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Chincoteague Island Vacation Rentals

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    Travelers to Chincoteague Island are booking May dates now. Secure your vacation rental today, and have the perfect trip.
    All 276 Rentals in Chincoteague Island
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    Vacation House1 / 12
    (15)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    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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    Spacious, historic Chincoteague Is. vacation house1 / 13
    (10)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Sea Heart & Soul, Waterfront Memorial Park Rental1 / 32
    (9)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Waterfront
    • Ocean Views
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 19, 2017
    We had a wonderful stay and the location couldn't have been better for our family. My husband was able to get up early to fish at the pier and I was able to let the kids sleep...
    Reviewed July 10, 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!
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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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beautiful Chincoteague Island retreat1 / 15
    (12)Very good
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Porch
    • DVD Player
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    • Washer
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 23, 2017
    The house was a good location, very close to a lot of stores and attractions. Very cute layout, with a stocked kitchen, screened porch, and a lovely breakfast nook. The beds and...
    Reviewed September 22, 2017
    Enjoyed our stay here. Cozy and close to downtown. All appliances and A/C functioned well (except the vacuum cleaner -- never figured that one out). Screened porch was...
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    About this property
    Come stay and relax at this quiet retreat. This listing is a newly remodeled home which is tastefully decorated. There are three color themed bedroom's; which have two queens and two twin sized beds. There is serenity all around you, come sit on the screened in porch and relax while listening to...
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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Key West Cottages1 / 4
    (2)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Balcony
    • Patio
    • Central Heating
    • Terrace
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 1, 2018
    Beautiful Cottages..Nicole is great!Just need to fix the bathroom door so,ya don't get locked in! :)
    Reviewed October 4, 2017
    This was an adorable little cottage with some fantastic amenities. The bed was really comfortable and the rain shower was nice. A full kitchen with coffee maker, dishes...
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    About this property
    Beautiful cottages located in the heart of Downtown Chincoteague with views of the Chincoteague Channel and Bay. The Key West Cottages are equipped with full kitchens, cozy living rooms, Queen bedrooms and large tiled showers. Amenities such as an indoor pool, hot tub and outdoor pool next door...
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    Chincoteague Island, Virginia 23336
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Dancing Water View1 / 9
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Beautiful views of Asseteague Island with lighthouse, ponies (with binoculars), fun dock to crab, kayak, or keep boat. Furniture and beds very comfortable and kitchen with...
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    About this property
    New Chincoteague rental with panoramic views of Asseteague Island, ponies and lighthouse. Enjoy sunsets, crab, fish, swim, and kayak from shared dock with optional boat slip. 2 bedrooms (full and 2 twin bunks) (queen) pullout queen couch in living room. One full bathroom. Newly renovated with new...
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    Chincoteague Island, Virginia 23336
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    Cozy cottage near Old town Fishing Village1 / 12
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Private Yard
    • Washer
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 25, 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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Duck's Delight - Your Seaside Home Away From Home!1 / 19
    (45)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Grill
    • DVD Player
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    • Porch
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 12, 2017
    We had a wonderful time at duck's delight. The house was great and the ducks even came to visit one morning. It was awesome!!! Thanks so much,The Frey's
    Reviewed September 12, 2017
    This is a truly well kept house with a great location for a terrific price. I will definitely try to rent it every time we go back to Chincoteague.
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    About this property
    Duck's Delight is our home in America's Happiest Seaside Town (2014 Coastal Living)! Entire home updated/renovated for the 2015 booking season! 4 bedroom (3 queen sized beds and 2 sets of bunkbeds), 2 bath Cape Cod in Chincoteague, VA., home of the Assateague ponies. Small fishing town on the...
