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Villas in Chincoteague Island

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    Travellers to Chincoteague Island are booking August dates now. Secure your holiday rental today, and have the perfect trip.
    All 323 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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    Vacation House1 / 12
    (10)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    SA Waterfront  Views, Pier at this Park Rental!!!1 / 19
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Sea Heart & Soul, Waterfront Memorial Park Rental1 / 32
    (8)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Waterfront
    • Ocean Views
    • Patio
    • Satellite TV
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    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 4 weeks ago
    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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    Tranquil Shores - Relaxation With a Water View1 / 30
    (2)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 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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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beautiful Chincoteague Island retreat1 / 15
    (6)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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    Spacious, historic Chincoteague Is. vacation house1 / 13
    (7)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Reviewed 2 weeks ago
    We really enjoyed our stay - location was great, close to water and downtown. We loved the sunset views. The sandwich store is cross the street, very convenient. If you want a...
    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...
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    About this property
    Totally updated but traditional "home away from home" facing the Chincoteague Channel on Chincoteague Island, minutes from the quaint downtown and the Assateague National Seashore and Wildlife refuge. Relax in this spacious, clean, and beautifully furnished home with water views of the sunset from...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    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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    • 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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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 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
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 August 2016
    Good:- Clean, comfortable and functional- Location walkable to Main St shops and a bowling alley- Window air conditioners worked wellCould be improved:- Owner's...
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    About this property
    Cute, colorful 2 bedroom cottage with front and back porches. Walking distance to charming old town Main Street shops and restaurants. Back yard with grill and picnic table. Outside shower. Have coffee on the sunny back porch overlooking private back yard. Lots of windows. Wifi. DVDs for...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    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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    " TEAGUERS DELIGHT " Upscale Island Home with HOT1 / 16
    (4)Excellent
    2 Bedrooms, 4 Bathrooms, Sleeps 15 Quick 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
    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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    Assateague WATERFRONT CABANAS with a grand view!1 / 14
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • 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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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Agape House1 / 15
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Air Conditioning
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 June 2016
    We have been vacationing on Chincoteague for years and Love everything about it, This is a great house with lots of room we had two adults and four teens and it worked out...
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    About this property
    A great three bedroom home with a convenient in town location - 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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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Green Heron1 / 10
    (1)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Balcony
    • Terrace
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 July 2016
    Was very nice house Had some nice upgrades in kitchen. Bedrooms and baths met our needs. Close to beach and town attractions.. Only drawback we found was no wifi or even...
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    About this property
    ***4560 Shelley Cove Lane - Smugglers Cove***Private, secluded neighborhood. Very natural wooded setting with water access available. Next door to Pine Cove Place and Serenity Now. Water access is for kayaks and canoes. 2 bedrooms and 1 bath downstairs/2 bedrooms and 1 bath upstairs.***This...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Grill
    • Satellite TV
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Leave all of your worries behind when you stay at this marvelous 3-bedroom, 2-bathroom Chincoteague Island vacation rental house! Boasting space to sleep 8 guests, water views and a secluded canalside location with private pier, this quaint Virginia property will allow you to leave all your...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sunset Bay Villa 1111 / 16
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Grill
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 September 2016
    This place is really niiice!! Very spacious, modern kitchen.nice size bedrooms. Night time view off the living room/bedroom deck beautiful! It's very peaceful. I enjoyed...
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    About this property
    This 3 bedroom 2 bathroom luxury villa features a first floor, open floor plan villa for easy access and it is dog friendly. The first bedroom offers a twin trundle bed, the second bedroom has a queen bed and Master has a queen bed with a private bathroom and access to the waterfront deck. The...
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    Chincoteague Island, Virginia 23336
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Casa Bella1 / 15
    (3)Average
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, 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
    • Air Conditioning
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    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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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
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    Smoking allowed
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    ***6368 Pine Drive-Piney Island***Brand new Piney Island home. Spacious design open and bright with large screened porch and two covered porches offer views of Assateague in the distance. Close to Edie's Folly. Acess to community boat dock.***This Property provides Linens & Towels.***Bed Sizes: 2...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sunset Bay Villa 2031 / 15
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 September 2016
    My family and I were extremely satisfied with our stay at Sunset Bay Villa 203. The unit is tastefully decorated without being beach tacky.. The furniture is relatively new...
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    About this property
    Villa 203 is a new unit that has been professionally decorated and offers five-star luxury. Spacious and accommodating, the gourmet kitchen is perfect for cooking your favorite meals. It's well stocked and ready for your handiwork. There are three bedrooms, including a master bedroom suite with...
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    Chincoteague Island, Virginia 23336
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 May 2017
    Nicely updated bath. Great yard. Delightfully bright screened porch. Comfortable queen mattress. Quiet location with beach road easily accessible by bike for shopping...
