kid friendly
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    Reviewed 7 August 2017
    My family and I loved this house! It is such a well kept home and very cozy. Everything was clean and anything we needed for cooking and/or to keep the little ones entertained...
    Reviewed 1 August 2017
    The house was so comfortable, especially the front porch where we could relax and visit with old friends in the evenings. Beds were comfortable which is always a plus. Well...
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    About this property
    Totally updated but traditional 'home away from home' facing the Chincoteague Channel on Chincoteague Island, minutes from the quaint downtown and the Assateague National Seashore and Wildlife refuge. Relax in this spacious, clean, and beautifully furnished home with water views of the sunset from...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Vacation House1 / 12
    (15)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Porch
    • Balcony
    • Grill
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 September 2017
    Very happy with the property. It was clean, roomy and plenty of modern appliances. We found the place to be very quiet and relaxing. Close enough to all the major attractions...
    Reviewed 22 September 2017
    Enjoyed our stay overall. House is almost new and was well stocked with essentials. Fast internet and nice tv and stereo. Owner was made aware that there were some cleaning...
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    About this property
    5203 Wild Pony Court. Oyster Bay II community. 2 story house located on secluded cul-de-sac. 3 bedrooms, 2 1/2 bathrooms, kitchen, laundry, living, and dining rooms, screened porch, wrap around porch, handicapped ramp, master bedroom on main floor. Private back yard and parking. Located on the...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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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    Eagle's View1 / 38
    (5)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Patio
    • Balcony
    • Internet Access
    • Terrace
    • DVD Player
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 June 2017
    This beautiful home on the water was very relaxing. We stayed here over Memorial weekend and although it rained half of the time, we still were able to catch crabs two nights...
    Reviewed 14 March 2017
    Eagle’s View is a piece of paradise! My wife and I have been coming to Eagle’s View for many years, and each time is a renewing experience. The views from the house and...
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    About this property
    Eagle's View is a luxury vacation rental overlooking the Assateague Island Channel and lighthouse. Fully equipped for comfort and convenience, this house is your home base for quick access to beaches, Eastern Shore attractions, and natural beauty. In addition to basking on the unspoiled beaches,...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 4 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 13 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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    Key West Cottages1 / 4
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Balcony
    • Patio
    • Central Heating
    • Terrace
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 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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    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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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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 23 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 trailer-style property will allow you to leave all your...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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 12 December 2017
    We had a wonderful time at duck's delight. The house was great and the ducks even came to visit one morning. It was awesome!!! Thanks so much,The Frey's
    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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    Location Information
    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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    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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    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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    Cedar Cove1 / 25
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • DVD Player
    • Waterfront
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 September 2017
    Great home for our large family. Quiet location within a bike ride of everything Chincoteague has to offer. Would definitely book again.
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    About this property
    Beautiful custom waterfront home in Oyster Bay. The open floor plan is bright and airy with plenty of room for everyone. The downstairs features an open living & dining room w/ gas fireplace, kitchen, and the master bedroom and bathroom. Upstairs you'll find the other 2 bedrooms and bathroom, as...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Air Conditioning
    • Grill
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bay Mist is a nice two bedroom town home that features water and lighthouse views. The first floor has a large dining/kitchen area, living room with TV and a half bath. Upstairs features a master suite bedroom (with newly remodeled bathroom) and a private balcony that offers lighthouse/water views,...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come enjoy this 2-bedroom, 2.5 bath townhouse in the Lighthouse Estates community off East Side Drive. There is a community pool as well as water access and a dock (shared) to fish and crab from. This unit features a washer/dryer, wireless internet, central air conditioning and all the other...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 8
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    Paradise1 / 26
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 August 2017
    Beautiful stunning and breath taking ! The view was beautiful. House was clean upon arrival, very spacious! Loved the kitchen. The bedrooms were very clean and spacious! Loved...
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    About this property
    If you're looking for that special vacation home that offers everything you'll need, look no further. Paradise offers all top-of-the-line amenities including cherry wood floors, chef's kitchen and spacious master bedroom suite with custom bathroom and Jacuzzi tub. The main floor features a bright,...
