Townhouse holiday rentals in Assateague Island

3 mins to Beach/28 St boardwalk/Jolly Roger Park

Come vacation at Serenity by The Sea, a 1120 sq. ft. fully furnished 3bd/2 bath townhome 1/3 mile from the 27th Street OC boardwalk. The home accommodates 6 adults + 2 children and comes with a fully stocked kitchen. Relax in front of one of three 42-inch flat screen TVs with WiFi. Enjoy drinks on our large, furnished wooden deck overlooking the canal. Guests are invited to use our beach chairs, cooler, and umbrella. Minutes from exceptional dining at Hooked, Liquid Assets, or Bayside Skillet.

IslandCoveParadise:LuxNewlyBuilt-Brdwk pool/2CarGg

We welcome you, your family and friends to stay at our luxury, Newly Built, beautifully furnished, & decorated 3 BR 3.5 BA w/2 parking garage spaces plus free street parking, and an outdoor pool on 25th street. Relax and enjoy the AMAZING VIEW on the water front from our triple balconies, just 2 blocks (3-4 minutes walk) from the boardwalk & the beach. Steps from Jolly Rogers Amusement Park and many miniature golf courses. Within walking distance are restaurants/, shopping, & nightlife.

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 :)

86th Oceanfront / 4 BRs / sleeps 10

Welcome to your beachfront oasis in Ocean City! Nestled on the sandy shores, this charming 4-bedroom townhome boasts the perfect blend of classic beach vibes and modern comforts. Step inside to discover inviting old-school pine walls complemented by contemporary touches. With multiple balconies offering stunning ocean views, you'll wake up to the soothing sound of waves. Come lounge in the sun-soaked living spaces this rental provides for an unforgettable coastal retreat.

Fenwick Island Sunset Retreat

Charming Coastal Retreat with Breathtaking Open Bay Views Welcome to East of the Sunset. Located on the state boarder where Fenwick Island DE meets Ocean City MD. With 2 spacious bedrooms (king, queen, ), there's plenty of room for everyone to relax. The property offers fantastic on-site amenities, including a pool, tennis, and pickleball courts, ensuring endless fun during your stay. Close to the Beach, Restaurants, waterpark, mini-golf and everything at the beach.

McKinley Duplex

Enjoy the Ocean and Bay Views from the roof top deck of this Pet Friendly duplex located in the ocean block in the heart of Dewey Beach! Just steps to the beach with a large enclosed porch, open living area, 6 bedrooms and 3.5 baths (2 King, 1 Queens, 6 Twins and a sofa bed), ample parking and much more. Walk to all the restaurants and nightlife - take the Jolly Trolley into Rehoboth to enjoy the beach, boardwalk and some of the finest dining in the area!

Luxury Townhome close to OC beach & boardwalk!

Welcome to your ultimate getaway in our brand new luxury townhome! This stylish, three-story home offers over 2,500 sq. ft. of space and is perfect for families or groups, comfortably sleeping up to 11 guests. Just 3 miles from the Ocean City Boardwalk, you’ll have easy access to the beach, shops, restaurants, and endless fun. Enjoy resort-style living at Sea Oaks, ideally located between Ocean City and Assateague Island. Your perfect vacation spot awaits!

‘Dockside Retreat’ -pool, minutes to OC/beaches

Escape to Dockside Retreat in Bayville Shores, a private community on the scenic Little Assawoman Bay. Start your mornings with beautiful views, unwind with community amenities, or head out for adventure. Splash at Thunder Lagoon, race at Viking Go-Karts, or shop and dine by the coast. Beaches are just minutes away—Fenwick Island (2.5 mi), State Line (2.7 mi), Bethany (4.5 mi), and Ocean City (6.1 mi). The perfect blend of relaxation and fun awaits!

Bayfront Townhouse: Fishing, Sunsets & Family Fun!

Escape to this stunning, updated bayfront townhouse in midtown Ocean City! Featuring 3 bedrooms with 3 ensuite bathrooms, enjoy breathtaking sunsets from your private deck. This entertainer's dream offers a spacious open layout with a gourmet kitchen and waterfall countertops. Benefit from two assigned parking spots, fish directly off the back deck pier, a local favorite fishing spots, you'll love the waterfront access and relaxing atmosphere.

Bayfront 3-Bed Townhome W/Linens & Beach Gear.

Welcome to our Dewey Beach House! While staying here, you can expect a sun-filled, clean, relaxing space with an unbeatable location and an incredible view of the Rehoboth Bay. You are only: - 5 minute walk to the beach. - 5 minute walk to the Starboard, Bottle & Cork, and many other Restaurants and shops in town. - 2.5 miles to downtown Rehoboth Beach. Come experience what makes Dewey Beach & this stay so special!

Lover's Cove

3 Bedroom Townhouse-Minutes to Rehoboth Avenue and the beach. Rehoboth Avenue is .4 miles away. The ocean is .8. We are on the Ocean side of route 1. Great patio for dining, equipped with Weber propane grill, outdoor shower, beach chairs, tiki bar and patio set with umbrella. Wifi, cable and a dedicated work space. Lover’s Cove offers all modern amenities for your enjoyment and is decorated in modern decor.

Beach, Boardwalk n Fun- just steps to the beach

Newly Renovated in 2025 4 Bedroom, 3 Full Bath with an AMAZING Location!!! Oceanside with beach access in less than 100 steps. Boardwalk entrance a block away and dedicated single car parking below unit. Central AC/Heat! Excellent High Speed WiFi!! Washer and Dryer in unit. Great for families and groups with 4 bedrooms and 3 bathrooms.. Pet fee $100 Extra fee for guests above 10 guests