Holiday rentals in Bishopville

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Top-rated holiday rentals in Bishopville

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Top guest favourite
A vibrant neon sign reading 'Sea Glass Sunrise' is framed by lush green foliage, set against a backdrop of a serene beach at dawn. The soft pastel colors of the sky create a peaceful atmosphere, enhancing the welcoming ambiance of the space.
Apartment in Ocean City
4.99 out of 5 average rating, 121 reviews

Gorgeous New Beachfront! King Bed, Direct Sea View

Stunning beachfront condo with direct view of the ocean! Your vacation home away from home! Everything you need right ON the beach. All linens, supplies and a well-stocked kitchen! New 65" TV w/free 4K Netflix provided! Modern serene decor in the heart of OC! Feel like getting out? Enjoy walking distance to Seacrets, Mackey's, and Fager's Island, Subway, Candy Kitchen or Dumsers' Dairyland! More adventure? Walk to minigolf, pontoon boats and jetski rentals! Only 4 minute drive to the boardwalk!!

Top guest favourite
A cozy living area features a white couch and two accent chairs with a leaf pattern. A glass coffee table sits on a woven area rug. Large sliding doors provide a view of the outdoor patio, framed by greenery and water, enhancing the space's natural light.
Guest suite in Ocean Pines
4.95 out of 5 average rating, 395 reviews

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!

Top guest favourite
The exterior of a single-story house is visible, featuring a spacious front porch with white railings. Large windows allow natural light to enter, while a driveway provides parking for two vehicles. A wooded area surrounds the property, enhancing its peaceful setting.
Home in Ocean Pines
4.98 out of 5 average rating, 137 reviews

Camelot

HIGHEST RATED HOUSE IN OCEAN PINES! CHECK OUT OUR AMAZING GUEST REVIEWS :) Jumpstart your ultimate beach getaway at this impressive 3-bedroom, 2-bathroom retreat house! Complete with amenity-packed living spaces with vaulted ceilings and a serene location, you’ll never hunger for entertainment at this family friendly home. Grill out on the patio, roast marshmallows by the fire pit, tee off at a nearby golf course, or enjoy some retail therapy at Outlets Ocean City! A short drive to the beach!

Top 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
4.94 out of 5 average rating, 146 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.

Guest favourite
The exterior of Rosemary Cottage is displayed, featuring a welcoming entrance with a white path leading to the front door. The cottage showcases a warm wooden shingle façade, surrounded by landscaped grass and small shrubs, set against a backdrop of leafy trees.
Cottage in Ocean View
4.91 out of 5 average rating, 138 reviews

Rosemary Cottage at Good Earth, near Bethany Beach

Welcome to "Rosemary Cottage". It is the perfect size for a small family, with 2 bedrooms (1 queen bed, and 2 single beds) a kitchen, and a 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 another cottage just like this "Basil Cottage". Staying at Good Earth is more than just a beach trip!

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, 87 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
A wooden deck features two light green Adirondack chairs and a small round table, offering a view of the ocean through trees. The horizon showcases a bright blue sky with scattered clouds, enhancing the serene atmosphere.
Home in Milton
4.99 out of 5 average rating, 105 reviews

BeachHaven: STEPS TO SAND, Pet-Friendly, +Linens

Peaceful, secluded, tranquil, yet close to attractions. Our home is located at the more private (i.e. no crowds) southern end of Broadkill. The boardwalk in front of our home leads to the beach path access across the street. You will enjoy views from both the front and back decks: including the beach & Prime Hook Wildlife Refuge. If this property is booked or you need multiple homes for a group, we host several nearby beach homes. Click on my host profile to see them.

Top guest favourite
A charming cottage facade is framed by white columns and features a gabled roof. Two black rocking chairs, adorned with pillows, sit on a brick porch surrounded by colorful potted flowers. Lush greenery enhances the inviting atmosphere.
Cottage in Frankford
5 out of 5 average rating, 213 reviews

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.

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
4.95 out of 5 average rating, 82 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!

Top guest favourite
The exterior of a two-story house is displayed, featuring a wraparound porch and a driveway surrounded by trees. A garage is visible on the left side, and the front yard is landscaped with grass and stone pathways.
Guest suite in Frankford
4.95 out of 5 average rating, 151 reviews

Quiet setting on private pond among the wildlife

Enjoy a quiet, private setting just 3 miles from the Bethany Beach boardwalk. Nestled across from the Assawoman Wildlife Refuge, you can relax in a spacious home away from home. Plenty of room for the kids to play outside while you relax on the dock overlooking the pond. Guests have access to the second floor of the home which includes a full size kitchen, 3 bedrooms and living room that all have Smart TVs. Plenty of parking for you and guests.

Top guest favourite
A wooden dock extends over calm water, surrounded by tall trees. A pair of Adirondack chairs provide a peaceful spot to enjoy morning sunlight filtering through leaves, creating a serene atmosphere perfect for relaxation.
Home in Newark
5 out of 5 average rating, 104 reviews

Secluded Waterfront 15mi to Beach•Kayaks•Fast WiFi

Casa Blue Heron is a 2,254 ft² (209 m²) custom home offering stunning water views, a firepit, and serene seclusion at our 3-bedroom waterfront sanctuary by Chincoteague Bay and near Assateague, Berlin, Ocean City, Snow Hill and much more. ★ "A private and tranquil setting where it is impossible not to relax and appreciate nature... Wish I had booked an extra day!" Add us to your wish list by clicking the❤️in the upper-right corner.

Top guest favourite
A living area is characterized by a spacious sectional sofa, positioned under a vaulted ceiling with exposed beams. Natural light enters through a skylight and a window, illuminating a mounted television and a decorative side table, enhancing the room's clean and inviting design.
Home in Ocean Pines
5 out of 5 average rating, 18 reviews

Cozy Coastal Home in Ocean Pines

Our home is 2 bedrooms, 2 full bathrooms, detached house, with a rear deck and patio with dining table located in Ocean Pines. It's updated & modern, clean, and ready for your next beach vacation! The house has a fenced in yard and is in a very quiet neighborhood and will make a great family vacation home. We cater to families, couples and small groups.

Popular amenities for Bishopville holiday rentals

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