A sunset over a calm lake with a bridge and silhouetted trees.

Bishopville Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Bishopville vacation rentals

A modern bedroom with a large bed, a TV, and a ceiling fan.

1. Coconut Malorie Resort Ocean City, an Ascend Collection Hotel

Coconut Malorie Resort Ocean City, an Ascend Collection Hotel
3.0 star property
Midtown Ocean City
7.4 out of 10, Good, (1,328 reviews)
"Our room.seemed to be all new and we loved how there was a separate living room and bedroom with privacy doors. We had a beautiful view of the bay too from the second floor and we loved being on the sunset side of OC:)"
United States
cara
The price is ￥14,721
￥16,489 total
includes taxes & fees
Oct 13 - Oct 14
Coconut Malorie Resort Ocean City, an Ascend Collection Hotel
A room with a bed, a chair, a table, and a potted plant.

2. Ocean Pines Retreat with Beach Club

Ocean Pines Retreat with Beach Club
Ocean Pines
10.0 out of 10, Exceptional, (46 reviews)
"This is our family's second year staying here and we loved it just as much!"
United States
Ashleigh N.
The price is ￥31,662
￥70,746 total
includes taxes & fees
Nov 11 - Nov 12
Ocean Pines Retreat with Beach Club
A dining area with a wooden table and white chairs, a sofa, and a television in the background.

3. Mallard Lakes Waterfront Beach Condo in Fenwick Island with Two Pools

Mallard Lakes Waterfront Beach Condo in Fenwick Island with Two Pools
Selbyville
9.8 out of 10, Exceptional, (50 reviews)
"Ideal location and very nice accommodations!"
United States
Jeff A.
The price is ￥19,235
￥46,855 total
includes taxes & fees
Oct 14 - Oct 15
Mallard Lakes Waterfront Beach Condo in Fenwick Island with Two Pools
A modern kitchen with white cabinetry, a central island with bar stools, stainless steel appliances, and a large window providing natural light.

4. Keen-Wik on the bay | Balcony | House

Keen-Wik on the bay | Balcony | House
Keen-Wik On the Bay
9.0 out of 10, Wonderful, (13 reviews)
"Some of the beds were unteneable and really ruined the experience for a few of us. Also the grease tray on the grill never gets cleaned and grease is dripping on the patio below and was unpleasant. Replace the bed slats and focus on keeping the grill from dripping grease and I'd give it 5 stars with how nice everything else was considering the price. Staff was also very responsive and professional but there wasn't anything they could do about the bed situation."
United States
Sean K.
Keen-Wik on the bay | Balcony | House
A wooden deck with a pool, large windows, and a view of residential buildings.

5. Beds Made, Christmas Tree, 2 Fireplaces, Well-Stocked Kitchen & Resort Amenities

Beds Made, Christmas Tree, 2 Fireplaces, Well-Stocked Kitchen & Resort Amenities
Selbyville
10.0 out of 10, Exceptional, (36 reviews)
"Great hospitality, location, and vibe."
United States
Brittany S.
The price is ￥48,991
￥121,486 total
includes taxes & fees
Oct 13 - Oct 14
Beds Made, Christmas Tree, 2 Fireplaces, Well-Stocked Kitchen & Resort Amenities
A wooden deck with a white railing, a bench, and a view of neighboring houses.

6. Walk to Maryland Beach: Coastal Condo w/ Balcony

Walk to Maryland Beach: Coastal Condo w/ Balcony
North Ocean City
9.8 out of 10, Exceptional, (13 reviews)
"Clean"
United States
Denise G.
The price is ￥26,121
￥77,483 total
includes taxes & fees
Oct 13 - Oct 14
Walk to Maryland Beach: Coastal Condo w/ Balcony
A balcony with two chairs and a table, overlooking a beach with the ocean and a clear sky.

7. #1 Rated Condo, Oceanfront, with Bay View Too

#1 Rated Condo, Oceanfront, with Bay View Too
North Ocean City
10.0 out of 10, Exceptional, (342 reviews)
"Had a great stay "
United States
Ed B.
The price is ￥7,757
￥35,993 total
includes taxes & fees
Oct 27 - Oct 28
#1 Rated Condo, Oceanfront, with Bay View Too
A spacious living area with a large window overlooking a body of water, a fireplace, and a modern staircase.