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    ****6389 Circle Drive****Comfortable Island home packed with amenities. Sea Pines offers a nice shady yard and back screened porch in a quiet neighborhood. HD Flat Screen TV. Offers WiFi and Wired High Speed Internet and Charcoal Grill! Bathroom Newly Renovated for the 2017 season*** Close to...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    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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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    ***5348 Oak Drive-Piney Island***Tucked away in Piney Island Just minutes from Assateague's nature trails and beach. Wireless internet and water access for canoe and kayak. Pet Friendly! New bedroom and bathroom added in 2013. All bedrooms on same level.***Bed Sizes: 1 Queen, 1 Double, 2...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    East Wing1 / 12
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Balcony
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    Pet friendly
    Kid friendly
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    ***5159 Deep Hole Road***This charming island cottage built in 1920 features wood plank floors, open-beam ceilings, a screened-in porch and a large yard. Beautifully restored, East Wing is within walking distance of Little Oyster Bay, a boat launch, playground,restaurans and the best ice cream...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Eagle's View1 / 38
    (5)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Balcony
    • Internet Access
    • Terrace
    • DVD Player
    • Satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 June 2017
    This beautiful home on the water was very relaxing. We stayed here over Memorial weekend and although it rained half of the time, we still were able to catch crabs two nights...
    Reviewed 14 March 2017
    Eagle’s View is a piece of paradise! My wife and I have been coming to Eagle’s View for many years, and each time is a renewing experience. The views from the house and...
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    About this property
    Eagle's View is a luxury vacation rental overlooking the Assateague Island Channel and lighthouse. Fully equipped for comfort and convenience, this house is your home base for quick access to beaches, Eastern Shore attractions, and natural beauty. In addition to basking on the unspoiled beaches,...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    ***6242 Church Street***Proud 3 story Traditional home located at the edge of town is rich in detail and history of the island. Beautiful renovations make this home just right for the whole gang. Just a few steps and walk to shopping and waterfront downtown plaza. Spacious rooms and large dining...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Half Shell1 / 7
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Terrace
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    Pet friendly
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    ***5277 Oyster Court- Oyster Bay I ***Oyster Bay I home will delight you with it's spacious bedrooms and lovely back sunroom. Small screen porch in front and a fish cleaning table below the home is set-up to enjoy. Offers wireless internet and satelite tv.***Bed Sizes: 2 Queen, 2 Twin, and 1 Queen...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Tall Pines1 / 8
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    We stayed at Tall Pines on the advise of a friend. She said it was small, but nice.The house is all we needed as a family of four. The queen bedroom was bright and airy. The...
    Reviewed 29 August 2015
    Pros: Nestled in pine forest, well shaded so that AC was not necessary for most of our 2 week stay (esp when we could borrow fans from the management company). Very quiet...
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    About this property
    Located in lovely Piney Island within a short bike ride to the beach. This single story 2 bedroom, 1.5 bathroom house offers a large screened porch, fully equipped kitchen and spacious living room. Piney Island offers community water access great for launching kayaks/canoes. To top it all off, Tall...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    ****6206 Marsh Island Drive Unit #1***Wonderful effiencency condo unit located on Marsh Island. Enjoy some of the best water views and sunsets on Chincoteague. Fully equipped effiencincy kichen and laundry area. Shared pier and waterside picnic area. Comfortable and affordable with private...
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    Chincoteague Island, Virginia 23336
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    ****4379 Ridge Road****Lovely 2 bedroom home conveniently located on Ridge Road, not far from Maddox Blvd, with many great island attractions. Perfect house for a family of 4! This house offers extra space in the large sunroom. Bright and airy, the sunroom works for both cool and warm weather. The...
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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, 2 Bathrooms, Sleeps 8 Quick View
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    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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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    ***5104 Blake Point Road****Goose Bay tucked away off the northern end of Main Street offers a tranquil and serene location with outstanding waterviews and sunsets over the Chincoteague Bay and ponds. First Floor bedroom and two additional bedrooms with lof/sitting areat on second level. Very...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Barbie House1 / 12
    (5)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    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...
    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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    An Unfettered View1 / 25
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Reviewed 26 May 2017
    We try to visit the Eastern Shore near Assateague once a year in May before the summer crowds come in. We'd usually tent camp at Assateague seashore or Toms Cove but this year...
    Reviewed 13 September 2016
    This place is absolutely EVERYTHING you could hope for on vacation. The home is immaculately clean and lots of room. The well-kept , private dock is an exciting and successful...
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    About this property
    This beautiful 2BR ranch home has a quiet, out-of-the-way location on little Oyster Bay. The views of the bay are beautiful and expansive with a long pier straight from the back deck its perfect for crabbing, kayaking & canoeing. An Unfettered View features all amenities including a private master...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Island Sunrise1 / 13
    (1)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Reviewed 2 February 2014
    You should know that this is a duplex! We did not realize this and would not have been happy about it in peak season but the other half was empty so it was fine. I want to say...
