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Pittsville Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Pittsville holiday rentals

A room with a large bed, multiple windows, and a ceiling fan.

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 AU$348
includes taxes & fees
27 Oct - 28 Oct
Salisbury Riverfront Lofts
A single-story house with a front porch, a door, and a mailbox.

2. Salisbury Hideaway

Salisbury Hideaway
Salisbury
10.0 out of 10, Exceptional, (23 reviews)
"Perfect for our weekend away watching college softball!!!"
United States
Michelle S.
The price is AU$454
includes taxes & fees
28 Sept - 29 Sept
Salisbury Hideaway
An open door leading to a bedroom with a bed, a nightstand, and a lamp.

3. 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 AU$259
includes taxes & fees
28 Sept - 29 Sept
Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown
A living room with a dining area, a TV mounted on the wall, and a ceiling light fixture.

4. 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 AU$490
includes taxes & fees
27 Oct - 28 Oct
Salisbury Cottage
A beachside boardwalk with shops, a Ferris wheel, and a tram.

5. 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 AU$341
includes taxes & fees
7 Oct - 8 Oct
On Main Street - Apartment C - Berlin, MD
A living room with a sofa, ottoman, and a lamp. There is a television mounted on the wall and a window with blinds.

6. Pool + Bay Access! Home 13 Mi to Ocean City Beach

Pool + Bay Access! Home 13 Mi to Ocean City Beach
3.0 star property
Ocean Pines
The price is AU$610
includes taxes & fees
27 Sept - 28 Sept
Pool + Bay Access! Home 13 Mi to Ocean City Beach
A gym with treadmills, dumbbells, and exercise balls, large windows with a view of the ocean.

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, (1,323 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 AU$116
includes taxes & fees
17 Oct - 18 Oct
Coconut Malorie Resort Ocean City, an Ascend Collection Hotel
A compact kitchen with a checkered floor, a dining table with chairs, and a large wall art piece.

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 AU$267
includes taxes & fees
27 Sept - 28 Sept
Retro Hipster: Close to downtown, dining and fun
A wooden gazebo with a table and chairs, surrounded by plants and a grill.

9. BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen

BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen
Berlin
9.8 out of 10, Exceptional, (112 reviews)
"Great hosting by Laurie"
United States
Jim C.
The price is AU$536
includes taxes & fees
29 Sept - 30 Sept
BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen
A living room with a sectional sofa, a coffee table, a blue armchair, and a small side table.

10. "The Hive"-Downtown Berlin, 4 BR, Sleeps 8, 2 Bath

"The Hive"-Downtown Berlin, 4 BR, Sleeps 8, 2 Bath
Downtown Berlin
10.0 out of 10, Exceptional, (6 reviews)
"My friends and I were absolutely thrilled with this place! It is clean, spacious and perfectly located in a cute little town with shops and restaurants.We all said we could live ve here. Very homey and comfortable."
United States
Bonni R.
"The Hive"-Downtown Berlin, 4 BR, Sleeps 8, 2 Bath
A large outdoor swimming pool with people swimming and lounging, surrounded by a fence and shaded areas.

11. 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, (56 reviews)
"Convenient amenities at Assateague Point, easy access to Assateague Island and OCMD. Everything in the unit was clean, in proper working order, and we had everything we needed for our family with young children. Would definitely stay here again."
United States
Alexandra
The price is AU$514
includes taxes & fees
27 Sept - 28 Sept
Comfortable cottage in gated community, 5 mins to OC and Assateague
A round wooden table with a clear glass vase containing yellow roses, positioned near a window with a view of a street and parked cars.

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 AU$341
includes taxes & fees
5 Oct - 6 Oct
On Main Street - Apartment B - Berlin, MD
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
Ocean Pines
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful views, quiet neighborhood close to the beach. "
United States
James C.
The price is AU$1,722
includes taxes & fees
18 Oct - 19 Oct
Game Room! Waterfront Group Haven in Ocean Pines
A two-story house with a front porch, a driveway, and a landscaped garden with various plants and a small tree.