8. Game Room! Waterfront Group Haven in Ocean Pines

Game Room! Waterfront Group Haven in Ocean Pines
Ocean Pines
10.0 out of 10, Exceptional, (9 reviews)
"Beautiful views, quiet neighborhood close to the beach. "
United States
James C.
The price is ￥57,625
￥167,555 total
includes taxes & fees
Oct 18 - Oct 19
Game Room! Waterfront Group Haven in Ocean Pines
A room with teal walls, a gray sofa, a white dresser, and a ceiling fan.

9. Beach Days & Bay Sunsets. Your Easy OCMD Escape! Raffles Unit 339 N

Beach Days & Bay Sunsets. Your Easy OCMD Escape! Raffles Unit 339 N
North Ocean City
9.2 out of 10, Wonderful, (54 reviews)
"check in/check out were super simple. place was clean, but a little tight for 5. location is great."
United States
Theodore B.
The price is ￥9,974
￥33,157 total
includes taxes & fees
Oct 13 - Oct 14
Beach Days & Bay Sunsets. Your Easy OCMD Escape! Raffles Unit 339 N
A beach with waves crashing onto the shore, a wooden fence, and dense green vegetation in the foreground.

10. Delightful Escape, Oceanfront 2BDR , Awesome Views, Pool, Clean!

Delightful Escape, Oceanfront 2BDR , Awesome Views, Pool, Clean!
North Ocean City
10.0 out of 10, Exceptional, (115 reviews)
"The beach view is perfect, the space is beautifully decorated and clean. We loved it!"
United States
Nancy U.
The price is ￥24,934
￥59,309 total
includes taxes & fees
Nov 1 - Nov 2
Delightful Escape, Oceanfront 2BDR , Awesome Views, Pool, Clean!
A marina with boats docked, wooden chairs on a deck, and houses in the background.

11. Charming 4-bedroom Beach House in Ocean Pines

Charming 4-bedroom Beach House in Ocean Pines
Ocean Pines
9.8 out of 10, Exceptional, (18 reviews)
"The house was so nice! Highly recommend this property"
United States
Anonymous traveler
The price is ￥60,949
￥115,604 total
includes taxes & fees
Oct 13 - Oct 14
Charming 4-bedroom Beach House in Ocean Pines
A balcony with wicker furniture overlooking the ocean.

12. Top-Rated Luxury Oceanfrt Condo Spectacular Views-Outstanding Reviews

Top-Rated Luxury Oceanfrt Condo Spectacular Views-Outstanding Reviews
North Ocean City
9.6 out of 10, Exceptional, (113 reviews)
"The view of the ocean and beach is fantastic. And you can see the bayside as well. The whole place was so clean and so well kept. Pool area was beautiful."
United States
Jay channel R.
The price is ￥15,673
￥74,647 total
includes taxes & fees
Nov 1 - Nov 2
Top-Rated Luxury Oceanfrt Condo Spectacular Views-Outstanding Reviews
A spacious living area with a large window overlooking a body of water, a fireplace, and a modern staircase.

13. Game Room! Waterfront Group Haven in Ocean Pines

Game Room! Waterfront Group Haven in Ocean Pines
3.0 star property
Ocean Pines
The price is ￥68,707
￥163,712 total
includes taxes & fees
Oct 18 - Oct 19
Game Room! Waterfront Group Haven in Ocean Pines
A balcony with a table and chairs, overlooking a body of water during sunset.

14. BeachBox V • 5th-Floor Oceanfront • Expansive View • Beachfront Bliss

BeachBox V • 5th-Floor Oceanfront • Expansive View • Beachfront Bliss
North Ocean City
10.0 out of 10, Exceptional, (8 reviews)
"We truly enjoyed our stay. The place was very clean with an amazing view. Excellent communication with the owners. The check in process was very smooth. "
United States
Natasha H.
The price is ￥19,358
￥51,191 total
includes taxes & fees
Oct 31 - Nov 1
BeachBox V • 5th-Floor Oceanfront • Expansive View • Beachfront Bliss
A beachside boardwalk with shops, a Ferris wheel, and a tram.

15. On Main Street - Apartment C - Berlin, MD

On Main Street - Apartment C - Berlin, MD
Downtown Berlin
9.4 out of 10, Exceptional, (43 reviews)
"A perfect location if you want to explore downtown Berlin. It’s right in the heart of Main Street walking distance to everything.The apartment had everything we needed and was very cozy and clean . Would definitely book this spot again."
United States
Sarah V.
The price is ￥11,398
￥36,702 total
includes taxes & fees
Oct 18 - Oct 19
On Main Street - Apartment C - Berlin, MD
A stainless steel kitchen sink with a modern faucet, a bottle of dish soap, and a knife block on the countertop.

