Discover a selection of 4,000 vacation rentals in Assateague Island, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $105 per night, and cabins and houses are popular options for a stay in Assateague Island. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Assateague Island
Destination guide

Assateague Island is where the wild ponies roam

It may be just 8 miles south of Ocean City, but Assateague Island feels worlds away from Maryland's favorite beachside resort. With its secluded beaches and rolling sand dunes, this undeveloped barrier island offers a unique glimpse at untamed America. And of course, no mention of Assateague Island is complete without a nod to its herd of wild ponies, made famous by Marguerite Henry's iconic novel, Misty of Chincoteague. If you're looking for reading material while relaxing on the deck of your Assateague Island vacation rental, why not try this American classic?

Things to do

Beachcombing on Assateague Island

Stretching for 2 miles along the coast, Assateague State Park showcases everything that's great about this whimsical barrier island. The beach is sheltered, which makes it a great place to swim, sunbathe, or unpack a picnic. If you're traveling with a pet, some areas are even dog friendly. Assateague Island vacation rentals make it easy to bring along Fido, with a fantastic lineup of pet-friendly properties. From wild ponies to migratory birds, the Chincoteague National Wildlife Refuge gets you up close and personal with the island's most famous residents.


Discover the Assateague Island seashore

Managed by the government, the Assateague Island National Seashore offers fun for the whole family. Whether you want to cruise along the 4-mile cycling trail, catch a ranger talk, or check out the exhibits at the visitor center, the seashore is made for discovery. Camping is available year-round, but if you'd rather not rough it Assateague Island vacation rentals put you just minutes from the island. Most are located in nearby Chincoteague, a characterful town that serves as the gateway to Assateague Island.


Lazy days in the Assateague sunshine

Summer brings high season in Assateague Island, with warm weather and calm waters that are perfect for unhurried beach days. Chincoteague kicks into full swing vacation mode, with plenty of breezy caf_s, seafood restaurants, and pony-themed gift stores to explore. Every July the island hosts the annual Chincoteague Wild Pony Swim. It's quite the event, with 10s of 1000s of visitors gathering on the seashore to watch the spectacle. Winter feels wild and windswept, and is the perfect time to enjoy a laid-back island escape.

Natural features

Enjoy birdwatching on Assateague Island

Sitting just off the Delmarva Peninsula, Assateague Island is a constantly shifting ribbon of sand, shaped by powerful winds and waves. It backs onto the expanse of the Atlantic Ocean, with a mosaic of salt marshes, sand dunes, and maritime forests making up the interior. Beyond its famous wild ponies, Assateague Island is a bucket list destination for birders. Both resident and migratory birds flock to the 14,000 acre Chincoteague National Wildlife Refuge, where you can spot piping plovers, great blue herons, ruby-crowned kinglets, and northern saw-whet owls.

How many vacation rentals are available around Assateague Island, US?

Our 2021 property listings offer a large selection of 3,803 vacation rentals around Assateague Island. From 34 cabin rentals to 1,139 house rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.