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Vacation Rentals near Captain Jay's Adventures - Private Tours

2246 Curtis Merritt Harbor Drive., Slip 22, Chincoteague Island, Virginia 23336
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    Travelers to Chincoteague Island are booking April dates now. Secure your vacation rental today, and have the perfect trip.
    All 100 Rentals in Chincoteague Island
    Sea Heart & Soul, Waterfront Memorial Park Rental1 / 32
    (11)Excellent
    1.7 miles from Captain Jay's Adventures - Private Tours
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Sea Adventure: Waterfront  Views, Pier at this Park Rental!!!1 / 19
    (2)Excellent
    1.7 miles from Captain Jay's Adventures - Private Tours
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Spacious, historic Chincoteague Is. vacation house1 / 13
    (12)Very good
    1.8 miles from Captain Jay's Adventures - Private Tours
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Cozy cottage near Old town Fishing Village1 / 12
    (2)Very good
    2.4 miles from Captain Jay's Adventures - Private Tours
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Private Yard
    • Washer
    • Parking
    • 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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    Chincoteague Island, Virginia
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Beautiful Chincoteague Island retreat1 / 15
    (18)Very good
    2.3 miles from Captain Jay's Adventures - Private Tours
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Porch
    • DVD Player
    • Parking
    • Washer
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Cute little neighborhood off Main Street. It's an easy walk to the shops and restaurants downtown. Of course, the main attraction for us is always the beach at Assateague. We...
    Reviewed September 4, 2018
    Nice location walking distance to town and to the pier for fishing. Located on a quiet street. House was cozy and decorated nicely.
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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
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Dancing Water View1 / 9
    (2)Excellent
    1.9 miles from Captain Jay's Adventures - Private Tours
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 23, 2018
    This place is spectacular- already discussing another visit! Thank you!! Very clean, dock was great, nice breeze nightly. Central to everything.
    Reviewed April 9, 2018
    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
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    Assateague Light1 / 11
    (1)Very good
    2.1 miles from Captain Jay's Adventures - Private Tours
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 25, 2012
    Assateague Light is a very nice first-floor waterfront condo facing the Assateague Channel. The view from the deck is spectacular. When we were looking for vacation rentals on...
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    About this property
    This modern 2 bedroom condo located on the first floor features a master bedroom suite with a king bed, private bath and sliding glass door to the waterfront deck. The second bedroom has two twin beds with a full bathroom across the hall. This shared bath offers a walk in shower and washer/dryer....
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    Location Information
    Chincoteague Island, Virginia
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2.1 miles from Captain Jay's Adventures - Private Tours
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Aptly named, you'll enjoy a nice relaxing vacation at 'Tranquil Escape!' As one of the newest additions to the vacation rental market, this home is located in a quiet residential neighborhood and features expansive porches and outdoor areas for you to enjoy! With 4 bedrooms, 3.5 bathrooms, an...
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    Chincoteague Island, Virginia
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Wildflower1 / 34
    (1)Very good
    1.4 miles from Captain Jay's Adventures - Private Tours
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 18, 2018
    Overall this was a really nice place. It is on a quiet street, has a really nice large backyard and private dock. The kids loved playing there and fishing/crabbing from the dock...
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    About this property
    Beautiful waterfront home with shared pier plus floating dock on deep water!! Ground level is a large screened patio perfect for those summer time seafood feasts. The first level is great room boasting reclaimed barn board walls and wide plank pine floors with a separate den and full bath. There is...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Charlotte's Morning Sun1 / 26
    (2)Average
    2.1 miles from Captain Jay's Adventures - Private Tours
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Terrace
    • Waterfront
    • Balcony
    • DVD Player
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Set in the boutique residential community of Oyster Bay II, ‘Charlotte's Morning Sun’ is a stunning 5-star waterfront home that offers unobstructed water views and breathtaking vistas of Oyster Bay. Flowing generously over two levels, Charlotte features 4.5 bathrooms and 4 light-filled bedrooms,...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Daisey Cottage1 / 8
    (1)Excellent
    1.2 miles from Captain Jay's Adventures - Private Tours
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Air Conditioning
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    Pet friendly
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    Smoking allowed
    Reviewed July 21, 2018
    This cottage was adorable and had everything we needed. It made our beach vacation absolutely wonderful! The layout was open and the decor was adorable. The master bedroom...
