Holiday houses in Bishopville

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!

Ocean Pines Getaway

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

Central Haven with Great Fenced Yard

You will be close to everything when you stay in this centrally-located home. The rear deck and grill are great for enjoying time outside. There's a fenced rear yard, making this home a perfect choice for man's best friend. We welcome dogs of any breed, size, and weight. We do offer size-specific pet amenities, so please share a photo of your dog when booking, or provide a basic description so we can set out appropriate amenities. For those traveling with cats, please inquire before booking.

Country Private Vacation House

Stay at our lovely home and enjoy a peaceful and quiet country setting. Come back after the beach and cook on the grill and relax in our private home sitting at the end of Derikson Creek. Large wrap around back deck with a view down the creek and into the woods. Plenty of room inside with a large living room, dining room, gourmet kitchen, and 3 bedrooms. Our cozy home is just minutes away from Bayside Resort, Restaurants, Assowoman Wildlife Refuge, and Delaware and Maryland Beaches.

Newly built bright and airy guest suite!!!!

FREE oceanfront parking pass with bookings. 2nd floor private suite with parking, patio/firepit, and self check-in private entry. We are located just minutes from the Ocean City beaches, quaint small town of Berlin, Ocean Downs Casino, Assateague, Windmill Creek Winery, restaurants, and outlets. Enjoy neighborhood amenities such as a waterfront Yacht Club with restaurant and live music (seasonal), golf, farm market, playgrounds, 5 pools/fee, (no pool on property) racquet club.

Beachfront with a View and Amenities Galore

Note: Must be 25 or older to rent our home. Beautifully renovated 2 bedroom beach front condo with views of both the beach and bay. Enjoy watching the waves roll in or a stunning sunrise through floor to ceiling windows without ever getting out of your king size bed. In the evening, open your front door to witness breathtaking sunsets over the bay. Or just relax with a drink on the beachfront balcony and listen to the waves with a breathtaking view of the beach and ocean.

Dewey Beach Condo 2BR+sofa bed. Walk to the beach!

Located near the Town Hall & the Police Department, this charming 2-bedroom ground floor condo is a clean, safe, family-friendly coastal vacation environment! Only 1.5 blocks to the beach, 1 block to beautiful bayside dining, and 5 blocks from downtown Dewey. Fully furnished with 2 queen beds, comfortable sleeper sofa, full bath, washer & dryer, fully equipped kitchen, clean bed sheets & towels, fast WiFi, beach chairs & more. I'm a responsive, experienced SuperHost.

Wagon Wheel Cottage

Remodeled country farm house cottage that was built by our uncle in a quiet rural area surrounded by farm land. Other family members live all around us. It's located in the small town of Powellville, Md. It is 21 miles from Assateague, 20 miles from Ocean City, 12 miles from Berlin, 13 miles from Salisbury and 41 miles from Chincotegue VA. Sorry we do not allow pets as some guest have pet allergies.

Destination Location! Farm Animals, Tours, Beaches

✨Scratch tiny house living off your bucket list!✨ Wake up to the cheerful sounds of barnyard animals that surround this unique tiny house escape! The "Garden Hideaway" is thoughtfully curated to inspire joy and help you reconnect with the simpler things in life. Just a few minutes from the beach, this tiny home comfortably sleeps two (2) guests, with an option to add a third (3) for a small fee.