Holiday rentals 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!

Muskrat Town Road Retreat

Your family will be close to everything when you stay at this centrally-located place. Pet friendly! Assawomen Bay access. Don’t miss out on this BEAUTIFUL, ocean accessible two miles from the Freeman Arts Pavilion,1.3 miles from Yellowfin’s bar&grill, 4.5mies from Catch 54 and Harpoon Hannas restaurants,5 miles away from Fenwick island Beaches,5.5 miles from Seacrets famous nightlife ,nine miles from the Ocean City inlet and boardwalk, and hundreds of other places kayak and jet ski friendly

Home Away from Home , Pet friendly retreat

Welcome to Ocean Pines Getaway, Enter home through a beautiful covered porch with swing for two and lovely seating area. This sweet home has 3 bedrooms & 2 full baths. A fully stocked kitchen , with eat in breakfast nook, Also proper dining room plenty of seating for family Cozy living room with working fireplace. All season sunroom plenty of seating, pub table & bar. Doggie door in sunroom large enough for 100 lb dog, leads to fenced in backyard. $100 pet fee and $125 linens & bath towels.

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.

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 :)

Lighthouse Cottage- Pet Friendly & Close to beach

Best deal in the area only 9 miles from Ocean City, MD and Fenwick Island, DE Quiet and away from the noise and traffic at the resorts. Room for your Boat or motorcycle trailers. Close to boat ramps. Close to historic townships. Selbyville DE, Berlin MD, Snow Hill Md and more. Visit Ocean City beaches and boardwalk or maybe you want to explore Bethany beach or Rehoboth beach. Relax with the whole family at this peaceful place to stay. Priced so you don't stray from your budget.

Cozy beach home away from home!

Welcome! Come enjoy a cozy experience at this centrally located home in the desired Ocean Pines Community! This home is near the playground and allows access to the on-site golf course, five pools (including indoor pool!) tennis courts, and marina for a small fee. Fun in the sun awaits 15 minutes away in downtown Ocean City, where you can stroll the boardwalk, lounge on the sand, or hit the amusement park. Plenty of restaurants, grocery stores and shopping within 15 minutes.

Tiny Cottage at Good Earth, near Bethany Beach

Welcome to the "Tiny Thyme Cottage" at Good Earth. The cottage is super cozy, perfect for a couple, with 1 queen bed, a kitchen & bathroom, and a small living area. You'll be staying on our 10-acre property, 4.7 miles from Bethany Beach. Convenient amenities include 2 on-site restaurants, market, theater, and ample parking. Our AIRBNB "Village" includes 2 tiny houses, a lofted apartment, and 2 cottages on the property. Staying at Good Earth is more than just a beach trip!

Hobbs & Rose | A Peaceful Cottage Escape

Built in 1941 from historic “clinker bricks,” this restored cottage is a dreamy place to slow down and reconnect. Surrounded by enchanted gardens and close to the beach, Hobbs & Rose is filled with charm—gorgeous living spaces, a carved marble soaking tub, and thoughtful details throughout. Enjoy a romantic getaway and unwind in our Sanctuary meditation room, where birdsong and forest friends welcome you. You relax—we’ve created every detail to help you feel restored.

SpaciousCondo nearOcean City|Winery|Golf on 5Acres

Come stay in our 2nd Floor Condo on our private 5-Acre Property! Enjoy the Barn-Like look from the outside, but inside, find a modern & spacious condo with a fully-equipped kitchen. Located in Berlin, Maryland, you are minutes to Historic Berlin and only 15 minutes to all the fun that Ocean City, Maryland has to offer! Have your morning coffee on the deck and soak in the scenic views or pitch a tent, light up the fire pit, let the kids run wild! We'll see you soon!

Country Cottage -7 Miles from Fenwick Island Beach

Welcome to PopPop’s Place. This is a cozy, 1,000 sq. ft. 1 bedroom 1 bath cottage that has been on our family’s 20 acre property for more than 60 years. It is located 7 miles west of Fenwick Island, DE and North Ocean City, MD. While we are close to the beaches and attractions, we are also close to multiple golf courses, inland bays for kayaking, crabbing, fishing, entertainment at Freeman Stage-Bayside and many other fun vacation activities.

Drifted Pines - Loft Suite

Keep it simple at this peaceful, private, and centrally-located place. Enjoy the entire upstairs guest house on an old tree farm with many amazing varieties of trees, just 5 miles from the Atlantic Ocean! You will be a quick 10 minute drive from the best of the Delaware and Maryland Beaches. Relax in the shade by day and star gaze with extremely low light pollution at night. We have room for your bikes, kayaks, and trailer.