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    About this property
    Quaint and charming island cottage with all the amenities! Located on the southern end of the island, Daisey Cottage offers everything you'll need for an enjoyable vacation - central a/c, dishwasher, WiFi, washer/dryer and more. And it's even pet friendly! Additional amenities include: 4 pets max....
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    Bayside II1 / 20
    (2)Excellent
    0.9 miles from Captain Jay's Adventures - Private Tours
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • DVD Player
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 1, 2018
    Bayside II had everything you could ask for in a vacation home. Lots of amenities and the small things that make a house a home. Lots of room and open space with the living and...
    Reviewed June 19, 2018
    Our rental home was beautiful ! Well equipped! Clean! We couldn’t have asked for a more perfect place to rent. The process was simpleAnd we’re well tended to by the rental...
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    About this property
    Bayside II is a well appointed, WATER VIEW, 3-bedroom duplex located just off of South Main Street on the quiet southern end of the island. This spacious, nearly 2,000 sq ft. home offers a family of up to 8 an open floor plan with plenty of space to enjoy. The home has 3 decks - 2 facing the...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sunset Bay Villa 1141 / 26
    (1)Excellent
    2.4 miles from Captain Jay's Adventures - Private Tours
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 14, 2014
    The unit we stayed in was beautifully decorated and clean. Being on the first floor, we have easy access to the pool and the marina. Loved that there is an outdoor shower by the...
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    About this property
    Villa 114 is a beautiful, professionally decorated unit located close to the pool and fitness area. Spacious, light and bright, this ground-level unit features a private deck area with walk-out to the marina. The master bedroom has a private luxury bath with jetted tub and tiled shower; the gourmet...
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    Location Information
    Chincoteague Island, Virginia
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sunset Bay Villas - Another Day in Paradise1 / 33
    (10)Excellent
    2.4 miles from Captain Jay's Adventures - Private Tours
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Washer
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 30, 2018
    The location of this condo is amazing. You have gorgeous views of the bay from the living room - dinning room area and the master bedroom. The sunsets were amazing. We liked...
    Reviewed April 2, 2018
    Annie was so helpful & always prompt with answering any questions I had. The condo was very clean, spacious & suited our needs perfectly! The location is awesome being...
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    About this property
    ANOTHER DAY IN PARADISE CHINCOTEAGUE BEAUTIFUL BAY FRONT CONDO WITH AMAZING WATER VIEWS Owner operated by: Annie Switzer Call 240/498/0074 *** Booking Fall 2018 & Beyond *** PLEASE CONTACT ME BEFORE BOOKING SUMMER 2019 Unit 103 - 'Another Day in Paradise' Unit 213 - 'Sunset in Paradise' 2nd...
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    Location Information
    Chincoteague Island, Virginia
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sunset Bay Villa 2061 / 25
    (2)Excellent
    2.4 miles from Captain Jay's Adventures - Private Tours
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 4, 2018
    Beautiful condo! Everything is up to date and clean. Lovely view of the marina. Very conveniently located from town. It’s a couple blocks from Bills Prime. We also walked to the...
    Reviewed July 22, 2018
    We loved Sun Set Bay 206. We've rented other units in the complex, but this was our favorite by far. Everything needed is there. Plenty of seating for everyone. Internet worked...
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    About this property
    Villa 206 is a new unit that has been professionally decorated and offers five-star luxury. Spacious and accommodating, the gourmet kitchen is perfect for cooking your favorite meals. It's well stocked and ready for your handiwork. There are three bedrooms, including a master bedroom suite with...
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    Location Information
    Chincoteague Island, Virginia
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2.4 miles from Captain Jay's Adventures - Private Tours
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on the edge of beautiful Chincoteague Bay, Sunset Bay Villas are distinctive condominium homes that offer nothing less than the finest amenities. This unit boasts over 1,700 square feet of living space with 3 bedrooms (each with own flat-screen TV), spacious waterfront balcony, private...
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    Location Information
    Chincoteague Island, Virginia
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Drop Anchor1 / 18
    (2)Excellent
    0.7 miles from Captain Jay's Adventures - Private Tours
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 15, 2018
    Nice house with all amenities you need available. Location is convenient for putting a boat in at Curtis Merritt Harbor or at other town ramps. Quiet, clean, beautifully...
