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Search for your perfect rental & book it on-line with your credit card. IT'S THAT EASY!!

IMPORTANT SEARCH GUIDELINES:
1. If searching by Arrival Date, you must enter a Friday, Saturday or Sunday date. Each day will show different results.

2. When selecting your Length of Stay, you must select in increments of 7 nights during the in season (Memorial Day - Labor Day). You may select any length of stay during the off season.

Availability is updated in real-time, so it is the most current information we have. Once you have completed your reservation, a Guest Rental Agreement (signature required) and Reservation Confirmation will be emailed to you. We look forward to hosting your Chincoteague Island vacation!

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  1. Trembling Bay

    Newly Remodeled * Pier * North Main Street

    This beautifully renovated 3 bedroom, 2 bath Chincoteague cottage is nestled along the salt marshes in a natural setting on Chincoteague Bay. A few of the fine features include a private pier, a new kitchen & appliances, waterside screen porch & deck, and private master bedroom suite with a custom-designed luxurious bath. The numerous windows and over-sized sliding doors allow panoramic water views from nearly any spot in the house. The first floor is completely wheelchair accessible and features your main living areas, large master bedroom suite (K) with bathroom, and second full bathroom with shower/tub. Upstairs features the second and third bedrooms (D/2T). If relaxation is what you're seeking, look no further. This quiet, peaceful location at the water's edge will delight the senses. Come and see for yourself; you won't be disappointed! Read more »
    • Chincoteague Island
    • North Main
    • Single Residence
    • Sleeps 6
    • 3 beds, 2 bathrooms
    • View Details
    Trembling Bay
    5181 Sturgis Lane
    Chincoteague Island VA
    37.9487352, -75.3568125
  2. Blue Heron

    Plenty of space and water access!

    This modern beach retreat features an open floor plan, perfect for socializing with friends or just relaxing after a fun day at the beach. It is located on Oak Drive on Piney Island, closest neighborhood to the beach and convenient for shopping and dining on Maddox Blvd. A few of the amenities include a flat screen TV with cable, wireless internet, and stainless steel appliances in the kitchen. First level includes a master bedroom with a queen bed, a 2nd bedroom with two twins, and 1.5 bathrooms. On the second level you'll find a bathroom with a walk in shower, one bedroom with two double beds and a fourth bedroom with a queen bed. Screened porch (12' x 15') off the kitchen! Your rental also includes community-shared water access to a tidal creek that comes up from Oyster Bay. Note: The water access is shared with the community and is a short distance from the home. Read more »
    • Chincoteague Island
    • Piney Island
    • Single Residence
    • Sleeps 10
    • 4 beds, 2.5 bathrooms
    • View Details
    Blue Heron
    5378 Oak Drive
    Chincoteague Island VA
    37.9263688, -75.3480974
  3. Water's Edge

    Newly Remodeled and Fabulous!

    Water's Edge is an adorable Bay Front cottage in walking distance to Chincoteague's Historic Downtown. You'll be impressed by the charm of this home from the time you pull in the driveway. On the first floor you'll find a full bathroom with an open great room with expansive bay views. There is a large screened porch that leads to an open sundeck that is extended by a private deep water pier with a floating dock. The second level offers two bedrooms and one full bathroom. The master bedroom has a queen bed, private balcony and tower room with panoramic views. The second bedroom offers two bunk beds. Off of the hall is a large second level deck with breathtaking Sunset Views of the Chincoteague Bay. Don't miss the opportunity to book this little slice of heaven... (Note: Woodstove is not usable.) Read more »
    • Chincoteague Island
    • North Main
    • Single Residence
    • Sleeps 7
    • 2 beds, 2 bathrooms
    • View Details
    Water's Edge
    4501 Main Street
    Chincoteague Island VA
    37.9418372, -75.3667824
  4. Nautilus

    Dock with Floating Pier

    All fresh, brand new, and waiting for you! The owners have taken great pleasure and pride in making this fabulous beach home everything that it is today. Enjoy the open floor plan inside that offers water views from nearly every room. There's also a dock with floating pier - perfect for launching kayaks! Come see for yourself! Read more »
    • Chincoteague Island
    • Oyster Bay
    • Single Residence
    • Sleeps 6
    • 3 beds, 2 bathrooms
    • View Details
    Nautilus
    5311 Hibiscus Drive
    Chincoteague Island VA
    37.9455618, -75.3477852
  5. La Dolce Vita

