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Chincoteague Island Holiday Rentals

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    All 311 Rentals in Chincoteague Island
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    Travellers to Chincoteague Island are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    31 Reviews
    2 Bedrooms, Sleeps 6Quick View
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    4 Reviews
    3 Bedrooms, Sleeps 6Quick View
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    6 Reviews
    3 Bedrooms, Sleeps 6Quick View
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    9 Reviews
    3 Bedrooms, Sleeps 8Quick View
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    • Washer
    • Air Conditioning
    • Wi-Fi
    • Porch
    • Balcony
    • Grill
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed 3 October 2016
    Beautiful vacation home. Everything was exactly as listed. Peaceful and comfortable! The owner was very quick to respond to email and phone call. I would highly recommend...
    Very good of 5 bubbles
    Reviewed 21 September 2016
    The house had a nice open layout on the downstairs. We had 2 families with three kids (4 year old, 3 year old, and 6 months old) and one other adult. We all fit nicely, the...
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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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    1 Review
    3 Bedrooms, Sleeps 6Quick View
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    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Grill
    • Waterfront
    • Satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed 4 weeks ago
    Thank you so much Shawn and Joe for sharing your beautiful home with us and our dogs. We were two couples from DC looking for a local retreat out of the city with our dogs...
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    About this property
    Peaceful 3 bedroom/2 bathroom home located directly on Eel Creek. Appreciate the natural beauty of Chincoteague Island with gorgeous nature views from both the lower level screened in porch as well as the balcony off of the master suite. Enjoy relaxing mornings with the sunrise and breeze filled...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Review
    2 Bedrooms, Sleeps 4Quick View
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    • Air Conditioning
    • Satellite TV
    • Private Garden
    • Washer
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Very good of 5 bubbles
    Reviewed 26 August 2016
    Good: - Clean, comfortable and functional - Location walkable to Main St shops and a bowling alley - Window air conditioners worked well Could 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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    1 Review
    3 Bedrooms, Sleeps 6Quick View
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    • Patio
    • Ocean Views
    • DVD Player
    • Washer
    • Air Conditioning
    • Waterfront
    • Satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    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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    41 Reviews
    4 Bedrooms, Sleeps 10Quick View
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    • Air Conditioning
    • Grill
    • DVD Player
    • Wi-Fi
    • Patio
    • Parking
    • Porch
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed 11 April 2017
    Staying here during spring break has become a tradition in our family! We love everything about this place! The location is great, the amenities were great and we enjoyed...
    Excellent of 5 bubbles
    Reviewed 1 April 2017
    What a wonderful little place to get away from it all for a few days! The owners are very friendly and respond almost instantly. We couldn't have chosen a better home to stay at...
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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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    4 Reviews
    2 Bedrooms, Sleeps 15Quick View
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    • Grill
    • Parking
    • Satellite TV
    • Hot Tub
    • Washer
    • DVD Player
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed 22 July 2016
    This was our 2nd year . this house is perfect for a large family vacation tim and Collen keep this clean and have a well stock kitchen every thing you need is there house is...
    Excellent of 5 bubbles
    Reviewed 31 August 2015
    We have been visiting Chincoteague for over 40 years. We have rented many houses on the island but this home is truly a home away from home. This was our first time using VRBO...
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    About this property
    Fresh redo on this spacious and comfortable home, new carpet, flooring, furnishings, mattresses, granite counter tops, tile work and more !<BR> This house has extensive accomadations, two and a half bathrooms and an outdoor shower and foot washing station make as well as a private outdoor hot tub...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 4 Bathrooms, Sleeps 15
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    6 Reviews
    4 Bedrooms, Sleeps 8Quick View
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    Pet friendly
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    Smoking allowed
    Excellent of 5 bubbles
    Reviewed 9 November 2016
    I can't tell you how much we enjoyed staying in this wonderful home. It had everything we wanted with the exception of a washer and dryer. It was spacious, warm and inviting. We...
    Excellent of 5 bubbles
    Reviewed 26 August 2016
    We rented this house for a week in August. Our extended family included myself, my husband, my two teenagers, and my mother and stepfather. The house (four bedrooms) had plenty...