    Reviewed November 15, 2017
    This place has such a nice flow to it. Everything you need for a relaxing time on the Island. Fishing within walking distance. Loved it, wished I could have stayed...
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    About this property
    Formerly known as 'Dreamweaver', Drop Anchor is a luxury rental nestled on a quiet cul-de-sac beneath the tall pines. All amenities including a great open kitchen, screened porch, wireless internet, gas fireplace and bedrooms on both levels. The upstairs master bedroom suite is spacious and...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Mermaid Crossing1 / 21
    (1)Excellent
    1.8 miles from Captain Jay's Adventures - Private Tours
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 10, 2018
    This location was an unexpected delight! More than any one particular thing, it was comfortable! We will be returning!
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    About this property
    Comfortable, pet friendly home on large, side-creek lot with fantastic views from both the front and back of house! Excellent crabbing from dock! (Property sits on creek only suitable for kayaks, canoes and crabbing.) Just a short distance to Memorial Park and Fairgrounds. 2 living room areas, 2...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    0.6 miles from Captain Jay's Adventures - Private Tours
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Misty's Thicket1 / 16
    (2)Very good
    0.6 miles from Captain Jay's Adventures - Private Tours
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 28, 2017
    Our family's second visit to Misty's Thicket was just as perfect as our first. Very comfortable house and the dock for crabbing is where we spend most of our time. We caught...
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    About this property
    Located on South Ridge Road, this lovely town-home features a private pier, central air conditioning, and galley style kitchen complete with a dining area and all necessary appliances. The cozy living room leads you onto one of two screened in porches perfect for unwinding with family and friends....
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sunset Bay Villa 1091 / 25
    (1)Excellent
    2.4 miles from Captain Jay's Adventures - Private Tours
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
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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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    Chincoteague Island, Virginia
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2.2 miles from Captain Jay's Adventures - Private Tours
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great 2 bedroom, 2.5 bath townhome in Lighthouse Estates community off East Side Drive. This home features all amenities including central air, washer/dryer and new kitchen appliances. In addition, there is a community pool as well as water access and a dock (shared) to fish and crab from. This is...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2.3 miles from Captain Jay's Adventures - Private Tours
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    As a classic Chincoteague-style home, Hopkin's House is situated on the East Side of Chincoteague Island and overlooks the Assateague Channel. You'll enjoy a wonderful, relaxing vacation at this 3 bedroom home; it's just a short distance from the public boat ramp, Memorial Park, a restaurant and...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Serendipity1 / 20
    (2)Very good
    2.2 miles from Captain Jay's Adventures - Private Tours
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come stay in this classic Eastern Shore Style home. Located just a few blocks from our famous downtown Main Street area, you are within walking distance to most of our shops and restaurants. Serendipity has a very nice screened porch for those memorable Chincoteague Summer evenings. This home also...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Paradise1 / 28
    (1)Excellent
    2.0 miles from Captain Jay's Adventures - Private Tours
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 19, 2017
    Beautiful stunning and breath taking ! The view was beautiful. House was clean upon arrival, very spacious! Loved the kitchen. The bedrooms were very clean and spacious! Loved...
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    About this property
    If you're looking for that special vacation home that offers everything you'll need, look no further. Paradise offers all top-of-the-line amenities including cherry wood floors, chef's kitchen and spacious master bedroom suite with custom bathroom and Jacuzzi tub. The main floor features a bright,...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Stingray1 / 15
    (2)Very good
    2.1 miles from Captain Jay's Adventures - Private Tours
    2 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
    Reviewed September 1, 2017
    I can not say enough about the view from this condo. The place was very clean and close to the beach and all of the attractions. The rental was clean and decorated nicely. My...
    Reviewed July 8, 2012
    I recently stayed at the stingray with my husband, our two-year-old son, and my mother who came for a few nights. The condo was well outfitted, comfortable and clean. It was...
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    About this property
    Luxurious 2nd-level waterfront condo with views you won't believe! Tastefully decorated with work of local artisans, features all amenities, as well as master bedroom suite with king bed & waterside balcony. Many extras like a flat screen TV and a Lazy Boy leather recliner. The open floor plan is...
