Bishopville holiday rentals

We found 8,485 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Bishopville that are perfect for your trip. Whether you're travelling with a group or just with your pet, holiday homes have the best amenities for hanging out with the people that matter most, which might include a garden and hot tub. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Bishopville

Showing deals for:20 Nov - 27 Nov

Exterior
Pool
Fitness facility
Private kitchen
Exceptional
(47 reviews)

Bayside Resort Golf Club Townhome-Walk to pool, playground, tennis. Sleeps 11

Selbyville

8% off
AU$3,907
for 7 nights, 1 home
AU$558 per night
includes taxes & fees
Bayside Resort Golf Club Townhome-Walk to pool, playground, tennis. Sleeps 11
Living area
Private kitchen
Dining
Room
Exceptional
(29 reviews)

Newley Renovated Beach Home, Min. to Ocean City,1st FL. Master Suite, walk in

Berlin

8% off
AU$3,596
for 7 nights, 1 home
AU$514 per night
includes taxes & fees
Newley Renovated Beach Home, Min. to Ocean City,1st FL. Master Suite, walk in
breakfast bar
Outdoor dining
Spacious bright and airy living room off the den and kitchen
Room
Exceptional
(63 reviews)

Gorgeous Bethany retreat! Dog friendly, 4 BR/3BA, near trails, <2 miles to beach

Bethany Beach

8% off
AU$3,776
for 7 nights, 1 home
AU$539 per night
includes taxes & fees
Gorgeous Bethany retreat! Dog friendly, 4 BR/3BA, near trails, <2 miles to beach
Kitchen
Sunroom
Kitchen / Living Room
Sunroom
Exceptional
(124 reviews)

Pet Friendly Near Berlin, Assateague Island Beaches and Ocean City

Berlin

7% off
AU$1,893
for 7 nights, 1 home
AU$270 per night
includes taxes & fees
Pet Friendly Near Berlin, Assateague Island Beaches and Ocean City
Private kitchen
Great sunset views of the bay!
Property grounds
Nice fireplace with 50” flatscreen tv above
Exceptional
(142 reviews)

BEAUTIFUL & CLEAN! Waterfront condo with epic sunsets and a POOL!

Ocean City

7% off
AU$2,031
for 7 nights, 1 apartment
AU$290 per night
includes taxes & fees
BEAUTIFUL & CLEAN! Waterfront condo with epic sunsets and a POOL!
Living area
Property grounds
Exterior
Private kitchen
Exceptional
(105 reviews)

Huge Direct Oceanfront Townhouse with Beautiful Sunrises

Ocean City

7% off
AU$3,305
for 7 nights, 1 home
AU$472 per night
includes taxes & fees
Huge Direct Oceanfront Townhouse with Beautiful Sunrises
Interior
Open from Memorial Day weekend through Labor Day
Living area
Private kitchen
Exceptional
(128 reviews)

GorgeousTownhouse,Bay Views, pool, short walk to Ocean, Free WiFi, linens inc.

Ocean City

8% off
AU$4,233
for 7 nights, 1 home
AU$605 per night
includes taxes & fees
GorgeousTownhouse,Bay Views, pool, short walk to Ocean, Free WiFi, linens inc.
Dining
Sunridge pool. Two pools and splash zone. (Must buy a resort pass)
Splash zone at sun ridge pool.
Screened in porch
Exceptional
(31 reviews)

Bayside Resort-One floor 2400sq ft condo,Steps to Sunridge,semiprivate elevator

Selbyville

8% off
AU$4,287
for 7 nights, 1 apartment
AU$612 per night
includes taxes & fees
Bayside Resort-One floor 2400sq ft condo,Steps to Sunridge,semiprivate elevator
Screened-in deck
Back deck off of bedroom and screened-in deck off of living room.
Kitchen
View of playground from back deck
Exceptional
(202 reviews)

Gorgeous Renovated Townhouse-MUST BE OVER 25 TO RENT

Ocean City

8% off
AU$2,223
for 7 nights, 1 home
AU$318 per night
includes taxes & fees
Gorgeous Renovated Townhouse-MUST BE OVER 25 TO RENT
MASTER BEDROOM
LIVING ROOM
ADAGIO UNIT 207
LIVING ROOM
Exceptional
(94 reviews)