    Private Dock - Bedrooms with Private Baths

    La Dolce Vita = The Sweet Life! Enjoy breathtaking waterfront views and spectacular sunsets from every room in this comfortable luxury waterfront home on Chincoteague Bay! Each of the 4 bedrooms features a private full bath. There are bedrooms on both levels with the master bedroom on the first floor. The MBR suite has a private bath with jacuzzi tub and private waterside balcony. There's also a smaller bedroom with two twins on the first level. The two bedrooms upstairs are private wings off the game room. The game room has two separate gaming tables that young and old alike will enjoy. Checkers with the grandkids! There is bathroom access on this level for guests that use the sleeper sofa in the game room. The kitchen opens to the dining & living room areas which are flanked by floor to ceiling windows & cathedral ceiling. If you're visiting off season, there's a fireplace in the living room for your enjoyment. Off the living room you'll find a large all-weather waterside gazebo that opens out the the decks. It's a perfect spot for your gatherings. La Dolce Vita is a beautiful home with a well-thought-out floor plan that you'll truly enjoy. And the waterfront area has new bulkheading - you can easily crab, fish and launch kayaks from this area. Read more »
    • Chincoteague Island
    • North Main
    • Single Residence
    • Sleeps 10
    • 4 beds, 4 bathrooms
    • View Details
    La Dolce Vita
    5060 Wildcat North
    Chincoteague Island VA
    37.9616149, -75.3383961
  6. Sunset Bay Villa 215

    Beautiful Condo - Elevators, Pool, Fitness Room

    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 tub and tile shower, chef-quality kitchen, pool, fitness room, and large open rooms. Conveniently located to our historic downtown area, you can walk to dinner, movies, shopping, galleries & more. Come and enjoy and great stay at a great place! Note: This property does not have a boat slip. Read more »
    • Chincoteague Island
    • Sunset Bay Villa
    • Condo
    • Sleeps 8
    • 3 beds, 2 bathrooms
    • View Details
    Sunset Bay Villa 215
    6321 Captain's Lane #215
    Chincoteague Island VA
    37.9322012, -75.380982
  7. Sundew

    Popular East Side Location! Fishing/Kayak Pier! Spectacular Views!

    It doesn't get much better than this! Located in one of the East Side's private communities - Fiddler's Bay - this fabulous waterfront retreat is waiting for you. 'Sundew' is nestled on the edge of the natural marshes of the Assateague Channel, lending itself to some of the best wildlife and lighthouse views on the island. This rental includes a community pier that's perfect for launching kayaks or canoes, or for trying your hand at fishing or crabbing. Come and enjoy a relaxing vacation at 'Sundew' - you won't be disappointed! Read more »
    • Chincoteague Island
    • Eastside
    • Townhouse
    • Sleeps 6
    • 2 beds, 2.5 bathrooms
    • View Details
    Sundew
    7186 Fiddler Bay Lane
    Chincoteague Island VA
    37.9224395, -75.3599959
  8. Bay Dreamer

    New Kitchen Renovation & Great Sunsets!

    Bay Dreamer is a spacious 3 bedroom duplex home with multiple porches and decks and spectacular sunset views, just minutes from downtown. When you enter the home you'll find a furnished rec room. The second floor features an open living room (queen sleeper sofa), dining area and kitchen. There is a large screened porch and open deck off of the dining area and another open porch with snipet water views on the front side. You'll also find a 1/2 bath and queen bedroom on the second floor. The third level boasts a master suite with a queen bed and a third bedroom with a bunk bed (Double/Twin). This home may just meet all your vacation needs with central heat and air, ceiling fans, laundry facilities, covered parking, outside shower, grill, DVD, cable TV and wireless internet! Read more »
    • Chincoteague Island
    • North Main
    • Duplex
    • Sleeps 8
    • 3 beds, 2.5 bathrooms
    • View Details
    Bay Dreamer
    5373 Britton Lane
    Chincoteague Island VA
    37.943546, -75.3630289
  9. Island Thyme

    Very Spacious Home Close to Carnival

    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. So come and stay a while; you're on Island Thyme now! Read more »
    • Chincoteague Island
    • In Town
    • Single Residence
    • Sleeps 8
    • 3 beds, 2 bathrooms
    • View Details
    Island Thyme
    7041 Pine Creek Drive
    Chincoteague Island VA
    37.9261265, -75.3826736
  10. Snoozin' Goose

    Fish & Crab From Your Backdoor!

    Beautiful 3 bedroom home located in one of Chincoteague Island's private WATERFRONT communities! Snoozin' Goose offers multiple outdoor porches, an open floor plan with large, bright rooms and modern amenities -- all in a quiet, peaceful location. Enjoy wonderful water views while sitting directly on a canal leading out to Oyster Bay. Tastefully decorated, and you can bring your dog along also! Read more »
    • Chincoteague Island
    • Oyster Bay
    • Single Residence
    • Sleeps 8
    • 3 beds, 2 bathrooms
    • View Details
    Snoozin' Goose
    5412 Coral Court
    Chincoteague Island VA
    37.9423019, -75.347398
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800-668-7836 | rentals@chincoteagueresort.com | http://www.chincoteagueresort.com | 6426 Maddox Blvd, Chincoteague Island, VA 23336