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    Location Information
    Chincoteague Island, Virginia
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1.7 miles from Captain Jay's Adventures - Private Tours
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2.2 miles from Captain Jay's Adventures - Private Tours
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come enjoy this 2-bedroom, 2.5 bath townhouse in the Lighthouse Estates community off East Side Drive. There is a community pool as well as water access and a dock (shared) to fish and crab from. This unit features a washer/dryer, wireless internet, central air conditioning and all the other...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Channel Lookout1 / 13
    (2)Excellent
    1.7 miles from Captain Jay's Adventures - Private Tours
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • DVD Player
    • Grill
    • Air Conditioning
    • Terrace
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 30, 2018
    This house was perfect for our family. It is in a convenient location and the house self is very comfortable.
    Reviewed June 2, 2018
    Nice duplex. All rooms accept bathroom face the Assateague Channel. Very quiet location. Great setup for two friends. One twin headboard needs to be tightened. Ceiling fans in...
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    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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sundance1 / 20
    (3)Excellent
    2.1 miles from Captain Jay's Adventures - Private Tours
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • DVD Player
    • Wi-Fi
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 13, 2017
    Our stay was AMAZING!! Our family of 7 loved everything about this rental! Clean house, more than enough room for all of us, 3 full bathrooms! Quiet, welcoming home! We...
    Reviewed August 1, 2017
    This house is spacious, comfortable, well decorated, and labeled. Yes, labeled! The owner has every switch, cupboard, drawer, and remote labeled, which we really appreciated, as...
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    About this property
    Light, bright and airy - this beautiful home is very well maintained, tastefully furnished and boasts all amenities including screened porch, outside shower, all appliances including washer/dryer, tvs in every bedroom and more. The home is located just outside of town and offers a very quiet...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    Lighthouse Pointe1 / 25
    (2)Excellent
    2.3 miles from Captain Jay's Adventures - Private Tours
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 15, 2018
    Nice location and well laid out house. Enjoyed the daily views and nighttime quietness. Easy checkin/checkout. Will come back again.
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    About this property
    One of East Side's most popular rentals! Features include open floor plan with waterside balcony downstairs, and a spacious third level master bedroom suite with private waterside balcony. All levels have balconies or a deck! Very conveniently located - close to Memorial Park, restaurants and...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Island Thyme1 / 14
    (2)Very good
    2.0 miles from Captain Jay's Adventures - Private Tours
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 23, 2017
    I found the house pleasant and pretty, the decor was all seaside with shells and beach shoes and quiet colours. I was disappointed that there was no wifi, as I had thought I...
    Reviewed July 16, 2013
    I loved this property. This was the third time my family and I stayed at Island Thyme. The location is great, it's in the middle of the little town and less than half a mile...
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    About this property
    There's plenty of room for everyone here at Island Thyme! This spacious home features a living room and den, large eat-in kitchen and dining area, and a huge wrap-around deck -- perfect for enjoying the quiet, peaceful setting. The many extras include a hot tub (on back deck), and Foosball table....
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sunny Shack1 / 32
    (1)Very good
    0.6 miles from Captain Jay's Adventures - Private Tours
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Balcony
    • Terrace
    • Air Conditioning
    • DVD Player
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 28, 2016
    One thing to note, the dock pictured is across the street -- not a terribly busy street -- but still not on property "proper." Our kids loved crabbing and catching...
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    About this property
    Words cannot describe this top-of-the-line luxury townhome. The moment you walk in, you'll find a game room with pool table board games and a large flat screen TV. The second level is a spacious open floor plan with views of the water from just about everywhere. The chef's grade kitchen has...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    On Island Time1 / 20
    (1)Excellent
    2.3 miles from Captain Jay's Adventures - Private Tours
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 29, 2017
    We have been coming to Chincoteague Island since 1988 and this is the best house we have been to. The décor is sweet and thoughtful. All the little touches are lovely and the...
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    About this property
    Wow... What a show piece! 'On Island Time' is exactly what you expect in your beach home, from the bright and fun decor to the spacious and bright floor plans, all of this wrapped in a traditional Eastern Shore Home. The front enclosed porch is great for reading or just relaxing in the afternoon...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Mallard's Walk1 / 25
    (1)Excellent
    2.2 miles from Captain Jay's Adventures - Private Tours
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 14, 2016
    This is the second year we stayed at Mallard's Walk. We have stayed different places over the years, and this is by far our favorite. We love that the dock is across the road...