14. 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, (62 reviews)
"We stayed at this property for 6 nights, everything was exactly like the pictures and very clean. We were just far enough to many shopping areas and grocery stores. It was very quiet and peaceful. Ed and Cindy are amazing hosts, we will be returning next year!"
United States
Haileigh
The price is AU$291
includes taxes & fees
8 Oct - 9 Oct
EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!
A house surrounded by dense trees and a wooden dock extending into a body of water.

15. 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)
"This place was perfect. Beds were comfy, it had everything i needed in the kitchen, secluded enough to feel like you were alone with nature but close enough to drive to tourist attractions. Literally everything we we looking for. Added bonus was napping in the screened in porch."
United States
Jackie P.
The price is AU$650
includes taxes & fees
5 Oct - 6 Oct
Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!
A spacious living area with a large window overlooking a body of water, a fireplace, and a modern staircase.

16. 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 AU$1,713
includes taxes & fees
18 Oct - 19 Oct
Game Room! Waterfront Group Haven in Ocean Pines
A modern living room with a sofa, coffee table, dining table, and chairs. There is a TV mounted on the wall and artwork above the table.

17. BeachParadise107-OCEANVIEW Townhome-Steps to BEACH and BOARDWALK-LINENS INCLUDED

BeachParadise107-OCEANVIEW Townhome-Steps to BEACH and BOARDWALK-LINENS INCLUDED
Downtown Ocean City
10.0 out of 10, Exceptional, (4 reviews)
"The house was as listed, it was an enjoyable stay. Ann was easy to work with. Thanks VRBO."
United States
Anonymous traveller
The price is AU$476
includes taxes & fees
26 Oct - 27 Oct
BeachParadise107-OCEANVIEW Townhome-Steps to BEACH and BOARDWALK-LINENS INCLUDED
A compact living space with a kitchenette, a bed with orange bedding, a grey armchair, and a small round table.

18. Studio Charm w/ Deck, Fireplace & Fooseball!: Walk to Beach, Boardwalk & Dining!

Studio Charm w/ Deck, Fireplace & Fooseball!: Walk to Beach, Boardwalk & Dining!
Midtown Ocean City
9.8 out of 10, Exceptional, (18 reviews)
"Very friendly and helpful host! The room was lovely and very clean when we arrived. We would stay with this host again."
United States
Hannah
The price is AU$347
includes taxes & fees
27 Sept - 28 Sept
Studio Charm w/ Deck, Fireplace & Fooseball!: Walk to Beach, Boardwalk & Dining!
A dining area with a wooden table set for four, surrounded by wicker chairs.

19. "BEACH PARADISE II" 4-BR/3.5-BA Exquisite Townhouse with POOL & GARAGE

"BEACH PARADISE II" 4-BR/3.5-BA Exquisite Townhouse with POOL & GARAGE
North Ocean City
9.6 out of 10, Exceptional, (140 reviews)
"Great place to stay. There was plenty of room, easy access to close shopping."
United States
Rebecca D.
The price is AU$500
includes taxes & fees
4 Oct - 5 Oct
"BEACH PARADISE II" 4-BR/3.5-BA Exquisite Townhouse with POOL & GARAGE
A room with a bed, a chair, a table, and a potted plant.

20. 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 AU$600
includes taxes & fees
26 Oct - 27 Oct
Ocean Pines Retreat with Beach Club
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

Hyatt Place Ocean City / Oceanfront

Hyatt Place Ocean City / Oceanfront

8/10 Good
"Nice property right on the boardwalk. Staff was great and very helpful. Price was a little high for offseason but overall we were happy."
Gina 1-night trip
Posted 3 hours ago
Hyatt Place Ocean City / Oceanfront

Find out more about Pittsville

Everything you need to know about Pittsville holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Pittsville holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pittsville holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Pittsville holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pittsville. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pittsville holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pittsville holiday rentals we have selected for you start as low as AU$96 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Pittsville rentals

At Expedia, we put the best Pittsville holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Pittsville rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pittsville holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pittsville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.