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    About this property
    Totally updated but traditional "home away from home" facing the Chincoteague Channel on Chincoteague Island, minutes from the quaint downtown and the Assateague National Seashore and Wildlife refuge. Relax in this spacious, clean, and beautifully furnished home with water views of the sunset from...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    44 Reviews
    4 Bedrooms, Sleeps 10Quick View
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    • Ocean Views
    • Patio
    • DVD Player
    • Wi-Fi
    • Waterfront
    • Air Conditioning
    • Satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    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...
    Excellent of 5 bubbles
    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. Member, Chincoteague Chamber of Commerce Pets subject to approval and an additional fee. See our DeepHoleCreek site for more info and photos and rates.! Scroll down to email Blair & Martha (owners) for quote. Or Call Blair & Martha at the number listed for us under...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    Studio, Sleeps 7Quick View
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    • Internet Access
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Quaint and charming island cottage with all the amenities! Located on the southern end of the island, Daisey Cottage offers everything you'll need for an enjoyable vacation - central a/c, dishwasher, WiFi, washer/dryer and more. And it's even pet friendly! Additional amenities include: bedding 2:...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 1 Bathroom, Sleeps 7
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    2 Reviews
    Studio, Sleeps 6Quick View
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    • Grill
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Balcony
    • Terrace
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Very good of 5 bubbles
    Reviewed 10 September 2016
    We stayed here for a week with our two large dogs and an 18 month old. Loved the open floor plan and the furniture was comfy. Kitchen is well stocked and washer and dryer were...
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    About this property
    Cowboy Cottage is a pet friendly home conveniently located a block from Maddox Blvd and just a couple of blocks from downtown Main St. This ranch-style home has an open floor plan and is handicap accessible with a ramp to enter the house and bedroom/bathroom accessibility. There is a large screened...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bathrooms, Sleeps 6
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    1 Review
    Studio, Sleeps 8Quick View
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    • DVD Player
    • Air Conditioning
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    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 - easy walking 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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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bathrooms, Sleeps 8
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    Studio, Sleeps 6Quick View
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    • Waterfront
    • Internet Access
    • Grill
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our guests come year after year to relax and enjoy truly fabulous views of our famous Chincoteague Bay sunset! This roomy, attractively decorated home is surrounded by water views, wetlands and birds! Windrush boasts lots of outdoor space including two screened porches, open decks/balcony's and a...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bathrooms, Sleeps 6
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    1 Review
    Studio, Sleeps 8Quick View
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    • Air Conditioning
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed 28 September 2016
    My family and I were extremely satisfied with our stay at Sunset Bay Villa 203. The unit is tastefully decorated without being beach tacky.. The furniture is relatively new...
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    About this property
    Villa 203 is a new unit that has been professionally decorated and offers five-star luxury. Spacious and accommodating, the gourmet kitchen is perfect for cooking your favorite meals. It's well stocked and ready for your handiwork. There are three bedrooms, including a master bedroom suite with...
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    Location Information
    Chincoteague Island, Virginia 23336
    Condo/Apartment - 2 Bathrooms, Sleeps 8
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    Studio, Sleeps 10Quick View
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    • Waterfront
    • Internet Access
    • Air Conditioning
    • DVD Player
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    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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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bathrooms, Sleeps 10
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    1 Review
    Studio, Sleeps 8Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed 26 July 2015
    The rental was just perfect! We wished we could have stayed longer. The house was very clean, it was decorated so nice in a nautical theme. We were away from downtown...
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    About this property
    Nestled on a quiet cul-de-sac in a private community just off North Main Street (Oyster Bay II) is where you'll find the charming Cockleshell Cottage. This new 3 bedroom, 3 bathroom home boasts a first-floor master bedroom suite, all modern amenities and new furnishings. It is handlcap accessible....
