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Holiday rentals in Bishopville

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Top-rated holiday rentals in Bishopville

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A single-story home is set within a spacious yard, bordered by greenery. Light-colored siding and red shutters frame the windows, while a paved driveway leads to a set of steps ascending to the entryway. A small shed is visible in the yard.
Home in Bishopville
5 out of 5 average rating, 18 reviews

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

Top guest favourite
A welcoming space is featured, showcasing a luxurious jacuzzi with a wooden tray holding candles and decor. Nearby, a cozy living area with a modern couch is highlighted against an artistic forest mural. An adorable Highland cow stands nearby, adding a touch of rustic charm.
Ranch in Selbyville
4.98 out of 5 average rating, 300 reviews

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.

Top guest favourite
A serene waterfront scene is captured at sunset, with vibrant colors reflected in the calm water. A charming building with large windows is illuminated, surrounded by lush trees, and boats are docked along the waterfront, creating a peaceful atmosphere.
Apartment in Ocean Pines
4.97 out of 5 average rating, 218 reviews

Water view at Ocean Pines Yacht Club Condo

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

Guest favourite
A living room features light blue seating arranged around a coffee table, complemented by a decorative cabinet and a large television. Natural light filters through the window, enhancing the tranquility of the space, which is accented by a ceiling fan and wall art above the entrance.
Home in Selbyville
4.93 out of 5 average rating, 161 reviews

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.

Top guest favourite
A large window displays a view of the serene farm landscape. A single horse grazes in the grassy field, with a tree and a rustic barn visible in the distance. Soft light from the setting sun casts a warm glow over the scene.
Loft in Pittsville
4.94 out of 5 average rating, 36 reviews

Peaceful country setting near the Beach

Welcome guest, our small farm is quaint and peaceful with farm life all around us. Birds chirping and horses grazing ( please no petting) Our farm is 15 minutes from Salisbury, Md where we have the Salisbury Zoo, and great restaurants. We are also 30 minutes from Ocean City, Md where we have the famous Thrashers Fries and boardwalk. Assateague National Seashore is also 30 minutes away where you can bike ride, kayack, or just walk the trails. The wild ponies of Assateague are a must see.

Top guest favourite
A private patio is visible, presenting two comfortable chairs positioned on a white wooden deck. The space is framed by a rustic wooden wall and lush greenery, while a brick pathway leads to the entrance. A flower pot adds a touch of color to the setting.
Place to stay in Frankford
4.97 out of 5 average rating, 118 reviews

The Beach Cabin, NO WI-FI

This private room is small, basic and rustic. Nestled in the back of the property, it offers a comfy queen bed, AC, small heater, a mini fridge, Keureg style coffee maker, in room toilet, outside shower and sink with hot water, private patio, clean linens and towels. Backyard has sitting areas and chimnea with firewood provided. Quiet neighborhood. Bethany Beach -10 min drive, Rehoboth-25 min. Beach gear available. TY. For current backyard blooms check on insta: glamping_with_the_flowers

Guest favourite
A functional kitchen space features warm wood cabinetry and modern appliances, including a stove and microwave. A small dining area with four wooden chairs surrounds a table, providing an inviting spot for meals. Light enters through a nearby window, enhancing the bright atmosphere.
Home in Berlin
4.95 out of 5 average rating, 98 reviews

Martha’s Getaway

Newly (3) BR (2)Bath, Master suite has it own walk-in shower. Fully furnished with all new appliances. Central Air, WiFi, Flat Screen TV. Outdoor grill, Front and Backyard, Driveway For Parking! Five minutes away from Ocean City Maryland and Assateague Island! Various Fine Restaurants, Tanger Outlets, Frontier Town, Beach Bounce for your children, Ocean Downs Casino, Until 11pm Super Walmart all for your convenience at Martha’s Getaway! The happiest little town in Berlin Maryland! No pets!

Guest favourite
A bright blue door, adorned with a floral wreath, is framed by a small, welcoming porch area. A 'Welcome' doormat sits at the entrance, while two white chairs are positioned on either side of the porch railing, inviting guests to relax.
Flat in Millsboro
4.94 out of 5 average rating, 17 reviews

Coastal Castaway

Cozy and completely remodeled, this charming two-bedroom, one-bath apartment is the perfect beach getaway! Comfortably sleeping up to six with a pull-out couch in the living room, this home offers plenty of parking for your watercraft. Enjoy the screened porch with a table & chairs to relax. After a day at the beach just 15 miles away refresh in the convenient outdoor shower. With a public boat ramp 2.8 miles away and the Indian River just steps away! Pack your bags and get ready to unwind!

Top guest favourite
The entrance to the Clayton House is framed by lush ivy. The white facade of the home is complemented by a wide porch with two matching wooden doors, tall white columns, and a light fixture. A stone walkway leads to the porch, bordered by well-maintained greenery.
Home in Dagsboro
5 out of 5 average rating, 21 reviews

The Garden at Clayton House

This newly renovated home in the heart of Dagsboro is a peaceful garden getaway. Visitors are perfectly situated to enjoy the world-class Delaware Botanic Gardens and are minutes to Millville, Ocean View and the DE & MD beaches. From Clayton house you can walk to charming antique & gift shops, a diner style restaurant, a cafe with coffee and ice cream, a toy store, a quilt shop, a barber shop and beauty parlor, a movie theater and a beautiful park. Come experience the charm of Dagsboro.

Top guest favourite
A well-maintained house features a light-colored exterior surrounded by landscaped flower beds. A gravel driveway leads to the entrance, which is adorned with potted plants. Lush greenery and a distant building are visible in the background beneath a partly cloudy sky.
Home in Selbyville
5 out of 5 average rating, 89 reviews

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.

Top guest favourite
The interior of the bus features a cozy layout with wood paneling and large windows providing natural light. A comfortable seating area, equipped with pillows, is situated next to a compact kitchen with a stove and cabinets. A small dining table with two placemats is visible.
Bus in Frankford
4.96 out of 5 average rating, 157 reviews

Delightful Skoolie Near Bethany Beach

Try tiny living! Come to the Delaware beach for a unique glamping experience. The Coastal Cruiser is a 1985 Thomas School Bus turned tiny home. Spend your days exploring the Delaware Coast and come home to a rustic Skoolie with a full kitchen & outdoor area. You have access to fire pit, grill, and outdoor seating area. We’ve renovated- there is a bunk bed, and a full bathroom with toilet, shower, and sink. The bathroom is in a separate building about 20 ft from the bus.

Top guest favourite
A barn-style exterior of the condo is showcased, featuring a metal roof and three large garage doors at ground level. The second floor includes a deck with an entrance door. Expansive green space surrounds the property, with trees visible in the background under a clear blue sky.
Home in Berlin
4.96 out of 5 average rating, 100 reviews

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!

Popular amenities for Bishopville holiday rentals

  1. Airbnb
  2. United States
  3. Maryland
  4. Worcester County
  5. Bishopville