16. Dog Friendly: Pool, Game Room, Near Bethany Beach

Dog Friendly: Pool, Game Room, Near Bethany Beach
Dagsboro
The price is ￥24,538
￥85,168 total
includes taxes & fees
Oct 13 - Oct 14
Dog Friendly: Pool, Game Room, Near Bethany Beach
A multi-story building with a white exterior, balconies, and a sign indicating it is an apartment complex.

17. Ocean Terrace Family Apartments

Ocean Terrace Family Apartments
3.0 star property
Downtown Ocean City
7.6 out of 10, Good, (66 reviews)
"There isn’t a lot if parking for the property but besides that it was great"
United States
Pamela
The price is ￥9,004
￥10,084 total
includes taxes & fees
Oct 13 - Oct 14
Ocean Terrace Family Apartments
A modern kitchen with wooden cabinets, a dining area set for six, and a large window providing natural light.

18. BEACH PARADISE V - 4BR, 3.5BA NEW GARAGE Townhouse in PRIME MIDTOWN OC!

BEACH PARADISE V - 4BR, 3.5BA NEW GARAGE Townhouse in PRIME MIDTOWN OC!
North Ocean City
9.8 out of 10, Exceptional, (81 reviews)
"Very nice stay"
United States
Emma W.
The price is ￥30,870
￥79,079 total
includes taxes & fees
Oct 30 - Oct 31
BEACH PARADISE V - 4BR, 3.5BA NEW GARAGE Townhouse in PRIME MIDTOWN OC!
A wide beach with people and umbrellas, a lifeguard tower, and buildings in the background.

19. Completely Renovated Perfect Beachtown Escape for the Whole Family

Completely Renovated Perfect Beachtown Escape for the Whole Family
North Ocean City
9.4 out of 10, Exceptional, (28 reviews)
"Everything was clean and easy for a quick weekend stay. The location was super easy to get to and parking was a breeze. The short walk to the beach was perfect. Will be back again for sure. "
United States
Jamie S.
The price is ￥18,839
￥53,370 total
includes taxes & fees
Nov 1 - Nov 2
Completely Renovated Perfect Beachtown Escape for the Whole Family
A living room with a sofa, armchair, TV, and a table with a lamp.

20. ⛱️2BR/2BA OCEANFRONT BUILDING. Book End of Summer/FALL Rates AS LOW AS $99/Night

⛱️2BR/2BA OCEANFRONT BUILDING. Book End of Summer/FALL Rates AS LOW AS $99/Night
North Ocean City
10.0 out of 10, Exceptional, (145 reviews)
"Everything is very nice and clean."
United States
Paula H.
The price is ￥17,256
￥68,441 total
includes taxes & fees
Oct 13 - Oct 14
⛱️2BR/2BA OCEANFRONT BUILDING. Book End of Summer/FALL Rates AS LOW AS $99/Night
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Bishopville Hotel Reviews

Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

10/10 Excellent
"Several family members stayed here for a wedding in the area. Our suites were very nice. The full size refrigerator and even the stove came in very handy. The living area, bathroom and bedroom were roomy and comfortable. Would definitely stay here again."
Allison 3-night trip
Posted 2 hours ago
Princess Royale Oceanfront Resort

Find out more about Bishopville

Search for holiday rentals in Bishopville on Expedia! You can easily find your home rentals, villas, holiday apartments in Bishopville using one of the methods below:

  • View our selection of featured holiday rentals in Bishopville
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  • Enter your travel dates to view the best deals on holiday rentals in Bishopville while they last

Look no further and take a look at our great range of rental properties in Bishopville!

Frequently asked questions

Are there vacation rentals in Bishopville?

Yes, there are vacation rentals near the most popular sights in Bishopville, or you can select a secluded option if you're looking for a relaxing stay. Bishopville is known for its waterfront and golf courses.

What's the top vacation rental that Bishopville has to offer?

Quiet Beachfront Retreat with Private Balcony: This vacation home rental outside of Bishopville is located by the ocean and has a balcony, a selection of books, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals will I find in Bishopville?

Choose from 3 Expedia vacation rentals in Bishopville for a memorable vacation.

What’s there to see and do in Bishopville?

Assawoman Bay and Isle of Wight Bay are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find The Links at Lighthouse Sound and Ocean City Beach.

What’s a vacation rental in Bishopville like?

Vacation rentals are private properties you can book for a few weeks or just a few days in Bishopville. Vacation rentals feature extras like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for a small group gathering.