ADAGIO#207 BEAUTIFUL 3 BED/3 BATH OCEAN BLOCK CONDO W/INDOOR POOL STEPS TO BEACH

Ocean City

8% off
AU$3,276
for 7 nights, 1 apartment
AU$468 per night
includes taxes & fees
ADAGIO#207 BEAUTIFUL 3 BED/3 BATH OCEAN BLOCK CONDO W/INDOOR POOL STEPS TO BEACH
Diamond Head - less than a half block to the beach and close to many OC attractions
Kitchen with all major appliances and 2-seat breakfast bar
Beautiful ocean views
Welcome to Diamond Head 305 - 1 bedroom, 1.5 bathroom oceanview with building pool
Exceptional
(12 reviews)

Private Pool Steps From the Beach

Ocean City

7% off
AU$1,906
for 7 nights, 1 apartment
AU$272 per night
includes taxes & fees
Private Pool Steps From the Beach
Comfortable and sunny living room
If you're not familiar with Sea Colony, check out seacolony.com
One of Sea Colony's 12 pools, all heated, in/outdoor.
Great view of the Swan Pond
Exceptional
(164 reviews)

Sea Colony, Walk to Beach & Tennis--Beautiful, Sparkling Clean Getaway!

Bethany Beach

8% off
AU$2,163
for 7 nights, 1 apartment
AU$309 per night
includes taxes & fees
Sea Colony, Walk to Beach & Tennis--Beautiful, Sparkling Clean Getaway!
Relax, Have dinner, Play games, see the ocean!
view from balcony to living area
Ocean Front view of the Pyramid the most unique building on the beach
Interior
Exceptional
(101 reviews)

Escape to The Ocean! , Ocean Front, Beautiful View, Pool!

Ocean City

7% off
AU$2,400
for 7 nights, 1 apartment
AU$343 per night
includes taxes & fees
Escape to The Ocean! , Ocean Front, Beautiful View, Pool!
Pool
Living Room and Dining Room
Northside Park within 2-3 blocks
View from bedroom through the kitchen, to the living room and balcony
Exceptional
(43 reviews)

Moos Casa Sea Casa, beach side, private balcony, outdoor pool

Ocean City

11% off
AU$2,068
for 7 nights, 1 apartment
AU$295 per night
includes taxes & fees
Moos Casa Sea Casa, beach side, private balcony, outdoor pool
Living area
Pool
Exterior
Interior
Exceptional
(59 reviews)

Bear Trap Dunes: Spacious and Sparkling 3 Bedroom with All the Amenities!

Ocean View

8% off
AU$2,265
for 7 nights, 1 home
AU$324 per night
includes taxes & fees
Bear Trap Dunes: Spacious and Sparkling 3 Bedroom with All the Amenities!
Room
Pool
Beach
Wonderful
(67 reviews)

OCEANFRONT! 2025 Prime Weeks Available! Great Views! Covered Pool in Summer!

Ocean City

12% off
AU$3,336
for 7 nights, 1 apartment
AU$477 per night
includes taxes & fees
OCEANFRONT! 2025 Prime Weeks Available! Great Views! Covered Pool in Summer!
Room
Exterior
Interior
Bathroom
Exceptional
(89 reviews)

Great Location for your vacation. Very Pet Friendly!. Close to Boardwalk/Beach.

Ocean City

8% off
AU$3,555
for 7 nights, 1 apartment
AU$508 per night
includes taxes & fees
Great Location for your vacation. Very Pet Friendly!. Close to Boardwalk/Beach.
Living area
Exterior
Room
Private kitchen
Exceptional
(9 reviews)

Broad Marsh Beach Home | Pool + Balcony Views

Ocean City

5% off
AU$3,746
for 7 nights, 1 apartment
AU$535 per night
includes taxes & fees
Broad Marsh Beach Home | Pool + Balcony Views
Property grounds
Relax on a chaise in the fresh ocean air
Exterior
Fully stocked kitchen with breakfast bar seating
Exceptional
(159 reviews)

Ocean Front Serene Coastal Views

Ocean City

7% off
AU$4,001
for 7 nights, 1 apartment
AU$572 per night
includes taxes & fees
Ocean Front Serene Coastal Views
Private kitchen
Living area
Dining
Dining
Exceptional
(53 reviews)

No need to look any further for a one bedroom in OC. Long term rates available.

Ocean City

7% off
AU$2,133
for 7 nights, 1 apartment
AU$305 per night
includes taxes & fees
No need to look any further for a one bedroom in OC. Long term rates available.
Heated Indoor Pool
Balcony View
Building Hallway
Living room ocean view window
Excellent
(99 reviews)

Spacious Ocean View Condo

Ocean City

6% off
AU$1,809
for 7 nights, 1 apartment
AU$258 per night
includes taxes & fees
Spacious Ocean View Condo
Interior
Interior
Property grounds
Private kitchen
Exceptional
(63 reviews)

Beachfront living near Seacrets! Don't let this memorable getaway pass you by.

