All Vacation Rentals - MD & VA

The Best Selection of Vacation Rentals from Chincoteague to Ocean City! From Chincoteague, Virginia to Ocean City, Maryland, Seaside Vacations has an unmatched selection of Vacation Homes and Condos to suit your rental needs. From Luxury Oceanfront to serene Bay Views, and everything in between, make Seaside Vacations your one-stop source for your Vacation Rental needs. No one will work harder to provide you with your dream vacation! If you're looking for Navy Housing or other intermediate type stays for work around Wallops Island Flight Facility, give us a call - we can help!

Chincoteague Vacation Rentals

Ready for a Vacation you won't forget? Chincoteague Island has been voted "Best Small Beach Town" & "Happiest Seaside Town." We call it pure paradise! Seaside Vacations has so many beautiful Vacation Homes on the Island - whether you're looking for a Waterfront Dream Home or a Quaint Cottage, we have the perfect Home Base for your adventures.

Located on the Eastern Shore of Virginia, Chincoteague is your escape from the large beach resorts. Experience Chincoteague Island and live like a Local in a Home rather than a Hotel. Enjoy walking to restaurants, shopping, or just spend the day on your private boat dock. We even have pet friendly rentals so you can bring everyone, including your pet. Seaside Vacations provides quality properties that will give you and your family a great stay during your Chincoteague Island Vacation.

While you are here, you can enjoy Historic Downtown, take a Boat Tour, frolic on the Beach at Assateague National Seashore, and visit our Famous Wild Ponies at the Chincoteague Wildlife Refuge. Spend the day fishing in Chincoteague Bay or visiting our quaint Shops downtown. There is so much to do, you won't know where to begin!

Call us today to book a vacation property for your family, a long weekend getaway, or a family reunion. Whatever your needs in a rental property may be, Seaside Vacations is here to assist you.

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Greenbackville, VA
  • 10 Guests
  • 4 Bedrooms
  • 2.5 Bathrooms
  • Code: Aqua Vista
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Chincoteague Island, VA
  • 10 Guests
  • 5 Bedrooms
  • 5 Bathrooms
  • Code: The Inn at Poplar Corner
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Chincoteague Island, VA
  • 8 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Island View
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Chincoteague Island, VA
  • 8 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Angel`s View
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Chincoteague Island, VA
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathrooms
  • Code: The C-Ray Cottage
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Chincoteague Island, VA
  • 7 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: Epiphany
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Greenbackville, VA
  • 10 Guests
  • 4 Bedrooms
  • 4 Bathrooms
  • Code: Calypso
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Ocean City, MD
  • 12 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: Meridian 1002W
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Chincoteague Island, VA
  • 4 Guests
  • 1 Bedrooms
  • 1 Bathrooms
  • Code: Cool Shack
  • Pets Allowed
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Greenbackville, VA
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: The Reel Deal
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Ocean City, MD
  • 13 Guests
  • 4 Bedrooms
  • 3.5 Bathrooms
  • Code: Meridian 206 East
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Chincoteague Island, VA
  • 8 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Frankies Place
  • Pets Allowed
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Starting at (USD)

$200.00

Have it all at Mariner's Watch 104!
Ocean City, MD
  • 8 Guests
  • 3 Bedrooms
  • 2.5 Bathrooms
  • Code: Mariners Watch 104
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Ocean City, MD
  • 8 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Captiva Bay 101
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Ocean City, MD
  • 6 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • Code: Ocean Hideaway 110
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Chincoteague Island, VA
  • 2 Guests
  • 1 Bedrooms
  • 1 Bathrooms
  • Code: Lover`s Lane
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Chincoteague Island, VA
  • 12 Guests
  • 5 Bedrooms
  • 3 Bathrooms
  • Code: Sunset Pointe
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Chincoteague Island, VA
  • 7 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Rhythm & Blues
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Ocean City, MD
  • 4 Guests
  • 1 Bedrooms
  • 1 Bathrooms
  • Code: Ponte Vista 410
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Chincoteague Island, VA
  • 8 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Smooth Sailing
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Chincoteague Island, VA
  • 8 Guests
  • 3 Bedrooms
  • 2.5 Bathrooms
  • Code: Endless Summer
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Atlantic, VA
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Blue Heron
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Chincoteague Island, VA
  • 8 Guests
  • 3 Bedrooms
  • 1.5 Bathrooms
  • Code: Wind Rose
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Chincoteague Island, VA
  • 5 Guests
  • 3 Bedrooms
  • 1 Bathrooms
  • Code: Kelly`s Cottage
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