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Chincoteague Island Holiday Rentals

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    Travellers to Chincoteague Island are booking September dates now. Secure your holiday rental today, and have the perfect trip.
    All 371 Rentals in Chincoteague Island
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    Waterman's Cottage1 / 21
    (36)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    SNUG HARBOR WATERFRONT COTTAGE with a stunning lighthouse view!1 / 49
    (36)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Vacation House1 / 12
    (12)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Sea Heart & Soul, Waterfront Memorial Park Rental1 / 32
    (8)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Waterfront
    • Ocean Views
    • Patio
    • Satellite TV
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 July 2017
    We had a wonderful time staying at the SHS. The owner was very friendly and acomodating. Our kids loved the playground right across the street! We cant wait to come back!
    Reviewed 20 June 2017
    The home is very beautiful, fully furnished and is located in a very nice neighborhood. It's a little out there from town but very quiet and nice. I would highly recommend.
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    About this property
    SEA HEART&SOUL next to SEA ADVENTURE: This home offers 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, relax and enjoy, coolers, beach chairs, grill, beach toys, storage under...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Assateague WATERFRONT CABANAS with a grand view!1 / 14
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Terrace
    • Waterfront
    • Grill
    • Balcony
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 September 2016
    This is the most beautiful and most peaceful setting ever. Close to everything but far enough to enjoy peace and quiet. Sitting by the water, enjoying the view and ocean breeze...
    Reviewed 23 September 2016
    I was just hoping for a nice place on the water to relax but this rental and location way exceeded my expectations. I really wanted to be close to the water and when we arrived...
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    About this property
    Our waterfront cabanas are located right on Assateague channel on East side Rd. The property overlooks Assateague Island and the National Park and the Wildlife Refuge. You can see the Assateague Lighthouse and the famous wild ponies straight from the property right across the water. You can wake...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Beautiful Chincoteague Island retreat1 / 15
    (7)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Satellite TV
    • Porch
    • DVD Player
    • Parking
    • Washer
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 June 2017
    We greatly enjoyed our stay at this beach house. It was very neat and clean and had a fully stocked kitchen that met all our needs. The owner was very accommodating.
    Reviewed 16 April 2017
    This house was so nice and relaxing. Located on a cul de sac. Listen to nature on the patio. Cute ducks playing in the street. House felt very clean. The kids(and the adults...
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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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    Sea Adventure: Waterfront  Views, Pier at this Park Rental!!!1 / 19
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Ocean Views
    • DVD Player
    • Washer
    • Air Conditioning
    • Waterfront
    • Satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 July 2016
    We had rented both houses SHS and SA for our family/friends with kids. The house was very clean and comfortable for all. Very kid friendly, since it was just across from the...
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    About this property
    SEA ADVENTURE next to Sea Heart and Soul are 2 miles from Assateague Island and 5 miles from beach front fun. Check-in 4pm/ check-out 12pm. $229.00 per night. This home, right out your front door, has the coolest waterfront park ever!!! Chincoteague Veteran's Memorial Park, for the recreation of...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Spacious, historic Chincoteague Is. vacation house1 / 13
    (9)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    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...
    Reviewed 3 weeks ago
    The house is very comfortable and relaxing. Enclosed front porch is nice with partial water views. Decorated nicely!! Outdoor shower which is convenient, no laundry other than a...
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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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    Tranquil Shores - Relaxation With a Water View1 / 30
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Grill
    • Waterfront
    • Satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    Have been to Chincoteague many times and have always enjoyed our stay. Tranquil Shores will rank up there with the best of the best. Our dog loved the screened in porch and I...
    Reviewed 25 April 2017
    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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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Duck's Delight - Your Seaside Home Away From Home!1 / 20
    (42)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Air Conditioning
    • Grill
    • DVD Player
    • Wi-Fi
    • Patio
    • Parking
    • Porch
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Waterfront, 5 BR, 4 BA, Elevator, sleeps 101 / 48
    (1)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Satellite TV
    • Patio
    • Grill
    • Washer
    • Waterfront
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 June 2017
    Our family loved this home. It was spacious, comfortable, well appointed and oh that view. I ( the family chef) was very pleased with the state-of-the-art kitchen...I didn't...