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    Chincoteague Island, Virginia 23336
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Air Conditioning
    • Housekeeping Included
    • Ocean Views
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    SEA HARBOR: 1 mile from Assateague Island and 5 miles from beach front fun. Check-In 4pm Check-Out 12pm. This home offers large open spaces, a cozy, clean and comfortable place to stay along with amazing adventures for everyone to explore. It is furnished with many necessities so you can rest,...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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
    • Cable/satellite TV
    • Hot Tub
    • Washer
    • DVD Player
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 22, 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 August 31, 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 ! 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
    Rental Home - 2 Bedrooms, 4 Bathrooms, Sleeps 15
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    Tranquil Shores - Relaxation With a Water View1 / 30
    (7)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Grill
    • Waterfront
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    We loved the place as soon as we got there! My mom was given the upstairs room and felt guilty for having the nicest room in the house! We spent most of the daylight hours...
    Reviewed December 5, 2017
    This home was just what we needed for the weekend. It was convenient to get to Main Street for the holiday happenings, stores, and restaurants, as well as convenient to the...
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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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Epiphany on Deep Hole Creek - Waterfront & Dock -wow!1 / 31
    (44)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Ocean Views
    • Patio
    • DVD Player
    • Wi-Fi
    • Waterfront
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 12, 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 August 31, 2015
    And what a week it was. The teens made the most of the clear, sunny days by swinging in the hammock, riding bikes, and kayaking and crabbing (for the first time). The parents...
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    About this property
    Epiphany on Deep Hole Creek. Deep Hole Creek Vacation Rentals Member, Chincoteague Chamber of Commerce Pets subject to approval and an additional fee. See DeepHoleCreek s ite for more info and photos.! Scroll down to email Blair & Martha (owners) . Or Call Blair & Martha at the number listed for...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Terrace
    • Balcony
    • DVD Player
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***7518 Doe Bay Lane***Beautiful waterview 3 bedroom, 2.5 Bath Duplex with waterside balcony, fully equipped kitchen, comfortably furnished.***Bed Sizes: 2 Queen, 2 Twin, 1 Queen Sleep Sofa ***Prime Season Rates: $1195 weekly/$239 per night.Off Season Rates: $775 weekly/$155 per night.Shoulder...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
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    ***7175 Bunting Road*** Totally upgraded townhome with large back enclosed sun porch. Nice wetland view! 2 Bedrooms and 2 baths upstairs. Has Wi-Fi.*** Bed Sizes: 1 King, 1 Queen, 1 Queen Sleep Sofa, 1 Twin Rollaway, 1 Twin Sleep Sofa.*** Prime Season Only: $725 weekly/$145 per night. Additional...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***7141 Wayne Road*** Welcome to Blue Pearl Cottage, a lovely, sunny beach house, just minutes from fabulous beaches, wildlife and the quaint downtown of Chincoteague. This airy cottage nestled beside pine woods has a large wrap-around deck, a screened porch and offers privacy and quiet, with all...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Hidden Treasure1 / 31
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 25, 2016
    We stayed here a few weeks ago. We had stayed in another house on the same street in a previous year- have been coming to the island for decades! The AC is COLD, the deck...
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    About this property
    Escape to the beach - come to this wonderful home nestled within one of Chincoteague Island's most prestigious communities. Hidden Treasure features a great open floor plan downstairs, as well as the privacy of a separate den (with sleep sofa), full bathroom and bedroom (2 twins). A full wall of...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Pet friendly
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    About this property
    ***6422 Church Street*** Enjoy all that downtown has to offer in this cozy island home within walking distance to shops and restaurants. There is plenty of privacy in this petite home! First floor bedroom features a table and Tv, great for hanging out playing games or watching movies while others...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    Waterfront, 5 BR, 4 BA, Elevator, sleeps 101 / 48
    (1)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
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    • Waterfront
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 12, 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
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This property has a location that is rich with amenities. Situated right next to Memorial Park, you can sit on the deck and enjoy the water views as the kids run, play, skateboard, fish and crab. The first floor is an open room consisting of the kitchen, dining area and living room (with queen...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    ***5433 Pearl Drive-Oyster Bay I***Lovely & comfortable 3 bedroom home, newly renovated has sweeping views throughout. Large waterfront screened porch to the back overlooks canal and boat dock. Nicely furnished, wifi, & fully equipped kitchen with granite counter tops. Located in a quiet...