Ocean City

8% off
AU$2,683
for 7 nights, 1 apartment
AU$383 per night
includes taxes & fees
Beachfront living near Seacrets! Don't let this memorable getaway pass you by.
Indoor Pool (Open Summer months Only)
Winter is a Great Time to Enjoy the Beach!
Private kitchen
Lit Entry Hall to Condo - Front Door on Right.
Exceptional
(29 reviews)

Direct Ocean Front...In The Middle of it All!!!

Ocean City

6% off
AU$5,741
for 7 nights, 1 apartment
AU$820 per night
includes taxes & fees
Direct Ocean Front...In The Middle of it All!!!
Private kitchen
Property grounds
Exterior
Living area
Exceptional
(109 reviews)

Direct Oceanfront 3 bedroom condo perfect for family and friends with pools

Ocean City

7% off
AU$2,232
for 7 nights, 1 apartment
AU$319 per night
includes taxes & fees
Direct Oceanfront 3 bedroom condo perfect for family and friends with pools

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Delight in the picturesque landscape of Bishopville

The island views and other outdoor surroundings create an inviting atmosphere in Bishopville. This city is well-known for its golfing and boating. Maryland Beach and Ocean City Beach are just a couple of the must-see attractions in the area. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Sightseeing in and around Bishopville

Do you want to discover attractions to see during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Bishopville a fun spot to go on holiday. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Bayside Resort Golf Club (4.7 mi / 7.5 km)
  • Carousel Ice Skating Rink (7.6 mi / 12.2 km)
  • Bear Trap Dunes Golf Club (7.9 mi / 12.7 km)
  • Jolly Roger Amusement Park (8.5 mi / 13.7 km)
  • Trimper's Rides (9.8 mi / 15.8 km)
  • Jolly Roger at the Pier (9.8 mi / 15.8 km)

Exploring the natural landscape of Bishopville

Whether you're looking for fun outdoor activities or just want to take in the scenery, Bishopville is a great place to get out in nature. Here are some of the area’s most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Maryland Beach (7.8 mi / 12.5 km)
  • Ocean City Beach (9.9 mi / 16 km)
  • Northside Park (7.3 mi / 11.8 km)
  • Fenwick Island Beach (8.8 mi / 14.2 km)
  • Bethany Beach Beaches (9.8 mi / 15.7 km)
  • Inlet Park (9.9 mi / 15.9 km)

Travelling to and around Bishopville

Fly into Ocean City, MD (OCE-Ocean City Municipal), the closest airport, located 10 mi (16.1 km) from the city centre. If you can't find a flight that's convenient for your trip, you could book a flight to Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional), which is 18.8 mi (30.3 km) away.