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    About this property
    Enjoy the wonderful bay breezes from this charming waterfront home. Three bedrooms, great spacious kitchen, quiet porch to relax on and your own private pier/dock on Assateague Channel. Watch our world famous Chincoteague wild ponies grazing in the salt marshes of Assateague Island. No smoking and...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Horseshoe Haven1 / 14
    (1)Very good
    2.3 miles from Captain Jay's Adventures - Private Tours
    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Amenities & Details
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 31, 2018
    Cannot say enough about this wonderful rental & Harbour Realty. House was very clean & well stocked. A great family rental and a plus was being able to bring out pup...
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    About this property
    ***7111 Horseshoe Lane*** Lovely home centrally located on a quiet residential street. Watch the Saltwater Cowboy's saddle up for the pony round ups right from the comfort of the airy screened porch. Too hot at the beach, no problem than enjoy the pool. This home has all the amenities for beach...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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    2.4 miles from Captain Jay's Adventures - Private Tours
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on the edge of beautiful Chincoteague Bay, Sunset Bay Villas are distinctive condominium homes that offer nothing less than the finest amenities. This unit boasts over 1,700 square feet of living space with 3 bedrooms. Spacious waterfront balcony, private master bedroom suite with whirlpool...
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    Location Information
    Chincoteague Island, Virginia
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sea Treasure1 / 12
    (1)Very good
    1.3 miles from Captain Jay's Adventures - Private Tours
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Terrace
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 17, 2017
    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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    About this property
    ***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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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Sunset Bay Villa 1111 / 18
    (2)Excellent
    2.4 miles from Captain Jay's Adventures - Private Tours
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 19, 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 suite has a queen bed with a private bathroom and access to the waterfront deck....
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    Location Information
    Chincoteague Island, Virginia
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Bayside1 / 26
    (5)Very good
    0.9 miles from Captain Jay's Adventures - Private Tours
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 19, 2018
    This was our second year at Bayside and we love it! It’s roomy enough for our whole family, 4 adults, 3 kids and our dog! The pier is amazing, we spent a lot of time out there...
    Reviewed September 19, 2017
    Bayside was one great place to stay! It was clean and comfortable, and the views of the sunset were unbelievable! Extra special because we could bring our pets, who enjoyed...
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    About this property
    Luxury waterfront townhome overlooking Chincoteague Bay. Beautiful sunsets! Long pier for fishing and crabbing. All amenities including all appliances, central air and enclosed porch (with air conditioning). Need more room? Bayside already booked? Try our sister homes right next door, Sunset Dreams...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    SNUG HARBOR WATERFRONT COTTAGE with a stunning view of lighthouse and ponies!1 / 49
    (42)Excellent
    1.9 miles from Captain Jay's Adventures - Private Tours
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Waterfront
    • Outdoor Dining Area
    • Grill
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 21, 2018
    Adorable water front cottages nestled within a cozy neighborhood-- just driving minutes from Main Street, gift shops, restaurants, and the beach. Super laid back! Perfect for a...
    Reviewed July 13, 2018
    The staff are very polite and helpful. The cottages are clean and well maintained. And the view is stunning. It made my vacation very enjoyable!
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    About this property
    It's a celebration of nature in its most magnificent form, as the wild Chincoteague ponies run up and down the marshland, the local birds will sing you a song. As this perfect day comes to an end, the laid back reggae tunes will set the mood for the miraculous montage of Caribbean colors that make...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2.1 miles from Captain Jay's Adventures - Private Tours
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your home away from home... enjoy the water views, bring your boat and use your own dock or just relax and listen to the whispering pines. Great views of Oyster Bay off the front deck. 3 Bedrooms, 2 full baths (plus another shower/bath downstairs), outside shower, washer and dryer, satellite TV,...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Sunset Bay Villa 2091 / 28
    (1)Very good
    2.4 miles from Captain Jay's Adventures - Private Tours
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 15, 2015
    This unit is easily accessible, and nicely decorated. It truly felt like home for a week. Its a short walk to restaurants, shops, and groceries in downtown. Sit on the deck...