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    About this property
    The Moorings North is an unique architecturally designed luxury 5 bedroom home in the heart of Chincoteague Island. The house is elegantly decorated and has mesmerizing panoramic views of Chincoteague Bay. It is conveniently located in walking distance to small shops, a coffee house, and...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    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
    • 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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    Epiphany on Deep Hole Creek - Waterfront & Dock - late August available!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
    • 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 Late August available! Pets subject to approval and an additional fee. See Deep Hole Creek site for more info and photos.! Scroll down to email Blair & Martha (owners) . Or Call Blair & Martha...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    GORGEOUS 3BR  WATERVIEW "GINCOTEAGUE ESTATE"1 / 19
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Satellite TV
    • Private Garden
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 May 2017
    This full size residence is perfect for a family or a couple. It is spacious and clean and offers a water view as well as tons of privacy. It is located directly across the...
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    About this property
    This beautiful estate is nestled on a gorgeous, large yard on Chincoteague Island. It has just been renovated so now it's ready for you to come and enjoy it! This spectacular house offers a nice living room with 50 inch plasma TV, sun room, spacious kitchen, three bedrooms and two full bathrooms....
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sand & Sea-renity1 / 32
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Porch
    • Grill
    • DVD Player
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 June 2016
    Truly lived up to its name. Very peaceful area with wonderful water views. Close to town and island attractions. Nicely furnished and well equipped. Traveled with a party of...
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    About this property
    Sand and Sea-renity is a Newly Listed, "Brand New", charming, calming, and relaxing, 4 bedroom, 3 and a half bath, central air conditioned home, that sleeps up to 8 people with 3 queen, and one day bed that can be used as 2 Twins or 1 King. Tucked away at the end of a quiet cul-de-sac in Oyster Bay...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Coco Banana on Chincoteague Island1 / 26
    (7)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • DVD Player
    • Air Conditioning
    • Grill
    • Satellite TV
    • Porch
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 May 2017
    Great location, very well stocked( ie. dish towels, cook ware, seasonings..) This rental is the nicest one I have stayed in and I have been coming to the Island for 20 +years...
    Reviewed 18 August 2016
    My family has declared that Coco Banana is the best 2 bedroom, 2 bathroom rental in Chincoteague! We love the layout of the house, the detail of the décor, the screened porch...
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    About this property
    COCO BANANA is a bright and spacious 2-bedroom, 2-full bath, central air conditioned home, located on a quiet dead-end street near the heart of town. It is just a short walk to historic Main Street where you can explore Chincoteague’s quaint gift shops, restaurants ice cream parlor and movie...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Assateague Overlook #21 / 15
    (3)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Wi-Fi
    • Satellite TV
    • Balcony
    • DVD Player
    • Air Conditioning
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 July 2013
    We had a great stay at Assateague Overlook #2. We travelled with our 3 kids (ages 4, 2 and 8 mos) during Pony Swim Week on Chincoteague. The rental was a great location. Not too...
    Reviewed 22 July 2013
    My husband and I came down for our honeymoon--this was our first visit to Chincoteague and we didn't know totally what to expect. I'm glad we chose to stay at this place as it...
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    About this property
    Assateague Overlook #2. is located on the eastside of Chincoteague just off the bank of the Assateague Channel. Enjoy watching the wild ponies from your balcony. Experience the wonderful breezes. Take in the breath taking views of Assateague Island and the historic Lighthouse. You are within a...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Patio
    • Grill
    • Parking
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Paradise by the Lighthouse1 / 8
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Terrace
    • Grill
    • Porch
    • Balcony
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 May 2015
    Paradise by the lighthouse is very decieving as from the outside it appears a little worn -but when you step into this good sized split sectioned home you will be amazed at the...
    Reviewed 12 July 2014
    We truly enjoyed our stay. The house was very clean and the decor made us feel right at home! Even the little odds and ends were not forgotten. If you needed something, it was...
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    About this property
    Paradise By The Lighthouse is located on the eastside of Chincoteague just off the bank of Assateague Channel. Enjoy watching the wild ponies from your balcony and experience the wonderful breezes and breathe taking views of Assateague Island and the historic Lighthouse. You are within a stone’s...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sidewalk's End1 / 14
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
    • Washer
    • Patio
    • DVD Player
    • Grill
    • Parking
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 July 2014
    This was an incredibly cute place and surprisingly spacious--large living room and master bedroom, comfortable area rugs. I was happy to see a bookshelf with a random...