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    About this property
    Island Sunrise is gorgeous 3 bedroom, 2.5 bathroom duplex home located in desirable Piney Island. Not only is this house pet friendly but it offers a deep water boat dock and 3 spacious decks. The views of Assateague Island and the Assateague Channel truly are second to none! Additional amenities...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    This beautifully renovated 4 bedroom, 2 bathroom home could be the ideal vacation home for your family and/or friends. Located on Oak Dr in Piney Island this home is an easy bike riding distance to the beach and trails of Assateague Island. Aramabad has a completely renovated kitchen with granite...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Located very close to town, Bay Breeze will remind you of summer vacations as a child. This 3 bedroom, 2 bath homes sleeps 6 and has a washer & dryer, window a/c, and a ton of charm! Comfortable and affordable - this may be your spot at the beach! Additional amenities include: laundry: washer &...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    This Piney Island gem, with it's beamed centrally sky-lit vaulted ceiling, is dramatic and inviting at the same time. Come relax! Enjoy the peace and tranquility in this 3 bedroom, 2 bath home. Amenities include spacious decks with snipet water views. There is community water access - a creek that...
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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, 1 Bathroom, Sleeps 5 Quick View
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    About this property
    ***5421 Deep Hole Road -downstairs apt***Secluded, quiet location with lots of yard for a pet. Pet Friendly!***Bed Sizes: 1 Queen, 1 Double, 1 Sleep Sofa***Prime Season Rates: $550 weekly/$110 per night.Off Season Rates: $400 weekly/$80 per night. Additional amenities include: a/c: wind,...
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    Location Information
    Chincoteague Island, Virginia 23336
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Sea Treasure1 / 12
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed 4 days ago
    Our first reaction walking in was relief! I booked in very late spring when there were next to no properties available so the whole way here we were holding our breath, hoping...
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    ***3400 Ridge Road***Lovely 2 Bedrooms, 1.5 Baths duplex with water views. This duplex overlooks Assateague Island with great views for the Pony Swim. This is the Best way to watch the Pony Swim and not move from your porch! Sit and enjoy the views from 2 porches. The screened porch is off of the...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    ***6751 Megan Lane***Spacious updated duplex with Screened Porch, W-iFi and Outside Shower. Within walking distance to Maddox Blvd. with shopping, restaurants and attractions.***Bed Sizes: 2 Queen, 2 Twin***Prime Season Rates: $780 weekly/$156 per night.Off Season Rates: $575 weekly/$115 per night....
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Surf Haven1 / 18
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Reviewed 20 April 2017
    Very clean, comfortable beds, all working amenities , great big flat screen TV and sound bar, very cozy cottage . Feels like you are on vacation as soon as you walk in!
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    About this property
    Looking for a relaxing beach vacation? Look no further! Enjoy a relaxing stay in this beautifully decorated island cottage. A quiet location while to get the much needed ; not to mention the extras such as WIFI and a Nintendo Wii! This quaint cottage offers two bedrooms and large climate controlled...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    Bay Mist is a nice two bedroom town home that features water and lighthouse views. The first floor has a large dining/kitchen area, living room with TV and a half bath. Upstairs features a master suite bedroom with private balcony that offers lighthouse/water views, as well as a second full bath...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Island Time1 / 8
    (1)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    ***7203 Bunting Road***Bright and open townhouse with private patio area and gas grill!! Offers nice wetland views. Close by is Island Escape and in walking distance to Firemans Carnival.***Bed Sizes: 1 Queen, 1 Double, 1 Bunk (2 Twins), 1 Queen Sleep Sofa.***Prime Season Rates: $625 weekly/$125...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    About this property
    ***3402 Ridge Road***Lovely 2 Bedrooms, 1.5 Baths duplex with water views. This duplex overlooks Assateague Island with great views for the Pony Swim. This is the Best way to watch the Pony Swim and not move from your porch! Sit and enjoy the views from 2 porches. The screened porch is off of the...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Tastefully remodeled beach home featuring a reverse floor plan and spectacular views of the Assateague Channel and Lighthouse! Located on the popular East Side of Chincoteague Island, Channel View is conveniently located near a public boat ramp, restaurants and Memorial Park. And you're about a...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 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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    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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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    ****6204 Poplar Street****Island Cottage has a great in town location! Easy walk to historic downtown's shops and retaurants. Perfect for a budget frienldy vacation. Has WiFi.***This Property accepts Dogs 35lbs and Under Only.***Bed Sizes: 1 Queen, 1 Double, 1 Twin.***Prime Season Rates: $575...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    ****5303 Meadow Drive****Well appointed rancher in Piney Island, with large screened porch and private den with sleep sofa. Offers bicycles and water access!! Recently added all new appliances and floors for 2015 season.Very close to Assteague Island.*** Bed Sizes: 1 Queen, 1 Double, 2 Twin, 1...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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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