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Pittsville Holiday Rentals

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Our top choices for Pittsville holiday rentals

1. Salisbury Riverfront Lofts

Salisbury Riverfront Lofts
3.0 star property
Salisbury
9.4 out of 10, Exceptional, (27 reviews)
"Excellent choice for the price, recommended for larger groups."
United States
Marcos
The price is NZ$441
includes taxes & fees
12 Nov - 13 Nov
Salisbury Riverfront Lofts

2. Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown

Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown
Salisbury
9.8 out of 10, Exceptional, (25 reviews)
"Great location with plenty of space to relax."
United States
Doug R.
The price is NZ$330
includes taxes & fees
18 Oct - 19 Oct
Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown

3. 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$409
includes taxes & fees
18 Oct - 19 Oct
On Main Street - Apartment C - Berlin, MD

4. Salisbury Hideaway

Salisbury Hideaway
Salisbury
10.0 out of 10, Exceptional, (24 reviews)
"Perfect for our weekend away watching college softball!!!"
United States
Michelle S.
The price is NZ$644
includes taxes & fees
13 Oct - 14 Oct
Salisbury Hideaway

5. Salisbury Cottage

Salisbury Cottage
Salisbury
10.0 out of 10, Exceptional, (40 reviews)
"Super convenient to campus and everything was clean and worked perfectly. Overall, a great stay and met all of our expectations."
United States
Matthew B.
The price is NZ$648
includes taxes & fees
3 Nov - 4 Nov
Salisbury Cottage

6. Cozy 2-bedroom bungalow, 10 minutes from beach, pet friendly

Cozy 2-bedroom bungalow, 10 minutes from beach, pet friendly
Berlin
9.8 out of 10, Exceptional, (48 reviews)
"Super clean, owner is beyond friendly and attentive, would definitely stay here again!"
United States
Andrea S.
Cozy 2-bedroom bungalow, 10 minutes from beach, pet friendly

7. 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 NZ$185
includes taxes & fees
13 Oct - 14 Oct
Coconut Malorie Resort Ocean City, an Ascend Collection Hotel

8. Retro Hipster: Close to downtown, dining and fun

Retro Hipster: Close to downtown, dining and fun
Salisbury
9.2 out of 10, Wonderful, (20 reviews)
"Great alternative to a hotel!"
United States
Courtney L.
The price is NZ$333
includes taxes & fees
28 Oct - 29 Oct
Retro Hipster: Close to downtown, dining and fun

9. Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!

Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!
Newark
10.0 out of 10, Exceptional, (20 reviews)
"Beautiful, clean, well appointed house in a peaceful setting. Easy & quick (20 minute) access to Assateague & Ocean City beaches without the chaos of staying in OC. Berlin and Snow Hill are fun historic eastern shore towns to explore. Take a day trip south to Pokomoke State Park for a calming non-beach nature experience. So nice we booked it again on our first day there."
United States
David M.
The price is NZ$773
includes taxes & fees
10 Nov - 11 Nov
Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!

10. EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!

EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!
Georgetown
9.8 out of 10, Exceptional, (63 reviews)
"The suite was very clean and our two children greatly enjoyed the pool!"
United States
Kay Lorelle R.
The price is NZ$374
includes taxes & fees
21 Oct - 22 Oct
EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!

11. 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 NZ$142
includes taxes & fees
13 Oct - 14 Oct
Ocean Terrace Family Apartments

12. On Main Street - Apartment B - Berlin, MD

On Main Street - Apartment B - Berlin, MD
Downtown Berlin
8.8 out of 10, Excellent, (47 reviews)
"Great location and the place was clean and spacious. Nice little surprise seeing the farmers market right out front Sunday morning."
United States
April M.
The price is NZ$409
includes taxes & fees
18 Oct - 19 Oct
On Main Street - Apartment B - Berlin, MD

13. Spacious Riverfront Loft Close to Downtown and Dining

Spacious Riverfront Loft Close to Downtown and Dining
Salisbury
9.0 out of 10, Wonderful, (13 reviews)
"Great location, great restaurants below the loft."
United States
Pamela F.
The price is NZ$395
includes taxes & fees
19 Oct - 20 Oct
Spacious Riverfront Loft Close to Downtown and Dining

14. Majestic Hotel & Apartments

Majestic Hotel & Apartments
2.0 star property
Downtown Ocean City
5.8 out of 10, (530 reviews)
"Very bice"
United States
Robert
The price is NZ$137
includes taxes & fees
13 Oct - 14 Oct
Majestic Hotel & Apartments

15. Getaway on 1/2 Acre w/ Deck in Georgetown

Getaway on 1/2 Acre w/ Deck in Georgetown
3.0 star property
Georgetown
10.0 out of 10, Exceptional, (1 review)
"This place is just as you see in the photos; clean, welcoming, great location, and very peaceful. We are certainly looking forward to staying here next year, if available. The contact person was available and answered quickly when I contacted him. "
United States
ANA
The price is NZ$594
includes taxes & fees
9 Nov - 10 Nov
Getaway on 1/2 Acre w/ Deck in Georgetown

16. Dagsboro Retreat

Dagsboro Retreat
2.0 star property
Dagsboro
10.0 out of 10, Exceptional, (1 review)
"I loved it"
United States
Alexandra
The price is NZ$425
includes taxes & fees
1 Nov - 2 Nov
Dagsboro Retreat

17. Monte Carlo Condos

Monte Carlo Condos
3.0 star property
Downtown Ocean City
7.0 out of 10, Good, (74 reviews)
"Unexpected pet fee on top of resort fees we did expect. Nice and close to boardwalk. Room was quiet, private, spacious."
United States
Ben
The price is NZ$380
includes taxes & fees
26 Oct - 27 Oct
Monte Carlo Condos

18. 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
13 Oct - 14 Oct
Dog Friendly: Pool, Game Room, Near Bethany Beach

19. Comfortable cottage in gated community, 5 mins to OC and Assateague

Comfortable cottage in gated community, 5 mins to OC and Assateague
Assateague Pointe
9.8 out of 10, Exceptional, (57 reviews)
"The cottage location is great for golf, less than 20 minutes ride to most courses. Also dining in Berlin is better than traffic to Oean City."
United States
Joe
The price is NZ$644
includes taxes & fees
13 Oct - 14 Oct
Comfortable cottage in gated community, 5 mins to OC and Assateague

20. 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
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 Pittsville Hotel Reviews

Find out more about Pittsville

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 Pittsville 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 Pittsville. 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 Pittsville. Seeing all the best attractions is bound to make you fall in love with Pittsville. 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 Pittsville short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Pittsville?

Yes, there are holiday rentals close to the most popular sights in Pittsville, or you can select a more secluded option if you're looking for a relaxing stay.

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

Quiet Beachfront Retreat with Private Balcony: This holiday home rental outside of Pittsville 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.

What can I see and do in Pittsville?

While exploring the area, visit family-friendly sights like Frontier Town Water Park and Golf, or get outside and enjoy nature at Ocean City Beach. Wicomico Youth and Civic Center and Henry S. Parker Athletic Complex are a couple of places you'll find in the wider area.

What are holiday rentals like in Pittsville?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pittsville. Holiday rentals feature extras like laundry facilities and kitchens so you'll feel just like you're staying in your own 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 reception areas while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for a family trip.