Frequently asked questions

Where are the best areas for renting a beach house in Bishopville?
For renting a beach house in Bishopville, Maryland, the nearby coastal areas of Ocean City and Fenwick Island are excellent choices. Ocean City, just a short drive away, is well-known for its vibrant boardwalk, sandy beaches, and numerous recreational activities. Here, holiday rentals often come with amenities such as oceanfront balconies, private pools, and fully equipped kitchens, superb for families or groups looking to enjoy a beach getaway. Many properties also offer convenient access to local attractions, dining, and nightlife.In Fenwick Island, you can find a more tranquil atmosphere, with beach houses that typically feature spacious decks, outdoor grills, and easy access to quieter stretches of the beach. This area is ideal for those seeking a relaxing retreat, while still being close enough to the lively energy of Ocean City. Properties in Fenwick may also include amenities like beach gear rentals and community pools, enhancing the overall experience.Additionally, the Assawoman Bay nearby offers opportunities for water sports, fishing, and kayaking, with holiday rentals often positioned to take advantage of scenic views.
What is the most popular type of holiday rental accomodation in Bishopville?
In Bishopville, holiday houses are the most popular type of holiday rental, with several available in the area. These properties typically offer spacious living arrangements, including multiple bedrooms, fully equipped kitchens, and outdoor amenities such as patios or decks where guests can enjoy the serene surroundings. Additionally, there are several campsites in the vicinity, providing a more rustic experience for those looking to immerse themselves in nature.
Are there any family house rentals in Bishopville?
In Bishopville, Maryland, there are several family-friendly house rentals available, making it a great choice for those travelling with children. The area is known for its peaceful surroundings and proximity to natural attractions. Many properties offer spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play and explore. Visitors can expect amenities such as Wi-Fi, air conditioning, and sometimes even access to yards or decks for enjoying the fresh air.Nearby, families can discover the scenic beauty of Assateague Island, famous for its wild horses and stunning beaches, great for a day of sun and sand. Additionally, the local area is close to various parks and recreational activities, ensuring that there are plenty of options for outdoor fun.
Can I rent a holiday home with a pool or hot tub in Bishopville?
In Bishopville, Maryland, there are several holiday homes available for rent that feature pools or hot tubs. This quaint town, situated close to the beautiful beaches of the Delmarva Peninsula, offers a serene environment for travellers seeking relaxation. Many of the properties include amenities such as private outdoor pools, hot tubs, spacious patios, and fully equipped kitchens, making them superb for families or groups looking to unwind and enjoy time together.
Are there pet-friendly house rentals in Bishopville?
In Bishopville, there are several pet-friendly house rentals available, providing a welcoming environment for travellers with furry companions. Many of these homes come equipped with amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, ensuring a pleasant stay for both guests and their pets.The area is conveniently located near Assateague Island National Seashore, which offers opportunities for outdoor activities with pets, including walking along scenic trails and enjoying the beautiful beaches. Additionally, the nearby town of Ocean City provides further options for pet-friendly dining and shopping, enhancing the overall experience for visitors.
Are there any remote work holiday rentals in Bishopville?
In Bishopville, Maryland, there are several remote work-friendly holiday rentals available. This charming area offers a tranquil setting for those looking to balance work and leisure. Many of the properties feature essential amenities such as reliable internet access through third-party services, ensuring a productive work environment. Additionally, guests can expect comfortable living spaces, fully equipped kitchens for convenient meal preparation, and outdoor areas for relaxation after a day of work. The proximity to local attractions, including the scenic Assateague Island and nearby beaches, provides ample opportunities for recreation and unwinding after hours. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Bishopville?
In Bishopville, popular rental amenities typically include onsite parking, which is convenient for guests with vehicles. Many properties feature an arcade game room, providing entertainment for families and groups. Travellers can also expect balconies in some rentals, offering a pleasant space to enjoy the outdoors. Additionally, the area has nearby casino locations, adding to the appeal for those looking for entertainment options. Many rentals also come equipped with coffee and tea makers, allowing guests to enjoy a warm beverage at their convenience.*You must be at least 18 years old to participate in gambling activities in the United Kingdom. Please gamble responsibly. If you feel that gambling is affecting your life, seek help from organisations such as BeGambleAware at www.begambleaware.org or call their helpline at 0808 8020 133.
When is the best time to visit Bishopville for a holiday rental?
The best time to visit Bishopville for a holiday rental is during the peak season from June to August, with July being the most popular month. This vibrant period attracts families and adventure seekers eager to embrace the warm weather and explore the natural beauty of Maryland's Eastern Shore. With temperatures typically ranging from 20 to 30 degrees Celsius, visitors can enjoy a variety of outdoor activities, from kayaking in the nearby Assawoman Bay to sunbathing on the area's beautiful beaches.In July, the atmosphere in Bishopville is particularly lively, as tourists flock to local festivals and events that showcase the region's rich culture and community spirit. The longer daylight hours provide ample opportunity for sightseeing and leisure activities, making it an ideal time for those looking to create memorable experiences with loved ones.For those seeking a more budget-friendly option, consider visiting in December. While this month falls outside the high season, it offers a unique charm, allowing for a quieter exploration of Bishopville's attractions and a chance to witness the area's festive holiday spirit without the crowds.
What are the top attractions in Bishopville?
In Bishopville, Maryland, visitors can explore a range of attractions that highlight the area's natural beauty and local culture. The famous and quirky "World's Largest Teapot" is a must-see landmark that draws attention from tourists. For nature enthusiasts, the nearby Assateague Island National Seashore offers stunning views of wild ponies, beautiful beaches, and opportunities for kayaking and birdwatching.In the heart of Bishopville, the Bishopville Heritage Society Museum provides insights into the town's history and local heritage, showcasing various artefacts and exhibits. Additionally, the surrounding areas feature picturesque landscapes great for hiking and exploring, making it an ideal spot for outdoor activities.
Are all fees included in the Bishopville holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Bishopville holiday homes with parking?
Stayz offers a wide selection of holiday homes in Bishopville with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Bishopville holiday homes?
You can find great discounts on holiday homes in Bishopville on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Bishopville holiday home booking on Stayz?
To find Bishopville holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Bishopville?
A long-stay holiday home in Bishopville is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Bishopville holiday home?
Book your Bishopville holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Bishopville?
Prices for holiday homes in Bishopville vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Bishopville to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.