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    Location Information
    Chincoteague Island, Virginia 23336
    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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    • 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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    Island Sunrise1 / 13
    (2)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • DVD Player
    • Air Conditioning
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    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 2 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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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Air Conditioning
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***3757 Willow Street***Completely renovated traditional home in town with bright cheerful rooms and offers all amenities. Pet friendly! Two bedrooms on second level of home and two walk thru third story bedrooms. Third story loft with 4 twin beds has a typical Traditional home steep staircase....
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    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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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • DVD Player
    • Air Conditioning
    • Internet Access
    • Waterfront
    Suitability
    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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come and enjoy this beautiful 3 bedroom villa! Conveniently located next to to pool, this ground-level condo allows you to walk right out from your balcony to the marina/dock. Enjoy all of the Chincoteague Island decor, spacious open floor plan, and the master bedroom suite featuring a private bath...
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    Location Information
    Chincoteague Island, Virginia 23336
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Bay Daze1 / 17
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Internet Access
    • Terrace
    • Cable/satellite TV
    • Balcony
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 August 2017
    A beautiful condo with nautical decor, comfortable beds, well-stocked kitchen, large refrigerator and 2.5 baths. Two balconies provide gorgeous views of the waterway, marsh and...
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    About this property
    Escape from the hustle and bustle of everyday life at this little slice of paradise nestled on the edge of the Chincoteague Bay! Bay Daze is a clean, comfortable and modern townhome (end unit) offering all the amenities you'll need for a perfect vacation! On the main level you'll find an open...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    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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    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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    Agape House1 / 15
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    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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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Great 2 bedroom, 2.5 bath townhome in Lighthouse Estates community off East Side Drive. This home features all amenities including central air, washer/dryer and new kitchen appliances. In addition, there is a community pool as well as water access and a dock (shared) to fish and crab from. This is...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Lavinder House1 / 35
    (1)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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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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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    NEW for 2017. This beautiful Victorian is located on Main Street and just a short walk to town. The 4BR home is spacious and very charming with much of it's original integrity still in place. Amenities include central heat & air, all appliances including washer/dryer, outside hot & cold shower,...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Quaint and charming island cottage with all the amenities! Located on the southern end of the island, Daisey Cottage offers everything you'll need for an enjoyable vacation - central a/c, dishwasher, WiFi, washer/dryer and more. And it's even pet friendly! Additional amenities include: bedding 2:...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    Water's Edge1 / 14
    (4)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Reviewed 24 May 2017
    Water's Edge is in a great location - right on the water and close enough to walk into town. The house was clean and equipped with anything you might need. As mentioned in...
    Reviewed 17 October 2016
    This recently renovated home features an open floor plan with wrap around windows facing out to the water. The small watch tower at the top of the house has stunning views and...
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    About this property
    Water's Edge is an adorable Bay Front cottage in walking distance to Chincoteague's Historic Downtown. You'll be impressed by the charm of this home from the time you pull in the driveway. On the first floor you'll find a full bathroom with an open great room with expansive bay views. There is a...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    This lovely vacation rental home features 3 bedrooms and 2 bathrooms, including a 1st floor master suite with a queen bed. Blissful Way is very bright and airy with a large living room/Dining Area. Off of the kitchen is a screened porch great for family bar-b-ques. Upstairs you'll find two more...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Assateague Light1 / 11
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed 25 August 2012
    Assateague Light is a very nice first-floor waterfront condo facing the Assateague Channel. The view from the deck is spectacular. When we were looking for vacation rentals on...
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    About this property
    This modern 2 bedroom condo located on the first floor features a master bedroom suite with a king bed, private bath and sliding glass door to the waterfront deck. The second bedroom has two twin beds with a full bathroom across the hall. This shared bath offers a walk in shower and washer/dryer....
