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

Bishopville Vacation Rentals

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Our top choices for Bishopville vacation rentals

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, (1,329 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 CA $134
CA $150 total
includes taxes & fees
Oct 14 - Oct 15
Coconut Malorie Resort Ocean City, an Ascend Collection Hotel

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 CA $300
CA $646 total
includes taxes & fees
Nov 3 - Nov 4
Ocean Pines Retreat with Beach Club

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 CA $173
CA $426 total
includes taxes & fees
Oct 15 - Oct 16
Mallard Lakes Waterfront Beach Condo in Fenwick Island with Two Pools

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

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 CA $442
CA $1,096 total
includes taxes & fees
Oct 15 - Oct 16
Beds Made, Christmas Tree, 2 Fireplaces, Well-Stocked Kitchen & Resort Amenities

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 CA $236
CA $696 total
includes taxes & fees
Oct 14 - Oct 15
Walk to Maryland Beach: Coastal Condo w/ Balcony

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, (343 reviews)
"Had a great stay "
United States
Ed B.
The price is CA $70
CA $326 total
includes taxes & fees
Nov 2 - Nov 3
#1 Rated Condo, Oceanfront, with Bay View Too

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 CA $484
CA $1,446 total
includes taxes & fees
Oct 18 - Oct 19
Game Room! Waterfront Group Haven in Ocean Pines

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 CA $90
CA $297 total
includes taxes & fees
Oct 22 - Oct 23
Beach Days & Bay Sunsets. Your Easy OCMD Escape! Raffles Unit 339 N

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 CA $225
CA $530 total
includes taxes & fees
Nov 1 - Nov 2
Delightful Escape, Oceanfront 2BDR , Awesome Views, Pool, Clean!

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 traveller
The price is CA $549
CA $1,049 total
includes taxes & fees
Oct 17 - Oct 18
Charming 4-bedroom Beach House in Ocean Pines

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 CA $141
CA $667 total
includes taxes & fees
Nov 1 - Nov 2
Top-Rated Luxury Oceanfrt Condo Spectacular Views-Outstanding Reviews

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 CA $580
CA $1,432 total
includes taxes & fees
Oct 18 - Oct 19
Game Room! Waterfront Group Haven in Ocean Pines

14. BeachBox® V • 5th-Floor Oceanfront • Expansive Views • East Winds 502

BeachBox® V • 5th-Floor Oceanfront • Expansive Views • East Winds 502
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 CA $175
CA $431 total
includes taxes & fees
Oct 31 - Nov 1
BeachBox® V • 5th-Floor Oceanfront • Expansive Views • East Winds 502

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 CA $103
CA $330 total
includes taxes & fees
Oct 18 - Oct 19
On Main Street - Apartment C - Berlin, MD

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

Dog Friendly: Pool, Game Room, Near Bethany Beach
Dagsboro
The price is CA $184
CA $680 total
includes taxes & fees
Oct 15 - Oct 16
Dog Friendly: Pool, Game Room, Near Bethany Beach

17. Ocean Terrace Family Apartments

Ocean Terrace Family Apartments
3.0 star property
Downtown Ocean City
7.6 out of 10, Good, (67 reviews)
"There isn’t a lot if parking for the property but besides that it was great"
United States
Pamela
The price is CA $81
CA $91 total
includes taxes & fees
Oct 15 - Oct 16
Ocean Terrace Family Apartments

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, (82 reviews)
"Very nice stay"
United States
Emma W.
The price is CA $279
CA $707 total
includes taxes & fees
Oct 30 - Oct 31
BEACH PARADISE V - 4BR, 3.5BA NEW GARAGE Townhouse in PRIME MIDTOWN OC!

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 CA $170
CA $498 total
includes taxes & fees
Nov 1 - Nov 2
Completely Renovated Perfect Beachtown Escape for the Whole Family

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 CA $156
CA $616 total
includes taxes & fees
Oct 14 - Oct 15
⛱️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

Find out more about Bishopville

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Bishopville. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.