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bathrooms, Sleeps 8
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    Studio, Sleeps 8Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Freshly updated Piney Island home with roots in island history. The kitchen and guest bedroom wing of this home were originally on Assateague Island, as part of the Assateague Village settlement! This pet friendly home boasts three bedrooms, large living and dining rooms, two full baths and a...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bathrooms, Sleeps 8
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    Studio, Sleeps 10Quick 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 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 - 2 Bathrooms, Sleeps 10
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    Studio, Sleeps 8Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    What a beautiful home! This classic downtown Victorian is perfect for your vacation. The spacious first floor offers a large living room, formal dining room, fully equipped kitchen screened porch and queen bedroom plus half bath. Upstairs you'll be welcomed by two large bedrooms one Master Suite...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bathrooms, Sleeps 8
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    Studio, Sleeps 6Quick View
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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 uninterrupted 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...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bathrooms, Sleeps 6
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    1 Review
    Studio, Sleeps 8Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely townhome rental features TWO great screened porches! One with a ceiling fan just off living room, large bedrooms, including a master bedroom suite, second-level screened porch off one bedroom and an outside shower. A full ensemble of appliances, central air, galley-style kitchen, water...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bathrooms, Sleeps 8
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    Studio, Sleeps 8Quick View
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    • Grill
    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Whispering Pines is a comfy 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, utilizing the sleep sofa in the living room. The open floor...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bathrooms, Sleeps 8
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    1 Review
    Studio, Sleeps 8Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    Very good of 5 bubbles
    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 Bathrooms, Sleeps 8
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    1 Review
    Studio, Sleeps 8Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed 25 July 2016
    We stayed here a few weeks ago. We had stayed in another house on the same street in a previous year- have been coming to the island for decades! The AC is COLD, the deck...
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    About this property
    Escape to the beach - come to this wonderful "Hidden Treasure" nestled within one of Chincoteague Island's most prestigous communities. Hidden Treasure features a great open floor plan downstairs, as well as the privacy of a separate den (with sleep sofa), full bathroom and bedroom (2 twins). A...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bathrooms, Sleeps 8
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    Studio, Sleeps 10Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Comfortable, pet friendly home on large, private side-creek lot with fantastic views from both front and back of house! Excellent crabbing from dock! (Property sits on creek only suitable for kayaks, canoes and crabbing.) Easy walking distance to Memorial Park and Fairgrounds. 2 living areas, 2...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bathrooms, Sleeps 10
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    1 Review
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    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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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 1 Bathroom, Sleeps 2
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    2 Reviews
    Studio, Sleeps 6Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed 3 weeks ago
    We stayed here for 2 nights and wished we stayed longer! It was my husband and I plus our 8 year old grandson and our dog and we all loved it! The screened in large porch...
    Excellent of 5 bubbles
    Reviewed 29 November 2016
    Four adults stayed here for an extended Thanksgiving Day weekend and took advantage of the location to explore a Chincoteague Island and nearby Assateague as well. The rental...
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    About this property
    Oyster Cove is a beautiful three bedroom, two bath home with an open floor plan, plenty of windows, and outstanding views of Oyster Bay! Relax with a book on the giant screened porch or catch some sun on one of the home’s several open decks. At nearly every turn the waters of Chincoteague surround...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bathrooms, Sleeps 6
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    1 Review
    Studio, Sleeps 6Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    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 Bathrooms, Sleeps 6
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    1 Review
    Studio, Sleeps 8Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    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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    About this property
    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 - 2 Bathrooms, Sleeps 8
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One of our newest Captain's Cove listings! Lakeside is a clean, comfortable home situated on a partially wooded lot that backs up to a wonderful lake. Guests can use the lake for canoeing and kayaking! You'll enjoy watching the ducks and geese in their natural habitat, and they'll even come up...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bathrooms, Sleeps 8
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    1 Review
    Studio, Sleeps 8Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed 30 August 2013
    My favorite vacation home ever! This house was beautiful and you get that "beach feeling" as soon as you pull in. The bay is within view from the house and the beach is a mere...
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    About this property
    A very nice contemporary home located in Oyster Bay I. Located next to the community boat ramp - you have access to the water and the kids can fish and crab from the dock areas. This house has an outdoor ramp to the ground level. Don't miss out on the great screened porch for a family dinner. Bed...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bathrooms, Sleeps 8
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    1 Review
    Studio, Sleeps 6Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed 29 March 2017
    We have been coming to Chincoteague Island since 1988 and this is the best house we have been to. The décor is sweet and thoughtful. All the little touches are lovely and the...