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    About this property
    Sidewalk’s End is an adorable, 2 bedroom, 1 1/2 bath, central air conditioned cottage located in town for summer evenings spent strolling, shopping, playing miniature golf, exploring the many restaurants, and of course the ice cream parlors. The Comfortable living room with plenty of seating, is...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Joshua B. Jones Homeplace is a historic waterman's 19th century Victorian home. The home has been newly renovated but still has the beauty and charm of the original home. The home is located on Main Street and is within walking distance of of town to visit restaurants, movie theater and all the...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Terrace
    • Air Conditioning
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled beneath the tall pines is where you'll find this delightful Piney Island home. The Bird House features an open living room/kitchen/dining area, and extra "family" space in the private den. The many large windows throughout the home create a bright, airy atmosphere. Enjoy relaxing breezes on...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Satellite TV
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bayside Sunset, formerly known as Pine Warbler, is a 2 bedroom, 2.5 bath, centrally air conditioned townhome that sleeps up to six (6) people with 1 Queen, 2 Twin, and 1 Queen Sleeper Sofa. Upon entering the home on the first floor you will find a fully equipped kitchen with microwave &...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Our Sanctuary1 / 22
    (3)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Balcony
    • Terrace
    • Air Conditioning
    • Waterfront
    • Washer
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 July 2017
    This was by far one of the nicer rentals we've ever booked. It had just about everything you need for your vacation. There is a dock area in the back so that you can do some...
    Reviewed 19 August 2015
    This was a wonderful townhouse in a beautiful location. I can highly recommend it and we hope to return next year.
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    About this property
    Our Sanctuary is a Canal Front 2 Bedroom, 2 ½ bath, central air conditioned, town home that sleeps up to six (6) people with 2 Queen ( 1 Queen bed, 1 Queen Sleep Sofa), and 3 Twin Beds. Relax and unwind while enjoying the beautiful water views that the back yard, deck and balcony offer, or spend...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Silver Thatch in Chincoteague1 / 18
    (1)Excellent
    4 Bedrooms, Sleeps 9 Quick View
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    Amenities & Details
    • DVD Player
    • Washer
    • Grill
    • Patio
    • Outdoor Dining Area
    • Parking
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 August 2013
    Really enjoyed ourselves here. It was large enough with enough porches and separate areas to allow everyone space to themselves
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    About this property
    Silver Thatch is a wonderful place to enjoy a Peaceful Island Getaway. Enjoy family gatherings on the spacious deck or curl up with a good book in the screened in living area. Silver Thatch is a beautifully decorated 4 bedroom / 2 bathroom home located close to the Assateague Island National...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, Sleeps 9
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick 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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    Moorings South1 / 45
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 July 2015
    I just returned from a week in this lovely home with a family group of 7, including my father, who is disabled and can walk short distances with a quad cane but cannot handle...
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    About this property
    The Moorings South is a four bedroom, four bathroom, central air conditioned, luxury style vacation rental that sleeps up to eight people with 2 King/ 1 Queen/2 Twin beds, and is nestled directly on the deep water of the Chincoteague Channel for easy boating. This home has been built on a reverse...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Pier Pressure1 / 16
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • DVD Player
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
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    Pet friendly
    Kid friendly
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    About this property
    WATCH SPECTACULAR SUNSETS FROM THIS LUXURY TOWNHOME! This exceptionally beautiful 3 bedroom/2 bath luxury vacation rental home has central AC/heat and will accommodate 6 guests. Amenities include a designer kitchen, Jacuzzi tub & top of the line upgrades throughout the home. The master bedroom and...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
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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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    Mystical Sand1 / 9
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Reviewed 10 July 2017
    We (my wife, son, mother-in-law, wife's aunt, and myself) stayed here last summer. My son was only a year old so it was really only 4 full grown people. We loved the location...
    Reviewed 10 July 2014
    Loved staying at the Mystical Sand. Perfect for a romantic get away, 2 couples or a family of four.. Loved the outdoor shower, the gazebo and the kitchen has everything you need...
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    About this property
    ***6096 Taylor Street***Perfect retreat for the traveler on a budget! Tastefully decorated cottage with 36 inch television and within walking distance of shops and restaurants. Has outside screend gazibo! All bedrooms on same level.***Bed Sizes: 1 Queen, 2 Twin, 1 Queen Futon***Prime Season Rates:...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    " TEAGUERS DELIGHT " Upscale Island Home with HOT1 / 32
    (4)Excellent
    2 Bedrooms, 4 Bathrooms, Sleeps 15 Quick View
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    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beacon View is a beautiful 4 bedroom/ 3 full bathroom home located on the deep water of Assateague Channel. This vacationer’s dream has a gorgeous view of Assateague Island and the Lighthouse and includes a private deep water boat dock for fishing, crabbing or just relaxing and enjoying the...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    Bayberry is an inviting, 2 bedroom, 2 ½ bath, centrally air conditioned, canal front townhome that sleeps up to 6 people with 1 Queen, 1 Queen Sleep Sofa, and 2 Twin beds. This island getaway is the perfect spot for enjoying the Fresh Salt Air from the first floor deck or the second floor balcony...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Lighthouse Estates #31 / 22
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    • Shared Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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 within walking 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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    Agape House1 / 15
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Pet friendly
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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 - 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 - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Pet friendly
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    About this property
    As a classic Chincoteague-style home, Hopkin's House is situated on the East Side of Chincoteague Island and overlooks the Assateague Channel. You'll enjoy a wonderful, relaxing vacation at this 3 bedroom home; it's just a short distance from the public boat ramp, Memorial Park, a restaurant and...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    All Decked Out1 / 46
    (1)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Gorgeous home with a spectacular views.Amenities provided are fair to good, things like blankets bedspreads are in need of replacement. Lots of signs around as to how to lose...