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    Chincoteague Island, Virginia 23336
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    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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    Marsh Point1 / 13
    (3)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Reviewed 20 June 2015
    I have been to Chincoteague Island on many occasions, but this was the first time I have stayed at March Point. It is a little out of town, but there was very little traffic and...
    Reviewed 1 January 2015
    We love this location and this was our second trip to this set of townhouses, though last time through a different rental company. The property was clean, nicely appointed, and...
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    About this property
    Wonderful 2 bedroom townhome that features a great screened porch off the living room, large bedrooms (including master bedroom suite) and second-level screened porch off one bedroom. Full ensemble of appliances, central air, water access, private pier (shared by other units), and more! New...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 8
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    Misty's Thicket1 / 16
    (2)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Reviewed 28 September 2017
    Our family's second visit to Misty's Thicket was just as perfect as our first. Very comfortable house and the dock for crabbing is where we spend most of our time. We caught...
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    About this property
    Located on South Ridge Road, this lovely town-home features a private pier, central air conditioning, and galley style kitchen complete with a dining area and all necessary appliances. The cozy living room leads you onto one of two screened in porches perfect for unwinding with family and friends....
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Bay Dreamer is a spacious 3 bedroom duplex home with multiple porches and decks and spectacular sunset views, just minutes from downtown. When you enter the home you'll find a furnished rec room. The second floor features an open living room (queen sleeper sofa), dining area and kitchen. There is a...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    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, 3 Bathrooms, Sleeps 8
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    Donovan's Reef1 / 15
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Reviewed 11 August 2014
    Just returned from one of the best vacations ever. This house was nice and big. There were 8 in our party and there was plenty of room to speed out. The kitchen was well...
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    What a great house and it is PET FRIENDLY! Donovan's Reef is a classic home that offers large living spaces and bedrooms. On the first floor the original wood floors will guide you through a beautiful dining room (will seat 8 comfortably), right into a well appointed living room and den plus...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    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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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Abbie Thornton Cottage1 / 19
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Reviewed 25 August 2015
    My husband and I stayed at Abbie Thornton cottage in August 2015 and are SO happy we booked this place! It was absolutely wonderful, from the screened in porch (perfect spot...
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    About this property
    This charming Chincoteague cottage was built in the 1930's and is located directly across the street from the Chincoteague Bay. Abbie Thornton Cottage has kept much of the original integrity, but has been lovingly restored to offer all the modern comforts of home. There's a cozy screened porch off...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    About this property
    Comfortable, pet friendly home on large, side-creek lot with fantastic views from both the front and back of house! Excellent crabbing from dock! (Property sits on creek only suitable for kayaks, canoes and crabbing.) Just a short distance to Memorial Park and Fairgrounds. 2 living room areas, 2...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
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    About this property
    ***FEATURED SPECIAL - DON'T MISS OUT ON THIS SPECTACULAR DEAL! BEAUTIFUL WATERFRONT CONDO FOR $2000 A MONTH SEPTEMBER - NOVEMBER - You can't beat this price! If you are looking for a long stay for fun or coming for work, this condo is perfect! Has everything you need, including linens and...
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    Chincoteague Island, Virginia 23336
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Lighthouse Pointe1 / 15
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    One of East Side's most popular rentals! Features include open floor plan with waterside balcony downstairs, and a spacious third level master bedroom suite with private waterside balcony. All levels have balconies or deck! Very conveniently located - close to Memorial Park, restaurants and marina....
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Charlotte's Morning Sun1 / 26
    (1)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    About this property
    Set in the boutique residential community of Oyster Bay II, ‘Charlotte's Morning Sun’ is a stunning 5-star waterfront home that offers unobstructed water views and breathtaking vistas of Oyster Bay. Flowing generously over two levels, Charlotte features 4.5 bathrooms and 4 light-filled bedrooms,...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    ***6153 Marsh Island Drive-Marsh Island*** The owners of this new vacation rental have taken special care to provide their guests with many extras, including 1 person kayaks, beach items and a crab pot for your use. The view looking across Chincoteague Channel to Reed Memorial Park is...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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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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