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    About this property
    Wow... What a show piece! On Island Time is exactly what you expect in your beach rental, from the bright and fun decor to the spacious and bright floor plans, all of this wrapped in a traditional Eastern Shore Home. The front enclosed porch is great for reading or just relaxing in the afternoon...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 1 Bathroom, Sleeps 6
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    3 Bedrooms, Sleeps 8Quick View
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    • Washer
    • Air Conditioning
    • Housekeeping Included
    • Ocean Views
    • 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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    5 Bedrooms, Sleeps 10Quick View
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    • Satellite TV
    • Patio
    • Grill
    • Washer
    • Waterfront
    • Air Conditioning
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    2 Reviews
    Studio, Sleeps 8Quick View
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    Pet friendly
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    Smoking allowed
    Excellent of 5 bubbles
    Reviewed 13 October 2015
    This two-floor unit offered peace and quiet. The quality and amenities were good and more room than we expected. The three bedrooms downstairs included three full baths...
    Average of 5 bubbles
    Reviewed 1 August 2011
    We have never been to Chincoteague to know the location of the house or amenities close by, but we were fortunate to be close to it all! The house was nice, after we did the...
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    About this property
    Captain's Loft is located just a short walk to Maddox Blvd! Close to everything, but situated perfectly for a quiet and relaxing stay. This duplex offers a bathroom with every bedroom, four televisions and internet access. The second level is an open great room with living room, dining area and...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bathrooms, Sleeps 8
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    2 Reviews
    Studio, Sleeps 11Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful waterfront contemporary perched on the edge of Assateague Channel. Enjoy breathtaking vistas of Assateague Island, the lighthouse, the wild ponies and the abundant wildlife. This spacious home boasts a complete line of amenities including a 600' pier/dock with deep water access (17'), and...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bathrooms, Sleeps 11
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    3 Bedrooms, Sleeps 8Quick View
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    • DVD Player
    • Patio
    • Housekeeping Included
    • Grill
    • Washer
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy what nature has to offer in this quiet but active resort island on Virginia's Eastern Shore. The atmosphere is a relaxed one yet there is an extensive amount of activities for vacationers. From surf, bay or offshore fishing to kayaking, sunbathing, bird watching, hiking and biking nature...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Reviews
    Studio, Sleeps 6Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Very good of 5 bubbles
    Reviewed 29 August 2013
    Our first vacation to chincoteague and we decided to stay here. Price was right and it had all the things we needed. Great things about this house are the screened in patio...
    Excellent of 5 bubbles
    Reviewed 11 August 2013
    We had the time of our lives! The house was decorated so beautifully and well maintained! We just loved the back yard and the fact that we were able to barbeque was an added...
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    About this property
    Historic in town home is an easy walk or bike to downtown or Maddox Blvd. Nicely decorated with three bedrooms. Living room has abundant seating a flat screen TV and DVD player. Wireless internet service is provided. The enclosed porch with sliding windows allows for room to spread out in any...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bathrooms, Sleeps 6
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    Studio, Sleeps 6Quick View
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    • Grill
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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 Bathrooms, Sleeps 6
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    3 Reviews
    Studio, Sleeps 6Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    Very good of 5 bubbles
    Reviewed 24 August 2015
    My three middle aged friends and I spent a week on Chincoteague Island. Casa Bella is beautiful on the inside and the outdoor shower in back is wonderful. The location is...
    Excellent of 5 bubbles
    Reviewed 8 July 2013
    We booked our stay prior to the reading the other review. I worried the whole way to Chincoteague that we had made a mistake after reading that review. We could not have been...
