Default HTG hotel image

Pittsville Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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, (28 reviews)
"Excellent choice for the price, recommended for larger groups."
United States
Marcos
$230 nightly
The price is $247
Nov 19 - Nov 20
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.
$175 nightly
The price is $185
Nov 8 - Nov 9
Total with taxes and fees
Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown
A gym with treadmills, dumbbells, and exercise balls, large windows with a view of the ocean.

3. 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, (1,330 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
$104 nightly
The price is $116
Oct 30 - Oct 31
Total with taxes and fees
Coconut Malorie Resort Ocean City, an Ascend Collection Hotel
A beachside boardwalk with shops, a Ferris wheel, and a tram.

4. On Main Street - Apartment C - Berlin, MD

On Main Street - Apartment C - Berlin, MD
Downtown Berlin
9.4 out of 10, Exceptional, (43 reviews)
"Had great mini vac . The vrbo was right down town lots great shops and good choices for meals. All ready thinking about going back"
United States
Jeffry C.
$207 nightly
The price is $231
Nov 3 - Nov 4
Total with taxes and fees
On Main Street - Apartment C - Berlin, MD
A single-story house with a front porch, a door, and a mailbox.

5. 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
Nov 17 - Nov 18
Total with taxes and fees
Salisbury Hideaway
A living room with a dining area, a TV mounted on the wall, and a ceiling light fixture.

6. 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.
$344 nightly
The price is $365
Nov 17 - Nov 18
Total with taxes and fees
Salisbury Cottage
A living room with a sofa, a lamp, a television, and a window with blinds.

7. Pet-Friendly Cottage on 1.5 Acres Near Beaches!

Pet-Friendly Cottage on 1.5 Acres Near Beaches!
Selbyville
$199 nightly
The price is $201
Oct 25 - Oct 26
Total with taxes and fees
Pet-Friendly Cottage on 1.5 Acres Near Beaches!
A covered patio with a table and chairs, overlooking a beach.

8. Majestic Hotel & Apartments

Majestic Hotel & Apartments
2.0 star property
Downtown Ocean City
5.8 out of 10, (531 reviews)
"Right in front of the board walk and almost center to everything"
United States
Wilber
$83 nightly
The price is $93
Oct 21 - Oct 22
Total with taxes and fees
Majestic Hotel & Apartments
A marina with boats docked, wooden chairs on a deck, and houses in the background.

9. Charming 4-bedroom Beach House in Ocean Pines

Charming 4-bedroom Beach House in Ocean Pines
Ocean Pines
9.8 out of 10, Exceptional, (19 reviews)
"The house was so nice! Highly recommend this property"
United States
Anonymous traveler
$657 nightly
The price is $736
Oct 21 - Oct 22
Total with taxes and fees
Charming 4-bedroom Beach House in Ocean Pines
A living room with a ceiling fan, a round coffee table, and two sofas.

10. 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 balcony with a view of a parking lot and buildings.

11. Americana Condos 10th street

Americana Condos 10th street
3.5 star property
Downtown Ocean City
8.6 out of 10, Excellent, (34 reviews)
"Wonderful views and so big!"
United States
Liz
$387 nightly
The price is $433
Nov 6 - Nov 7
Total with taxes and fees
Americana Condos 10th street
A living room with a sofa, a lamp, a TV, and a view of the sea through a balcony.

12. 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.
$301 nightly
The price is $337
Nov 9 - Nov 10
Total with taxes and fees
Beach Paradise IV-Downtown Waterfront, Top Floor, Luxury Penthouse Condo
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
3.0 star property
Ocean Pines
$805 nightly
The price is $902
Nov 8 - Nov 9
Total with taxes and fees
Game Room! Waterfront Group Haven in Ocean Pines
A house surrounded by dense trees and a wooden dock extending into a body of water.

14. 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.
$370 nightly
The price is $414
Nov 1 - Nov 2
Total with taxes and fees
Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!
A living room with a patterned rug, a bookshelf, a red sofa, and a fish-shaped wall decoration.

15. 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.
$217 nightly
The price is $227
Oct 30 - Oct 31
Total with taxes and fees
Spacious Riverfront Loft Close to Downtown and Dining
A modern kitchen with grey cabinetry, a central island, and pendant lighting.

16. 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.
$830 nightly
The price is $930
Nov 8 - Nov 9
Total with taxes and fees
Game Room! Waterfront Group Haven in Ocean Pines
A covered patio with a table and chairs, a sliding glass door, and a white fence.

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
$219 nightly
The price is $245
Oct 26 - Oct 27
Total with taxes and fees
Monte Carlo Condos
A room with a bed, a chair, a table, and a potted plant.

18. 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.
$355 nightly
The price is $398
Nov 3 - Nov 4
Total with taxes and fees
Ocean Pines Retreat with Beach Club
A spacious living room with a large sofa, a coffee table, and a television. There are large windows with blinds, a ceiling fan, and a door with curtains.

19. Coastal Charm Oasis!

Coastal Charm Oasis!
Ocean Pines
9.8 out of 10, Exceptional, (7 reviews)
"Nice location."
United States
Bill W.
$1,024 nightly
The price is $1,073
Oct 21 - Oct 22
Total with taxes and fees
Coastal Charm Oasis!
A dining area with a wooden table and white chairs, a sofa, and a television in the background.

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.
$298 nightly
The price is $303
Oct 21 - Oct 22
Total with taxes and fees
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pittsville Hotel Reviews

Fenwick Inn

Fenwick Inn

10/10 Excellent
"It was great! Clean room. Staff was great!"
Jeanne 2-night trip
Posted 4 hours ago
Fenwick Inn

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 $73 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.