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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Located on the southern end of the island, Family Affair is a town home with gorgeous views of tidal canal in the backyard easily viewed from both stories, including the spacious second-level balcony. Enjoy the water access (tidal canal) and surround yourself in nature from the shared pier, just...
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    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    Anchor’s Rest—Centrally located, just a short walk to the carnival grounds, shopping, ice cream, dinner and the movies. This welcoming, spacious rental home features a fully equipped kitchen (don’t forget to bring k-cups!) with abundant counter space opening into the separate dining room. Enjoy the...
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    Chincoteague Island, Virginia 23336
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    ****5303 Meadow Drive****Well appointed rancher in Piney Island, with large screened porch and private den with sleep sofa. Offers 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 Queen Sleep...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Lighthouse Estates #31 / 22
    (2)Excellent
    2 Bedrooms, 2 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 September 14, 2017
    The location was great, watching the lighthouse at night was amazing. The pool was wonderful to have and well cared for.
    Reviewed June 28, 2016
    Loved everything about this place! Location was perfect to Assateague Island and town. Our 13 year old twin grandchildren loved having big (queen-sizes) beds and own full...
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    About this property
    This comfortable, family friendly vacation rental is waiting for you to enjoy. This unit has pool access and dock access directly across the street for easy access for those fun family fishing and crabbing experiences. It is just a short distance to Memorial Park and Etta's Waterfront dining. The...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***6321 Captain's Lane Unit #320 Sunset Bay Villas*** Luxury Waterfront Condo will delight you with it's vast waterfront views and stylish décor. Overlooking the channel and also offering expansive views of the quaint town of Chincoteague Island. Lovely 3rd floor unit with waterviews from every...
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    Location Information
    Chincoteague Island, Virginia 23336
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sunset Bay Villa 1091 / 20
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 17, 2015
    Rental is clean and spacious. Had an absolutely lovely family vacation and no regrets on splurging on this condo! Condo is well equipped with up to date appliances, and staying...
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    About this property
    This beautiful ground-level villa boasts five-star amenities including a private deck off the living room area with a walk-out to the marina. Enjoy this master bedroom suite, with private bath that features a jetted tub to relax in and a private exit to the waterside deck area. The gourmet kitchen...
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    Location Information
    Chincoteague Island, Virginia 23336
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Cedar Cove1 / 25
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Grill
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    • Waterfront
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    Pet friendly
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    Smoking allowed
    Reviewed September 16, 2017
    Great home for our large family. Quiet location within a bike ride of everything Chincoteague has to offer. Would definitely book again.
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    About this property
    Beautiful custom waterfront home in Oyster Bay. The open floor plan is bright and airy with plenty of room for everyone. The downstairs features an open living & dining room w/ gas fireplace, kitchen, and the master bedroom and bathroom. Upstairs you'll find the other 2 bedrooms and bathroom, as...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Comfortable, pet friendly home on large, side-creek lot with fantastic views from both the front and back of house! Excellent crabbing from dock! (Property sits on creek only suitable for kayaks, canoes and crabbing.) Just a short distance to Memorial Park and Fairgrounds. 2 living room areas, 2...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Terrace
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    Pet friendly
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    About this property
    ***8172 Marsh Point Lane***Charming, traditional island home near town. Walking distance to shops, restaurants, waterfront. Perfect for gathering family/friends. 1 bedroom and 1 bath downstairs/2 bedrooms and 1 bath upstairs.***Bed Sizes: 2 Queen, 1 Queen Sleep Sofa, 2 Twin***Prime Season Rates:...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Panorama1 / 21
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed April 8, 2012
    My husband and I had a wonderful weekend on Chincoteague staying in Panorama. We have stayed many places on the island over the years, and this was just fantastic. Right...
