WELCOME TO OUR ON-LINE AVAILABILITY & BOOKING SERVICE!

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. Piney Sands

    Game Room and Great Screened Porches

    Beautiful 3 Bedroom, 2 bath single family home located in Piney Island - the closest community to the beach! Downstairs you'll find an open kitchen and dining area, living room, 2 bedrooms (with twin beds), a bathroom, and a large screen porch. Perfect for enjoying meals outside in the breeze! The upstairs features a master bedroom suite with bathroom, second level screen porch and deck, and game room with ping pong table. Come and check it out! Read more »
    • Chincoteague Island
    • Piney Island
    • Single Residence
    • Sleeps 8
    • 3 beds, 2 bathrooms
    • View Details
    Piney Sands
    5408 Oak Drive
    Chincoteague Island VA
    37.9269596, -75.3457423
  2. Cowboy Cottage

    Popular Rental * Pet Friendly

    Cowboy Cottage is a pet friendly home conveniently located a block from Maddox Blvd., and just a couple of blocks from downtown Main Street. This ranch-style home has an open floor plan and is handicap accessible with a ramp to enter the house and bedroom/bathroom accessibility. There is a large screened porch and a fenced in yard that is divided - one side is for your furry family members to run and in the second section there is a swing set and area for the kids. Book this one today! Read more »
    • Chincoteague Island
    • In Town
    • Single Residence
    • Sleeps 6
    • 3 beds, 2 bathrooms
    • View Details
    Cowboy Cottage
    6345 Clark Street
    Chincoteague Island VA
    37.9329181, -75.3680853
  3. A Sunshine Cottage

    Charming Chincoteague-Close to Downtown

    As one of our newest vacation rental listings, we're pleased to be able to offer you "A Sunshine Cottage"! With all the charm of a Chincoteague-style cottage, you'll be reminded of the days gone by. The front porch is the perfect spot to relax with a cool drink and book, and the convenient in-town location means you can stroll downtown after a day at the beach. Read more »
    • Chincoteague Island
    • In Town
    • Single Residence
    • Sleeps 4
    • 2 beds, 1 bathrooms
    • View Details
    A Sunshine Cottage
    6336 Jester Street
    Chincoteague Island VA
    37.9314724, -75.3795889
  4. Diving Duck

    Golf * Swimming * Tennis * Fine Dining

    If you're looking for the complete vacation package, look no further! This newly renovated 4 bedroom home features a spacious open floor plan with wall-to-wall sliding doors and windows, allowing natural light to permeate throughout the home. Downstairs you'll find the living room and great room with access to the waterside deck, a large dining area, kitchen with all the counter space you'd ever need, a half bathroom, and the master bedroom with private bath (with custom tile shower and soaking tub). Upstairs features a landing area with sofa and foosball table, 3 more bedrooms and another full bathroom. Under the house, you'll find the perfect spot for a game of ping pong. Aptly named, 'Diving Duck' is the perfect spot for watching the ducks and wildlife pitch in the bay just out the back door. There's even a floating dock perfect for launching canoes and kayaks! And as if all of that is not enough, the Captains Cove community features swimming pools (2 outdoor, 1 indoor), a fitness center, marina club restaurant and 9-hole golf course. It is approximately 20 minutes to Chincoteague/Assateague Island (the beach) and 30 minutes to Ocean City, MD (beach & boardwalk attractions). What more could you ask for? Book your stay at 'Diving Duck' today! NOTE: The use of the pools and golf facilities requires a small additional fee. Read more »
    • Captains Cove
    • Captains Cove
    • Single Residence
    • Sleeps 15
    • 4 beds, 2.5 bathrooms
    • View Details
    Diving Duck
    3224 Salty Way
    Greenbackville VA
    37.9901597, -75.4154453
  5. 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
  6. Holly Haven

    • Chincoteague Island
    • In Town
    • Single Residence
    • Sleeps 10
    • 3 beds, 2 bathrooms
    • View Details
    Holly Haven
    6494 Holly Drive
    Chincoteague Island VA
    37.9269013, -75.3711402
  7. Snowy Egret

    Room for the Whole Gang - Crabbing

    Light, bright & airy, Snowy Egret is a wonderfully large vacation home that boasts a full ensemble of amenities along with a nice waterfront setting. Downstairs you'll find a large living/dining room combo and a nice modern kitchen. Off the kitchen is a private den area (futon) - a perfect spot to catch up on your reading! There's a half bath on the first floor. All bedrooms are on the second level. There's a master bedroom suite as well as another full bath on the second level. Snowy Egret features central heat and air, laundry facilities, garage and more. Located on a bulkheaded lot on a canal that comes up from Oyster Bay, you can through your crab pot in right outside the back door. Please note: House is dog-friendly only, no cats. Read more »
    • Chincoteague Island
    • North Main
    • Single Residence
    • Sleeps 11
    • 4 beds, 2.5 bathrooms
    • View Details
    Snowy Egret
    5065 Twilley Drive
    Chincoteague Island VA
    37.9506003, -75.3439689
  8. Footprints In The Sand

    Water Access - Bring Your Kayak!

    This great 3BR/2.5BA home is located on Piney Island, our closest residential community to Assateague. Walk or bike to Assateague! Amenities include central air, large screened porch, open floor plan with nice kitchen and bedrooms on both levels. There's a fireplace for our fall guests. Spacious & accommodating, this is a great vacation rental home. Your rental also includes water access to a creek that comes up from Oyster Bay - it's a great place for the kids to crab or to launch a kayak or canoe. Note: Water access is shared with the community and is a short distance from the property. Read more »
    • Chincoteague Island
    • Piney Island
    • Single Residence
    • Sleeps 8
    • 3 beds, 2.5 bathrooms
    • View Details
    Footprints In The Sand
    5388 Oak Drive
    Chincoteague Island VA
    37.9265823, -75.3472544
  9. Mallard's Walk

    Great Home Bring Your Kayak

    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 No pets. Wireless Internet and a fully enclosed outside shower with foot wash! NOTE: This rental features a large front yard, and the dock/waterfront access is across Eastside Road. Private pier. Read more »
    • Chincoteague Island
    • Eastside
    • Single Residence
    • Sleeps 6
    • 3 beds, 1 bathrooms
    • View Details
    Mallard's Walk
    7259 Mcgee Lane
    Chincoteague Island VA
    37.9194005, -75.3705005
  10. Southern Dream

    Quiet Location and Nice Water Views

    Charming 3 bedroom ranch home located in one of Chincoteague Island's finer residential communities. Nice, quiet location with a water view of Oyster Bay. Spend your time outside on the spacious deck or screened porch - there's plenty of room for all! Many modern amenities such as central air, high speed internet, charcoal grill and an outside shower will ensure your comfort during your stay! Read more »
    • Chincoteague Island
    • North Main
    • Single Residence
    • Sleeps 8
    • 3 beds, 2 bathrooms
    • View Details
    Southern Dream
    5521 Amrien Circle Drive
    Chincoteague Island VA
    37.935305, -75.355246
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800-668-7836 | rentals@chincoteagueresort.com | http://www.chincoteagueresort.com | 6426 Maddox Blvd, Chincoteague Island, VA 23336