Bishopville holiday rentals

We found 8,409 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:1 Jan - 8 Jan

Upstairs kitchen/dinete
Terrace/patio
Upstairs living room
Upstairs sunroom
Exceptional
(73 reviews)

FAIRWAY TO HEAVEN: GOLF course views and BEACH parking pass

Berlin

5% off
AU$2,296
for 7 nights, 1 apartment
AU$328 per night
includes taxes & fees
FAIRWAY TO HEAVEN: GOLF course views and BEACH parking pass
Exterior
Property grounds
Private kitchen
Room
Exceptional
(108 reviews)

Huge Direct Oceanfront Townhouse with Beautiful Sunrises

Ocean City

7% off
AU$3,438
for 7 nights, 1 home
AU$491 per night
includes taxes & fees
Huge Direct Oceanfront Townhouse with Beautiful Sunrises
breakfast bar
Outdoor dining
Room
Sunny TV den/sunroom
Exceptional
(65 reviews)

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

Bethany Beach

8% off
AU$3,630
for 7 nights, 1 home
AU$519 per night
includes taxes & fees
Gorgeous Bethany retreat! Dog friendly, 4 BR/3BA, near trails, <2 miles to beach
Terrace/patio
Dining
Exterior
Living area
Exceptional
(62 reviews)

ONLY A 7 MINUTE WALK TO THE BEACH!

Bethany Beach

8% off
AU$7,014
for 7 nights, 1 home
AU$1,002 per night
includes taxes & fees
ONLY A 7 MINUTE WALK TO THE BEACH!
Interior
Interior
Property grounds
Exceptional
(67 reviews)

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

Ocean City

8% off
AU$2,768
for 7 nights, 1 apartment
AU$395 per night
includes taxes & fees
Beachfront living near Seacrets! Don't let this memorable getaway pass you by.
Living area
Exterior
Private kitchen
Interior
Exceptional
(93 reviews)

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

Ocean City

8% off
AU$3,528
for 7 nights, 1 apartment
AU$504 per night
includes taxes & fees
Great Location for your vacation. Very Pet Friendly!. Close to Boardwalk/Beach.
Dining
Dining
Exterior
Private kitchen
Exceptional
(16 reviews)

LAST DATES! Bay Sunset Getaway • Pool • 2BR/2BA • Free Linens

Ocean City

8% off
AU$5,152
for 7 nights, 1 apartment
AU$736 per night
includes taxes & fees
LAST DATES! Bay Sunset Getaway • Pool • 2BR/2BA • Free Linens
All new kitchen, granite counters, K-cup coffeemaker (not pictured)
If you're not familiar with Sea Colony, check out seacolony.com
Comfortable and sunny living room
Great view of the Swan Pond
Exceptional
(169 reviews)

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

Bethany Beach

8% off
AU$1,877
for 7 nights, 1 apartment
AU$268 per night
includes taxes & fees
Sea Colony, Walk to Beach & Tennis--Beautiful, Sparkling Clean Getaway!
Private kitchen
Designer Kitchen
Fully Equipped Kitchen
Private kitchen
Exceptional
(149 reviews)

Sea Colony. Ocean Front Condo 3 Bedroom New designer kitchen and baths

Bethany Beach

6% off
AU$3,000
for 7 nights, 1 apartment
AU$429 per night
includes taxes & fees
Sea Colony. Ocean Front Condo 3 Bedroom New designer kitchen and baths
05-1Q7A4356
Living area
ext+deck+vfne
KT+vfw
Exceptional
(8 reviews)

Biscayne Bungalow– Coastal Charm Near the Beach

Ocean City

5% off
AU$3,194
for 7 nights, 1 home
AU$456 per night
includes taxes & fees
Biscayne Bungalow– Coastal Charm Near the Beach
Beach
Living area
Living area
Pool
Exceptional
(58 reviews)

Beautiful Beachfront 2 Level Penthouse w 2 balconies! Full Ocean Views SLEEPS 7!