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    About this property
    Very popular pristine beach bungalow located within a short walk to Main Street, downtown waterfront park, shopping and dining. Fully stocked kitchen, nicely landscaped yard, backyard deck, large outside shower (with hot/cold water), screen porch off the kitchen, large fenced back yard. New...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 1 Bathroom, Sleeps 6
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    1 Review
    Studio, Sleeps 8Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    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 - 2 Bathrooms, Sleeps 8
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    5 Reviews
    2 Bedrooms, Sleeps 4Quick View
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    • Air Conditioning
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Average of 5 bubbles
    Reviewed 15 September 2016
    We've been to Chincoteague many times and love the fantastic beach and laid back, quiet town. We need to bring our dog so we always stay in dog-friendly properties. Therefore...
    Excellent of 5 bubbles
    Reviewed 8 July 2014
    I traveled to Chincoteague with my husband and 2 children ages 12 and 14. The Barbie House was perfect for our needs. It was on Main Street but this end of Main Street was...
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    About this property
    ***5052 Main Street***Enjoy the sunsets from this new wateview home, tucked away off North Main Street. Private setting.***Bed Sizes: 1 Queen, 2 Twins***Prime Season Rates: $900 weekly/$180 per night.Off Season Rates: $700 weekly/$140 per night. Additional amenities include: a/c: cent,...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, Sleeps 6Quick View
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    About this property
    ***5348 Oak Drive-Piney Island***Tucked away in Piney Island Just minutes from Assateague's nature trails and beach. Wireless internet and water access for canoe and kayak. Pet Friendly! New bedroom and bathroom added in 2013. All bedrooms on same level.***Bed Sizes: 1 Queen, 1 Double, 2...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Reviews
    Studio, Sleeps 7Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    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 - 2 Bathrooms, Sleeps 7
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    2 Reviews
    Studio, Sleeps 8Quick View
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed 3 August 2014
    This was a wonderful place to stay. The pictures don't do this place justice. Definitely will stay again.
    Average of 5 bubbles
    Reviewed 26 August 2013
    third floor rental with view of marina and bay...good living room couches....nice mbr furniture (if thats important)...but, I found it a struggle to find basic utensils in the...
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    About this property
    Villa 312 is a beautiful 3 bedroom villa featuring a master bedroom suite with luxury bath, gourmet kitchen with center island which is great for entertaining, laundry room with washer/dryer and a waterside balcony overlooking Chincoteague Bay. There are tvs in all the bedrooms, and a computer desk...
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    Location Information
    Chincoteague Island, Virginia 23336
    Condo/Apartment - 2 Bathrooms, Sleeps 8
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    4 Reviews
    1 Bedroom, Sleeps 4Quick View
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    Pet friendly
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    Smoking allowed
    Very good of 5 bubbles
    Reviewed 2 August 2016
    This is the perfect spot, for the price, in between the beach and town. The house can easily accommodate two adults and two pre-teens . The beds are not pillow tops by any means...
    Very good of 5 bubbles
    Reviewed 9 July 2016
    My husband and I just stayed at Cattail Cottage and were very happy with the accommodation s. i was a little worried about ants and there were none! The cottage was very clean...
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    About this property
    ****4150 Grumpy's Lane****Charming cottage located on a quiet, private lane. Close to town. Spacious sunroom addition! Newly added outside shower! Nearby are Smitty's Paradise.***Bed Sizes: 1 Double, 1 Double Sleep Sofa***Prime Season Rates: $550 weekly/$110 per night.Off Season Rates: $400...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Reviews
    Studio, Sleeps 7Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed 13 September 2015
    What a great location and place. The location was right where anyone would want to be. On the side of the island so it was a short little walk/bike ride/drive to the sea. We...
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    About this property
    The house is located on Pine Drive on Piney Island, closest neighborhood to the beach and convenient for shopping and dinning on Maddox Blvd. This wonderful waterfront beach bungalow features a wrap around deck with views of Assateague and the light house. You can bring your boat, jet skies or...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 1 Bathroom, Sleeps 7
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    2 Bedrooms, Sleeps 6Quick View
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    • Balcony
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***6703 Megan Lane***Bright and spacious duplex located on private lane. In walking distance of many island attractions. Offers second floor master bedroom suite. 1 bedroom and 1 bath downstairs/1 bedroom and 1 bath upstairs. Nearby is Georges Retreat.***Offering WiFi***Bed Sizes: 1 Queen, 1...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    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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