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    About this property
    A sense of the tropics! This British Colonial style villa is one of our most popular villas. You can enjoy romantic sunsets on the waterside balcony at the end of the day, or enjoy a soothing soak in a luxury jetted tub located in the master bath. Sunset Bay amenities (outdoor pool, fitness room...
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    Location Information
    Chincoteague Island, Virginia
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sunset Dreams1 / 31
    (1)Excellent
    0.9 miles from Captain Jay's Adventures - Private Tours
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 16, 2018
    Our stay at Sunset Dreams was amazing. This was the second year there, we have been coming to Chincoteaque for 25+ years and this is one of the best. The sunsets from the pier...
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    About this property
    Sunset Dreams is a Luxury Waterfront town-home overlooking Chincoteague Bay, the perfect spot for unwinding while you watch the island’s vivid sunsets. This unit includes a second-floor balcony, water views from almost every room, a large master suite, an enclosed air-conditioned porch, wireless...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2.4 miles from Captain Jay's Adventures - Private Tours
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Terrace
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***FEATURED SPECIAL - DON'T MISS OUT ON THIS SPECTACULAR DEAL! BEAUTIFUL WATERFRONT CONDO FOR $2000 A MONTH SEPTEMBER - NOVEMBER - You can't beat this price! If you are looking for a long stay for fun or coming for work, this condo is perfect! Has everything you need, including linens and...
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    Location Information
    Chincoteague Island, Virginia
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    1.1 miles from Captain Jay's Adventures - Private Tours
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
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    About this property
    ***7514 Beebe Road*** Artist styled bungalow is delightful and comfortable.*** Bed Sizes: 2 Queen, 3 Twin, 1 Sleep Sofa*** Prime Season Rates: $750 weekly/$150 per night. Off Season Rates: $650 weekly/$130 per night. Additional amenities include: internet/wi-fi, outside shower, suitable for...
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    A Shore Thing1 / 22
    (3)Very good
    1.3 miles from Captain Jay's Adventures - Private Tours
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 4, 2016
    We had a great time at the vacation house. The house was as expected and nicely decorated. The beds were a little hard but the view was beautiful and made up for it. We...
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    About this property
    A very nice waterview duplex overlooking Assateague Island and the lighthouse. Located across the street from 'Mr. Baldy's Restaurant' and within walking distance to Memorial Park park (where there is a boat ramp, a fishing pier, and play area for the kids). Enjoy the waterside screened porch....
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    Location Information
    Chincoteague Island, Virginia
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sea Tag #221 / 19
    (1)Very good
    1.9 miles from Captain Jay's Adventures - Private Tours
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • DVD Player
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 12, 2015
    Nicely remodeled 2 BR/1 BA Condo. Great view of Assateague Island & the lighthouse. Perfect for pony penning & bring your binocs to view the ponies year round. Rental...
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    About this property
    We are pleased to be able to offer you this fabulous 2nd level unit! The interior has been completely renovated, from the drywall and paint, to the furniture! You'll enjoy all modern amenities including flat-screen TVs (3), internet, washer/dryer facility and updated kitchen (appliances, cabinets,...
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    Location Information
    Chincoteague Island, Virginia
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Sunset Bay Villa 3161 / 23
    (3)Very good
    2.4 miles from Captain Jay's Adventures - Private Tours
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travelers have booked this property
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 25, 2017
    We spent two weeks here in September, and it was a wonderful stay! The unit is beautifully decorated with gorgeous sunset views from its third floor balcony; and it's in...
    Reviewed March 1, 2017
    We spent a week here in August 2016. Would definitely book again. The unit is on the top floor and the porch has a breeze so we did not see a single mosquito the whole time we...
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    About this property
    This beautiful bayside villa, professionally decorated, features luxury amenities including a walk-out from the living room area to a private deck. The master bedroom suite is a dream come true - beautiful tiled shower, jetted tub and more. The gourmet kitchen will please your senses. This 3...
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    Location Information
    Chincoteague Island, Virginia
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Panorama1 / 21
    (1)Excellent
    2.1 miles from Captain Jay's Adventures - Private Tours
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Wi-Fi
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    About this property
    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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    Location Information
    Chincoteague Island, Virginia
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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