Holiday rentals with beach access in Assateague Island

Adorable Beach Cottage Just Steps From Town & Bay

New to AirBNB! Welcome to Wiggle Bay, a darling 1955 2 BR cottage nestled in the heart of "one of the most beautiful, charming small towns in Virginia." -Enjoy a bay breeze on the screened front porch--heaven! --Stroll to local bookshop, coffee house, theatre, or Chincoteague Waterfront Park to feed the ducks--all just steps from your front door! -Situated on a quiet residential street -Just 4 blocks to Maddox Blvd (where all the action is) -2.3 mi to Assateague Seashore/Chincoteague Refuge

Stunning private waterfront suite

Welcome to your cozy getaway with stunning water views from every room! This sweet 2-bedroom, 1-bath suite boasts a private entrance, a living room, and a cute kitchenette. Nestled in a peaceful, family-friendly neighborhood, you'll have year-round access to swimming pools, a golf course, tennis courts, a Yacht club, and lovely parks nearby. Only a quick 10-minute drive lands you on the sandy beaches and lively Boardwalk of Ocean City. Park in the driveway and step into your own private escape!

Ranch Stay- Farm Animals, Jacuzzi, Arcade, Beaches

Welcome to the Swedish Cowboy, your ultimate escape! This unique BARNDOMINIUM home is designed to offer a memorable retreat for up to four (4) guests, with the flexibility to accommodate two (2) additional guests for a small fee. Enjoy the charming backyard where you can meet a variety of fuzzy and feathered friends or head inside and play on the arcade or relax in the jacuzzi. Perfectly situated near popular beaches and bustling boardwalks, you'll have plenty of options for fun and relaxation.

Waterfront-CI Bay sunsets-Amazing views

Wide expansive waterfront view of Chincoteague bay-awesome sunsets! 5 waterview rooms. The narrow bit of land across 3446 Main St. belongs to our property w/chairs + a firepit + water access to launch kayaks (2) provided! An open plan-coastal rustic design. Front sitting room w/sofa + high-top table. A large upscale kitchen, two sofas in living room, 2 bdrms, & sleeping loft + a tiny office with a twin murphy bed. Large deck-table, sofa + grill. Family home, not ideal for more than 3 adults.

Ocean Pines Retreat

Steps to 2 pools, 2 marinas, tiki bar and OP Yacht Club. Live music Thursday-Sunday evenings from 6-10pm, (in season). Beach day? Ocean City 15 min drive or walk to the marina and hop on a boat with friends and head across the bay into OC. Assateague Island is a 20 min drive. Crabbing? Fishing? Walk to one of the many Ocean Pines canals or ponds. Golfing? The links are just across the Parkway. Wedding party? Be footsteps away from make lasting memories. Free beach parking on 49th included

"3 Sisters" Ivy's Cottage-Lovely downtown cottage

Just a few miles from the Chincoteague National Wildlife Refuge & Assateague Beach. Ivy's Cottage offers a great in-town location that's close to shops, restaurants, waterfront park, & public fishing pier. This beautifully renovated, this Chincoteague Island Cottage Features: Lovely eat in kitchen, fully equipped w/ all amenities. Cozy living room w/ full sleeper sofa & recliner. Queen bedroom w/ adjacent full bathroom. Large front porch perfect for outdoor dining & park style charcoal grill!

On a Whim, a family retreat!

Relax with the family at our home, nestled on a quiet private street yet just a short walk from restaurants, beach access, and family-friendly activities. Enjoy access to all that Chincoteague has to offer while retreating to a cozy & comfortable Cape Cod-style duplex. We are a short drive away from exploring Chincoteague National Wildlife Refuge, famous for its wild ponies and hiking trails. Whether you’re here to relax or adventure, this local gem offers something for every nature lover.

Edgewater Escape - Luxury Bayfront Loft with Porch

You've never seen waterfront like this. Welcome to Edgewater Escape, a luxury bayfront loft apartment that hangs entirely over the bay on 7th street in downtown Ocean City. Sit on the bay front porch or hang out inside and watch boats, dolphin, birds, and sometimes even seals swim by within feet of the porch. The loft has a roomy king sized bed and the downstairs couch pulls out into a comfy queen bed. Recently renovated, it comes fully equipped for your big trip or quiet staycation :)

Stunning waterfront panoramic view getaway house

Welcome to this thoughtfully remodeled waterfront property on the beautiful eastern shore of Virginia. Immerse yourself in jaw-dropping panoramic canal views of the Chincoteague Bay. Secluded escape for the nature enthusiast, balanced with country club amenities. Pools, boating and a golf course are within walking distance. Outdoor adventures and pristine beaches are just a short drive away! This property was designed to gather, recharge, explore, love, work remotely and inspire.

Rumbley Cottage on the Tangier Sound-Private Beach

LAST MINUTE OPENING-09-27 to 10-03-25 !!!! Rumbley Cottage, a custom-built home, provides a quiet stay in nature. Views from all windows. Look out at the mouth of the Manokin River at Tangier Sound on one side; wetlands on the other side. NO CLEANING OR PET FEE. Rumbley Cottage is enjoyed year- round with a great fireplace. WE PROVIDE THE FIREWOOD AND STARTERS. Many amenities including Molton Brown toiletries, kayaks, SPBs, bikes, beach equipment; well-stocked kitchen.

"Jolly"- Houseboat Getaway

#BoatLife! Jolly is a 42ft Holiday Mansion. Baywater Landing offers a laid back, coastal style. It buzzes with watermen & boaters by day & is a peaceful stargazing hotspot by night. She features a master suite & 3 outside deck areas to enjoy! Just 35 minutes from Ocean City, Assateague Island, and Chincoteague Island, this is the epicenter of everything coastal! A firepit in the sand just outside your door round out everything you'll need for a stress-free vacation.

CANAL FRONT Wi-Fi, Roku, Netflix, boatslip, pool

BEAUTIFUL WATER VIEW ON 28 STREET.1 bedroom apartment with full kitchen and bath. Bedroom has 2 full size beds, boat slip and boat ramp. 1 onsite parking spot included, plenty of parking available in front of building. Public transportation close by. Walk to beach,boardwalk, restaurants, miniature golf, go cart tracks, Jolly Rogers Amusement and Water park. Free WiFi, Netflix, Hulu, and Roku to connect to your streaming services. Coded entrance. Beach gear.