Ocean City

7% off
AU$7,926
for 7 nights, 1 apartment
AU$1,132 per night
includes taxes & fees
Beautiful Beachfront 2 Level Penthouse w 2 balconies! Full Ocean Views SLEEPS 7!
Relax, Have dinner, Play games, see the ocean!
view from balcony to living area
Breathtaking nighttime view from the condo
Ocean Front view of the Pyramid the most unique building on the beach
Exceptional
(102 reviews)

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

Ocean City

7% off
AU$1,944
for 7 nights, 1 apartment
AU$278 per night
includes taxes & fees
Escape to The Ocean! , Ocean Front, Beautiful View, Pool!
Large Back Deck
Living area
Holts Landing State Park Playground
House Front
Exceptional
(12 reviews)

Relaxing Retreat – Pet Friendly, Kayak & Canoe Included, Near Bethany Beach

Dagsboro

8% off
AU$3,036
for 7 nights, 1 home
AU$434 per night
includes taxes & fees
Relaxing Retreat – Pet Friendly, Kayak & Canoe Included, Near Bethany Beach
Indoor Pool (Open Summer months Only)
Winter is a Great Time to Enjoy the Beach!
Private kitchen
Bedroom with Two Full-Size Beds & Flat-Screen HDTV
Exceptional
(31 reviews)

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

Ocean City

6% off
AU$5,971
for 7 nights, 1 apartment
AU$853 per night
includes taxes & fees
Direct Ocean Front...In The Middle of it All!!!
Room
Pool
Sports court
Interior
Exceptional
(6 reviews)

2BR Condo,Pools & Walk to Beach

Ocean City

8% off
AU$3,131
for 7 nights, 1 apartment
AU$447 per night
includes taxes & fees
2BR Condo,Pools & Walk to Beach
45-1Q7A8892
32-1Q7A8831
40-1Q7A8864
43-1Q7A8882
Exceptional
(7 reviews)

Sunkissed Ocean Haven

Ocean City

6% off
AU$5,025
for 7 nights, 1 apartment
AU$718 per night
includes taxes & fees
Sunkissed Ocean Haven
Private kitchen
Exterior
Interior
Room
Exceptional
(86 reviews)

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

Ocean City

8% off
AU$3,528
for 7 nights, 1 apartment
AU$504 per night
includes taxes & fees
Great Location for your vacation. Very Pet Friendly!. Close to Boardwalk/Beach.
Private kitchen
Living area
Dining
Dining
Exceptional
(58 reviews)

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

Ocean City

7% off
AU$2,170
for 7 nights, 1 apartment
AU$310 per night
includes taxes & fees
No need to look any further for a one bedroom in OC. Long term rates available.
Living area
Room
Dining
Exterior
Exceptional
(47 reviews)

V73 - Beautiful 3BR/2BA Ocean View! Pet-Friendly! Just one bldg from the beach!

Ocean City

7% off
AU$2,499
for 7 nights, 1 apartment
AU$357 per night
includes taxes & fees
V73 - Beautiful 3BR/2BA Ocean View! Pet-Friendly! Just one bldg from the beach!
Dining
Exterior detail
Room
Interior
Excellent
(56 reviews)

3 bedroom Oceanside condo

Ocean City

11% off
AU$1,783
for 7 nights, 1 apartment
AU$255 per night
includes taxes & fees
3 bedroom Oceanside condo
Dock for crabbing or watching wildlife
Interior
Interior
Private kitchen
Exceptional
(102 reviews)

Stay at Heron Cove located in popular Mallard Lakes!

Selbyville

9% off
AU$935
for 7 nights, 1 apartment
AU$134 per night
includes taxes & fees
Stay at Heron Cove located in popular Mallard Lakes!
Dining
Beach
Interior
Private kitchen
Exceptional
(34 reviews)

Beautiful Direct Beach Front and Bayside View Condo with POOL!!

Ocean City

7% off
AU$2,204
for 7 nights, 1 apartment
AU$315 per night
includes taxes & fees
Beautiful Direct Beach Front and Bayside View Condo with POOL!!
Atrium
Living area
Kitchen
Indoor Pool and hot tub
Exceptional
(106 reviews)

Direct Oceanfront Condo on 11th Floor with Amazing views of Ocean and Bay

Ocean City

8% off
AU$5,841
for 7 nights, 1 apartment
AU$834 per night
includes taxes & fees
Direct Oceanfront Condo on 11th Floor with Amazing views of Ocean and Bay
South view of Boardwalk, Inlet and beach from balcony
View of condo from the beach !
Master Bedroom, king size bed
Pool
Exceptional
(121 reviews)

Ocean Front Condo on the Boardwalk

Ocean City

8% off
AU$2,535
for 7 nights, 1 apartment
AU$362 per night
includes taxes & fees
Ocean Front Condo on the Boardwalk

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

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    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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. 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:

  • Ocean City Beach (9.9 mi / 16 km)
  • Northside Park (7.3 mi / 11.8 km)
  • Maryland Beach (7.8 mi / 12.5 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.