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

Bishopville Holiday Rentals

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Our top choices for Bishopville holiday 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, (1,327 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 NZ$176
includes taxes & fees
13 Oct - 14 Oct
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, (45 reviews)
"This is our family's second year staying here and we loved it just as much!"
United States
Ashleigh N.
The price is NZ$778
includes taxes & fees
9 Nov - 10 Nov
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 NZ$534
includes taxes & fees
14 Oct - 15 Oct
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 NZ$1,340
includes taxes & fees
12 Oct - 13 Oct
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 NZ$836
includes taxes & fees
11 Oct - 12 Oct
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, (342 reviews)
"Had a great stay "
United States
Ed B.
The price is NZ$395
includes taxes & fees
26 Oct - 27 Oct
#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 NZ$1,835
includes taxes & fees
18 Oct - 19 Oct
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 NZ$367
includes taxes & fees
12 Oct - 13 Oct
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 NZ$655
includes taxes & fees
1 Nov - 2 Nov
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 NZ$1,265
includes taxes & fees
12 Oct - 13 Oct
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 NZ$838
includes taxes & fees
1 Nov - 2 Nov
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 NZ$1,842
includes taxes & fees
18 Oct - 19 Oct
Game Room! Waterfront Group Haven in Ocean Pines

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

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 NZ$405
includes taxes & fees
18 Oct - 19 Oct
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 NZ$949
includes taxes & fees
11 Oct - 12 Oct
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, (64 reviews)
"There isn’t a lot if parking for the property but besides that it was great"
United States
Pamela
The price is NZ$142
includes taxes & fees
11 Oct - 12 Oct
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, (81 reviews)
"Very nice stay"
United States
Emma W.
The price is NZ$888
includes taxes & fees
30 Oct - 31 Oct
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 NZ$614
includes taxes & fees
4 Nov - 5 Nov
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 NZ$746
includes taxes & fees
13 Oct - 14 Oct
⛱️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 holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Bishopville holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Bishopville. 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 Bishopville. 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 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 holiday 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 Bishopville short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Bishopville?

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

What are some of the best holiday rentals that Bishopville has to offer?

Quiet Beachfront Retreat with Private Balcony: This holiday 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 holiday rentals will I find in Bishopville?

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

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 wider area, you’ll find The Links at Lighthouse Sound and Ocean City Beach.

What’s a holiday rental in Bishopville like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Bishopville. Holiday rentals feature amenities like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for family trips.