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Pittsville Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Pittsville vacation 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
$231 nightly
The price is $248
Nov 10 - Nov 11
Total with taxes and fees
Salisbury Riverfront Lofts
An open door leading to a bedroom with a bed, a nightstand, and a lamp.

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.
$177 nightly
The price is $187
Oct 11 - Oct 12
Total with taxes and fees
Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown
A single-story house with a front porch, a door, and a mailbox.

3. 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.
$342 nightly
The price is $363
Oct 19 - Oct 20
Total with taxes and fees
Salisbury Hideaway
A wooden gazebo with a table and chairs, surrounded by plants and a grill.

4. 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)
"We loved Laurie's home! So comfortable and clean. There are so many great spots to sit both inside and out. The outdoor bar area is really fun, the beds comfortable, kitchen had all we needed. Our host comunicated to be sure we had no issues and was genuine and helpful. Its such a cute older home full of all conveniences we needed. Loved our stay!"
United States
Denise D.
BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen
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.
$207 nightly
The price is $232
Oct 18 - Oct 19
Total with taxes and fees
On Main Street - Apartment C - Berlin, MD
A gym with treadmills, dumbbells, and exercise balls, large windows with a view of the ocean.

6. 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
$88 nightly
The price is $99
Oct 14 - Oct 15
Total with taxes and fees
Coconut Malorie Resort Ocean City, an Ascend Collection Hotel
A living room with a dining area, a TV mounted on the wall, and a ceiling light fixture.

7. 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.
$335 nightly
The price is $355
Oct 19 - Oct 20
Total with taxes and fees
Salisbury Cottage
A living room with a ceiling fan, a round coffee table, and two sofas.

8. Dagsboro Retreat

Dagsboro Retreat
2.0 star property
Dagsboro
10.0 out of 10, Exceptional, (1 review)
"I loved it"
United States
Alexandra
$265 nightly
The price is $265
Nov 1 - Nov 2
Total with taxes and fees
Dagsboro Retreat
A covered patio with a table and chairs, overlooking a beach.

9. 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
$83 nightly
The price is $93
Oct 11 - Oct 12
Total with taxes and fees
Majestic Hotel & Apartments
A compact kitchen with a checkered floor, a dining table with chairs, and a large wall art piece.

10. 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.
$179 nightly
The price is $189
Oct 11 - Oct 12
Total with taxes and fees
Retro Hipster: Close to downtown, dining and fun
A house surrounded by dense trees and a wooden dock extending into a body of water.

11. 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.
$384 nightly
The price is $430
Nov 9 - Nov 10
Total with taxes and fees
Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!
A large outdoor swimming pool with people swimming and lounging, surrounded by a fence and shaded areas.

12. 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
$326 nightly
The price is $365
Oct 12 - Oct 13
Total with taxes and fees
Comfortable cottage in gated community, 5 mins to OC and Assateague
A two-story house with a front porch, a driveway, and a landscaped garden with various plants and a small tree.

13. 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)
"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
$212 nightly
The price is $216
Oct 21 - Oct 22
Total with taxes and fees
EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!
A covered porch with wooden flooring, white railings, and two green chairs.

14. Wilmington Terrace

Wilmington Terrace
3.0 star property
Downtown Ocean City
8.2 out of 10, Very good, (12 reviews)
"The staff was very friendly, the apartment was very clean, I love that pets are welcome and the beach and boardwalk are less than 2 minutes walk. EXCELLENT!"
United States
Jennifer
$188 nightly
The price is $211
Oct 11 - Oct 12
Total with taxes and fees
Wilmington Terrace
A room with a bed, a chair, a table, and a potted plant.

15. 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.
$393 nightly
The price is $440
Nov 9 - Nov 10
Total with taxes and fees
Ocean Pines Retreat with Beach Club
A living room with a patterned rug, a bookshelf, a red sofa, and a fish-shaped wall decoration.

16. 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.
$219 nightly
The price is $229
Oct 11 - Oct 12
Total with taxes and fees
Spacious Riverfront Loft Close to Downtown and Dining
A marina with boats docked, wooden chairs on a deck, and houses in the background.

17. 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
$657 nightly
The price is $736
Oct 12 - Oct 13
Total with taxes and fees
Charming 4-bedroom Beach House in Ocean Pines
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.

18. 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.
$203 nightly
The price is $227
Oct 18 - Oct 19
Total with taxes and fees
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.

19. Game Room! Waterfront Group Haven in Ocean Pines

Game Room! Waterfront Group Haven in Ocean Pines
3.0 star property
Ocean Pines
$923 nightly
The price is $1,034
Oct 18 - Oct 19
Total with taxes and fees
Game Room! Waterfront Group Haven in Ocean Pines
A living room with a sofa, a lamp, a TV, and a view of the sea through a balcony.

20. Beach Paradise IV-Downtown Waterfront, Top Floor, Luxury Penthouse Condo

Beach Paradise IV-Downtown Waterfront, Top Floor, Luxury Penthouse Condo
Downtown Ocean City
9.8 out of 10, Exceptional, (88 reviews)
"Beautiful condo, we had a really nice time and want to come back again!!"
United States
Lisa K.
$306 nightly
The price is $343
Nov 1 - Nov 2
Total with taxes and fees
Beach Paradise IV-Downtown Waterfront, Top Floor, Luxury Penthouse Condo
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

Everything you need to know about Pittsville vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pittsville vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Pittsville vacation 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 low season months. For more hustle and bustle, you may prefer to visit Pittsville in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $88 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Pittsville rentals

At Expedia, we put the best Pittsville vacation 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 vacation.

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 vacation rentals in Pittsville?

Yes, we have vacation rentals near top local attractions in Pittsville, or you can go with a more remote option if you'd like a relaxing place to stay.

What are some of the best vacation rentals in Pittsville?

Quiet Beachfront Retreat with Private Balcony: This vacation home near 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 larger area.

What are vacation rentals like in Pittsville?

Vacation rentals are private properties you can stay in for a short or long stay in Pittsville. Vacation rentals offer extras like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, a vacation rental can provide a sense of security away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for a small group gathering.