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    About this property
    All Decked Out is a 4 bedroom, 3 full bath, central air conditioned, waterfront home that sleeps up to ten (10) people with 1 King, 3 Queen, and 1 Double Futon. Nestled along the banks of the Assateague Channel, you can enjoy panoramic views of Assateague Island and the Assateague Lighthouse from...
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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 6 Quick View
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    Smoking allowed
    About this property
    Homeport is a comfortable, inviting, 2 bedroom, 1 bathroom, centrally air conditioned home located on a quiet street within a short walk to town. Upon entering the home you are greeted by a large living room with a queen sleeper sofa, and a kitchen that opens onto the back deck and screen porch....
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Cockleshell Cottage1 / 14
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Pet friendly
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    Reviewed 24 May 2017
    This home was decorated beautifully and was more than roomy for the two of us plus our 2 yorkies. Loved sitting on the back screened in porch while reading or eating ice cream...
    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 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    • Housekeeping Included
    • Ocean Views
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    • Waterfront
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    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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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    ***6248 Ocean Boulevard***Walk to restaurants, shopping, etc. from this in town home. Nearby is Atlantic Delight and A Sea Change. WiFi Available. Upstairs offers a master suite with a private bathroom and 2 bedrooms and a full bath. 1/2 bath downstairs.***Bed Sizes: 1 Queen, 4 Twin***Prime Season...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Misty's Thicket1 / 13
    (1)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    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 - 2 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Melva’s Place is a warm and inviting retreat, located in the Heart of Chincoteague. Upon entering this 1 story home you are greeted by a Fully Stocked Kitchen, Dining Room, Large Living Room with a Queen Sleeper Sofa, 1 Full Bath, and 2 Bedrooms. The first Bedroom is furnished with a Double bed,...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    About this property
    ***6582 Church Street***Lovely spacious home with 2 enclosed sunporches. Large kitchen for those looking to cook. Nice back deck and 1st level bedrooms. 3rd bedroom is loft area. Close to town & shopping but very quiet and private setting. 2 bedrooms and 2 baths downstairs (includes master bed...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Waterfront
    • Air Conditioning
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    • Outdoor Dining Area
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lorna’s Dune is a 2 bedroom, 1 1/2 bath, central air conditioned home that sleeps up to 4 people with 1 Queen and 2 Twin beds. On the first floor you will find the kitchen that is furnished with stove, refrigerator, dishwasher, microwave, coffee pot, crock pot, pots and pans, dishes, glasses,...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, Sleeps 6 Quick View
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Peter’s House is situated in the Piney Island area. It is within ½ mile of Maddox Blvd., the road to Assateague Island and the beach. It is very convenient to and within walking distance of shops, restaurants, miniature golf and much more. There is off street parking at the house for three...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    About this property
    Quaint and charming island cottage with all the amenities! Located on the southern end of the island, Daisey Cottage offers everything you'll need for an enjoyable vacation - central a/c, dishwasher, WiFi, washer/dryer and more. And it's even pet friendly! Additional amenities include: bedding 2:...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    Whispering Pines1 / 15
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Reviewed 1 week ago
    Great location...close to harbor for flounder fishing! Enjoyed the bikes at the house. We visit Chincoteague on a regular basis. Just love the island!
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    About this property
    Whispering Pines is a 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 - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Joy's House1 / 15
    (1)Very good
    3 Bedrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 September 2013
    We loved our stay at Joy's House! My husband has been vacationing in Chincoteague since he was a young child and this our second year coming as a family of four. We wanted to...
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    About this property
    Joy’s House is a Charming, 2 bedroom, 2 ½ bath, Chincoteague Style, window air conditioned, water front home with stunning views of the Chincoteague Channel. This home is located close to the Curtis Merritt Harbor for the boating enthusiasts in the family. Breathtaking sunsets, cool salt breezes...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, Sleeps 6
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    Previous
    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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