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    Tastefully appointed first-floor condo situated on the Assateague Channel. Enjoy the unobstructed views of the channel and Assateague Lighthouse! Master bedroom suite with doors to waterside deck area, screened porch, open floor plan and more. Recently updated and refreshed, this is a great unit!...
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    Chincoteague Island, Virginia 23336
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Island Retreat1 / 11
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed August 24, 2017
    I enjoyed the stay here with my husband and two daughters. the master was very nice and spacious, i loved the layout and having the kids on 1st floor. Location was very...
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    ***7071 Bond Street***Tastefully decorated townhouse with many new appliances, screen porch and convenient in town location. Offers Wi-Fi. 2 bedrooms and 1 bath downstairs/1 bedroom and 1 bath upstairs.***Bed Sizes: 1 King, 1 Double, 2 Twin, 1 Queen Sleep Sofa***Prime Season Rates: $650 weekly/$130...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    ***3196 Main Street***Enjoy sunsets from this lovely waterfront home with dock!! Offers wireless internet and great views.***Bed Sizes: 1 Queen, 1 Double, 2 Twin, 1 Queen Sleep Sofa***Prime Season Rates: $1100 weekly/$220 per night.Off Season Rates: $800 weekly/$160 per night.Shoulder Season Rates:...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Admiral Benbow1 / 10
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Reviewed August 30, 2013
    My favorite vacation home ever! This house was beautiful and you get that "beach feeling" as soon as you pull in. The bay is within view from the house and the beach is...
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    A very nice contemporary home located in Oyster Bay I. Located next to the community boat ramp - you have access to the water and the kids can fish and crab from the dock areas. This house has an outdoor ramp to the ground level. Don't miss out on the great screened porch for a family dinner. Bed...
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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Shear Water1 / 12
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    ***6347 Jester Street***Unique Pet Friendly Chincoteague home located in town within walking distance to shops and restaurants. Has large fenced in back yard and a private outside rinse area.******New HVAC-Central heating and Air for 2018***Bed Sizes: 1 King, 2 Twins, 1 Daybed with Trundle***Prime...
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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    ***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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    ***4446 Main Street**** Pet Friendly. Proud traditional with a water view of the Chincoteague Bay. Large appointed rooms, back deck and front screened porch.*** Bed Sizes: 2 Queen, 2 Twin, 1 Double*** Prime Season Rates: $875 weekly/$175 per night. Off Season Rates: $650 weekly/$130 per night....
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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    ***5454 Amrien Circle*** Enjoy marsh and bay views from the wrap around deck and screened porch. This bright and cheerful single story home was newly furnished in 2005. Tucked away in a private subdivision off North Main Street. Wi-Fi available. All bedrooms on the same level. Next door to...
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    Chincoteague Island, Virginia 23336
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    ***4274 Pension Street***Quaint cottage near town. Big surprise when you walk inside! Bright, airy kitchen with a separate dining room and spacious living room. Lovely screened side porch and open back yard. Within walking distance to shops, restaurants and waterfront. 2 bedrooms and 2 bathrooms...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    ***3189 Ridge Road**** Lovely island home in great condition. Nice large back yard for the kids. Charcoal barbeque grill and close to Memorial Park and boat launch. 1 bedroom 1st floor/1 bedroom 2nd floor.*** Bed Sizes: 1 Queen, 1 Bunk Bed (1 Twin & 1 Double Futon). 1 Double Futon*** Prime...
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    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    ***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.Shoulder Season Rates: $475 weekly/$95 per night....
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    Location Information
    Chincoteague Island, Virginia 23336
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Luxury waterfront home in Salt Marsh Landing. Spectacular sunsets. A long, private pier over the salt marsh leads you to a bay front dock area with shade. It's perfect for crabbing, fishing or canoe and kayak launching. Well appointed and architecturally pleasing, Castlebar features a main level...
