Townhouse holiday rentals in Assateague Island

3 min OC Boardwalk, Jolly Rogers Park, Sleeps 8

Unwind in our cozy 3bd/2 bath, canal-front, coastal retreat, 1/3 mile from the 27 St OC boardwalk. Fully-furnished, our townhome accommodates 6 adults and 2 children, includes linens & towels, and comes with a fully stocked kitchen. Relax with WiFi and 3 x 42-in. flat screen TVs. Enjoy morning coffee and sunset drinks on our furnished deck by the canal. Guests have access to 8 beach chairs, a cooler, and 1 umbrella. Minutes from local favorites like Hooked, Liquid Assets, and Bayside Skillet.

Family · Location · Barbecue

Sunset View - Views-Sunsets-Waterfront w/40' Pier

Located just a few miles from the Chincoteague National Wildlife Refuge & Assateague Beach, Sunset View checks off all the boxes! Enjoy the new 40' dock, great for fishing, crabbing, boat docking!! Enjoy sunsets over Chincoteague Bay from the decks! Crab and enjoy nature from a private pier on the creek. Queen Bedroom & a shared full bath on the 1st floor. King Bedroom w/ Private Bath & Waterview Deck on 2nd Floor. Queen Bedroom w/ Private Bath on the Second Floor & 2 Twin Folding Beds.

Family · Location · Parking

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.

Value · Family · Parking

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 :)

Value · Location · Hospitality

OceanPinesFamilyBeachRetreat~JettdTub~KingBed~Golf

Immediate removal of stress at the front door. Being nestled in a marina’s serene waterfront & nature park is good for the soul. Relax in a jetted tub after a sun filled day & an al fresco meal on a back porch with charming outdoor dining. An open concept main level features large windows & comfortable seating through the entire property. 2 full bathrooms upstairs & a king sized bed provide maximum comfort & outdoor living on 2 balconies. Additional fees for pools, pets may apply.

Location · Family · Decor

DownByTheBay 214-Sleeps 15/Downtown/Boardwalk/Pool

Come and enjoy this oasis, accommodates 15, this 3 BR 3.5 BA home is in the heart of Ocean City MD, minutes from the beach & located steps away from Ocean City most popular attraction, The BOARDWALK. There is everything you will need for a large group to retreat (fully equipped kitchen), 2 large balconies, 2 car parking plus community & street parking, outdoor pool *This property DOES NOT provide linens/towels* ***Please FIND us @ Down by the Bay OCMD For current Promotion**

Value · Location · Beach

Awesome 28th Street Beach Block Location!

Oceanside Townhouse on 28th Street less than 100 steps from beach with upgraded main level bathroom, kitchen, flooring, appliances, granite counters. Private driveway - ocean views from 2 balconies! Fantastic location, 1 block from boardwalk, restaurants, Jolly Roger, Mini Golf & water park. The house feels like home with full kitchen & laundry room. Space for a large group to be comfortable. Linens (sheets & bath towels) included. Responsible person must be at least 21.

Value · Family · Getting around

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!

Family · Location · Getting around

‘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!

Location · Value · Pool

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.

Family · Value · Walkability

Gorgeous home on Chincoteague-Misty Mare Townhouse

Relax in the quaint fishing village with the horses that made Chincoteague Island famous, featuring a relaxing country living space with just the right touch of modern amenities. This “home away from home” also features two spacious bedrooms, two bathrooms, and an eat-in kitchen with brand-new appliances. 10 minute drive from Assateague Beach, and minutes from restaurants, boutiques, and many outdoor activities.

Value · Family · Parks

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.

Family · Location · Cleanliness