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

Join us for the vacation you will not forget with a vacation from Seaside Vacation rentals. Chincoteague Island has been voted "Best Small Beach Town" & "Happiest Seaside Town". We call it pure paradise and the perfect island getaway!

Seaside Vacations has so many beautiful vacation homes on Chincoteague Island, VA. Our Chincoteague rentals contain a large selection of waterfront, water view, pet friendly, and rentals with pool access. All rental properties are fully furnished and filled with the amenities that will make any family vacation memorable. Enjoy the views of Chincoteague in an amazing vacation home just for you and your family.

Conveniently 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. Most properties are located near downtown Chincoteague, perfect walking distance to restaurants, and shopping. Or just spend the day on your private boat dock. Plan a family friendly vacation with our wide selection of vacation rentals; including with your pet in our pet-friendly rentals.

You can enjoy Historic Downtown, take a Boat Tour, or frolic on the Beach at Assateague National Seashore. Visit Assateague Island, home of the famous wild Chincoteague ponies at the Chincoteague National 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 Chincoteague Island vacation rental 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.

Welcome to Seaside Vacations!

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Chincoteague Island, VA
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Sunset Foals
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Greenbackville, VA
  • 10 Guests
  • 4 Bedrooms
  • 2.5 Bathrooms
  • Code: Aqua Vista
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Chincoteague Island, VA
  • 8 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: Ocean East #1
  • Pets Allowed
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Chincoteague Island, VA
  • 8 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Slack Tide
  • Pets Allowed
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Chincoteague Island, VA
  • 6 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • Code: Pinewood 1A
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Chincoteague Island, VA
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathrooms
  • Code: The C-Ray Cottage
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Ocean City, MD
  • 6 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • Code: Capri 1303
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Chincoteague Island, VA
  • 8 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Smooth Sailing
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Chincoteague Island, VA
  • 2 Guests
  • 1 Bedrooms
  • 1 Bathrooms
  • Code: Assateague Inn 200R
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Ocean City, MD
  • 9 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: Avalon 304
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Chincoteague Island, VA
  • 6 Guests
  • 2 Bedrooms
  • 1 Bathrooms
  • Code: Sandpiper Cottage
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Ocean City, MD
  • 8 Guests
  • 3 Bedrooms
  • 2.5 Bathrooms
  • Code: Sunset Beach 301
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Chincoteague Island, VA
  • 8 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Capt Freeland
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Chincoteague Island, VA
  • 6 Guests
  • 2 Bedrooms
  • 1 Bathrooms
  • Code: Sand Dollar Cottage North
  • Pets Allowed
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Ocean City, MD
  • 7 Guests
  • 1 Bedrooms
  • 2 Bathrooms
  • Code: Summer View 304
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Chincoteague Island, VA
  • 8 Guests
  • 3 Bedrooms
  • 2.5 Bathrooms
  • Code: Ariel`s Grotto
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Chincoteague Island, VA
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Les Bon Temps
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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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Chincoteague Island, VA
  • 8 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Beach Blessing
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Chincoteague Island, VA
  • 8 Guests
  • 3 Bedrooms
  • 1.5 Bathrooms
  • Code: Wind Rose
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Chincoteague Island, VA
  • 8 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • Code: Sunset Bay Villa 221 - Bay Seasoning!
  • Pets Allowed
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Ocean City, MD
  • 13 Guests
  • 4 Bedrooms
  • 3.5 Bathrooms
  • Code: Meridian 206 East
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