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    Chincoteague Island, Virginia 23336
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    ***Eastwinds 4432***This comfortable townhouse is a great value! It offers two screened porches and spacious rooms.*** Bed Sizes: 1 King, 1 Queen, 1 Twin, 1 Double Sleep Sofa.*** Prime Season Rates: $800 weekly/$160 per night.Off Season Rates: $700 weekly/$140 per night. Additional amenities...
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    Location Information
    Chincoteague Island, Virginia 23336
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 7
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    Charlotte's Morning Sun1 / 26
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Set in the boutique residential community of Oyster Bay II, ‘Charlotte's Morning Sun’ is a stunning 5-star waterfront home that offers unobstructed water views and breathtaking vistas of Oyster Bay. Flowing generously over two levels, Charlotte features 4.5 bathrooms and 4 light-filled bedrooms,...
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    Chincoteague Island, Virginia 23336
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Assateague Breeze1 / 17
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Reviewed May 5, 2017
    We loved this location. Large deck with beautiful views of the bay. We had our own kayaks and used the nearby water access area to go out which was convenient. The master...
    Reviewed June 16, 2015
    We stayed in this house the first week of June and were very pleased with it. We are a family of 6 and had plenty of space. The house has awesome views of the bay and the marsh...
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    ****5466 Amrien Circle****You won't believe the outstanding views of Assateague Island with this lovely 3 Bedrooms, 2 Bathrooms, contemporary home. Lovely marsh to the back, this home has location going on. Large, open and bright great room leads out to deck and porch. Living room with gas...
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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sunset Bay Villas Chincoteague Island - Sunset in Paradise1 / 24
    (7)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
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    Pet friendly
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    Reviewed February 26, 2018
    We stayed in Sunset in Paradise for a week a few years ago and absolutely loved it (and rented again for summer 2018)! The owners are very responsive, hospitable, and helpful in...
    Reviewed February 9, 2018
    Another wonderful week – our second time here in this condo! We came for a relaxing getaway, and it was a successful week. We went on a Saltwater Pony Cruise (our second), did...
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    BEAUTIFUL BAY FRONT CONDO WITH AMAZING WATER VIEWS Owner operated by: Annie Switzer Call 240/498/0074 *** Booking Summer 2018 *** Unit 213 - 'Sunset in Paradise' at Sunset Bay Villas *** Please see VHR 238542 or FKN 7097918 *** *** 'Another Day in Paradise' for our 1st floor unit *** Sunset...
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    Chincoteague Island, Virginia 23336
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    The Bonnie Blue1 / 8
    (1)Terrible
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    ***7065 Wayne Road***Spacious rancher is pet friendly with large deck, fenced yard and internet.***Bed Sizes: 1 Queen, 1 Double, 1 Twin, 1 Double Sleep Sofa***Prime Season Rates: $800 weekly/$160 per night.Off Season Rates: $650 weekly/$130 per night.Shoulder Season Rates: $725 weekly/$145 per...
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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    ***3241 Lekites Drive*** Lovely, spacious home tucked away off Main Street with large deck and 15 by 30 ft pool. 3 bedrooms and 2 baths upstairs (includes master bed and bath), 1/2 bath downstairs. Has WiFi*** Bed Sizes: 2 Queen, 1 Bunk*** Prime Season Rates: $1400 weekly/$280 per night. Off...
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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    ***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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    Chincoteague Island, Virginia 23336
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    Additional Chincoteague Island Info

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    Island vacation rentals - seaside villas, waterfront homes and condos

    Browse through our vacation home rentals, and you’ll discover some very tempting choices for your family vacation. 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 vacation 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 vacation home, if you want to skip the kitchen duties and enjoy their excellent dinner selections.

    Villa and home rentals – the perfect seashore vacation choice

    There is no better way to enjoy a lazy, leisurely island vacation 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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