Chincoteague Vacation Communities

Seaside Vacations has many wonderful vacation rentals nestled in both large & small communities in Chincoteague Island, VA. Many of our Guests have fallen in love with a certain area or building, and return year after year. We've built "Communities" just for you - to make finding your favorite vacation home just a bit easier!

Check out the Captain's Cove & Yacht Club, filled with amenities that include a Championship 9 hole golf course, 3 Swimming Pools, a Fitness Center, and more. Or maybe you are looking for someplace close to the famous Pony Swim, then Pointer Lane is your place.

Traveling with several families or a large group? Searching our "Communities" page is a great way to find homes that are very close together. If you need any guidance, we are always here, and love helping you find the perfect place to make your vacation memories.

Captains Cove & Yacht Club

Captain's Cove is a wonderful water-privileged community nestled on the shores of Chincoteague Bay. Featuring a championship 9 hole Golf Course, 3 Swimming Pools, Fitness Center, Marina, Full Servi...

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Eagle Sound Estates

Eagle Sound Estates is a gorgeous Community located on the Chincoteague Bay. Only minutes to Chincoteague Island, you'll love this serene, private Paradise that is close to everywhere you want to b...

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Piney Island

Desirable Piney Island is the closest Community to Assateague National Seashore. Ride your bike to the Beach, Dining, Activities, & more! You'll love returning to this tranquil Waterfront Commu...

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Pointer Lane

Pointer Lane is located on the East Side of Chincoteague Island, facing the Chincoteague Channel and Assateague Lighthouse. Many prefer this side of the island, which is also close to where the Pon...

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Steves Cottages

Steve's Cottages are located in the very heart of Chincoteague Island. Tucked away on a quiet street, yet still close to everywhere you want to be - stroll to the Historic District on Main Street t...

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Sunset Bay Villas

Sunset Bay Villas is located directly on the Chincoteague Bay facing the most amazing Sunsets. These Luxury Condos are all Waterfront, and guests enjoy the Community Pool, Hot Tub, and Fitness Cent...

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Teal Lane

Teal Lane is conveniently located just off of Maddox Boulevard, in the heart of Chincoteague Island. From these Homes, you can walk to Amusements, Mini-Golf, Dining, Shops, and more! We have 5 wond...

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The Assateague Inn

Assateague Inn is located on picturesque Chincoteague Island, VA world famous for its "wild ponies" and the annual "pony swim and auction." Just minutes away from the Inn, at biking or dedicated wa...

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Chincoteague Island, VA
Chincoteague Island, VA

Find the Chincoteague Vacation Home of your Dreams right here!

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Ocean CIty, MD
Ocean CIty, MD

Love the action of OCMD? Check out these fabulous Homes!

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Vacation Rental Management
Vacation Rental Management

Are you a Homeowner looking for THE best Property Management Services? Let us show you how we are...

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Real Estate Sales
Real Estate Sales

Been Dreaming of owning a piece of Paradise? You've come to the right place!

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Long Term Rentals
Long Term Rentals

Looking for a Long Term Rental? Let us help you find just the right place!

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