Where to stay around Assateague Island?

Our 2019 property listings offer a large selection of 3,337 vacation rentals near Assateague Island. From 2,261 Condos/Apartments to 442 Houses, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends. The best places to stay near Assateague Island are on HomeAway.

What are the most popular destinations to visit in Assateague Island?

There are many lovely places to stay for a holiday trip or just for a weekend in Assateague Island. From HomeAway travelers, the most popular destinations to visit are:

  • Ocean City: 4,792 vacation rentals
  • Bethany Beach: 5,216 vacation rentals
  • Virginia: 8,192 vacation rentals
  • Ocean View: 1,852 vacation rentals
  • Fenwick Island: 4,836 vacation rentals

And HomeAway offers you the chance to discover many other popular destinations in Assateague Island! Please use our search bar to access the selection of vacation rentals available in other popular destinations.

What are the main cities to discover in Assateague Island?

Whether you're traveling with family or friends, here are the cities with the largest selection of vacation rentals for a holiday trip or just for a weekend in Assateague Island:

  • Ocean City: 4,792 rentals
  • Bethany Beach: 5,216 rentals
  • Ocean View: 1,852 rentals
  • Fenwick Island: 4,836 rentals
  • Chincoteague Island: 129 rentals

For other cities, please use our search bar to access the selection of vacation rentals available.

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?

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.

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.

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.

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.

Explore destinations around Assateague Island

Ocean City
4,792 vacation rentals
Bethany Beach
5,216 vacation rentals
Ocean View
1,852 vacation rentals
Fenwick Island
4,836 vacation rentals
Chincoteague Island
129 vacation rentals
Ocean Pines
3,884 vacation rentals
Chincoteague
125 vacation rentals
Selbyville
2,659 vacation rentals
South Bethany
3,011 vacation rentals
Berlin
3,685 vacation rentals
Millsboro
2,272 vacation rentals
West Ocean City
3,519 vacation rentals
Millville
1,362 vacation rentals
Frankford
4,334 vacation rentals
Assateague Island
122 vacation rentals
Temperanceville
64 vacation rentals
Long Neck
355 vacation rentals
Parksley
19 vacation rentals
Sussex Shores
1,403 vacation rentals
Snow Hill
3,093 vacation rentals