Pittsville Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Vacation Rentals in Pittsville

Aparthotel in Midtown Ocean City

3.0 star property
7.4 out of 10, Good, (1297)
"Scenic area with wonderful wooden bridges and view of water. There was no hot water to shower, but not a deal breaker."
United States
Isolda
The price is ¥11,881
¥15,053 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Coconut Malorie Resort Ocean City, Ascend Collection Hotel

Aparthotel in Downtown Ocean City

2.5 star property
6.2 out of 10, (350)
"Clean and very friendly staff"
United States
Randy
Majestic Hotel & Apartments

Apartment in North Ocean City

3.0 star property
9.2 out of 10, Wonderful, (133)
"Our room was very clean and the ocean view was breathtaking. "
United States
Kelly
Saint Tropez

Cottage in Berlin

3.0 star property
9.4 out of 10, Exceptional, (300)
"Was a great place to bring kids and dogs! "
United States
AMANDA
Shore Point Cottages

Apartment in North Ocean City

3.5 star property
8.6 out of 10, Excellent, (58)
"Property was in a great location. Check in and check out was easy. Having a hot tub and deck with table and chairs was nice. Unit was clean with an exception of the floors. I can understand it being a little sandy because of being at the beach, but there were tortilla chips in several areas of the floor. "
United States
Tami
Club Ocean Villas II by Coolvacay

Condo in Downtown Ocean City

3.5 star property
8.4 out of 10, Very Good, (19)
"straight fire, definitely going back"
United States
stephen
The price is ¥25,434
¥71,336 total
includes taxes & fees
Dec 13 - Dec 14
Americana Condos 10th street

Condo resort in Midtown Ocean City

3.0 star property
8.4 out of 10, Very Good, (39)
"One of the cleanest places I’ve stay at loved it ! "
United States
Kelsey
Bay Club Resort by Coolvacay

Condo in Downtown Ocean City

9.8 out of 10, Exceptional, (62)
"The condo was very convenient to get to the beach. Beautiful view of the bay. Plenty of room for everyone to enjoy the stay. "
United States
David H.
The price is ¥7,611
¥54,828 total
includes taxes & fees
Dec 14 - Dec 15
Beach Paradise IV-Downtown Waterfront, Top Floor, Luxury Penthouse Condo

Vacation Home in North Ocean City

9.8 out of 10, Exceptional, (134)
"Very lovely pkace!! Would def book again!!"
United States
Brenda F.
The price is ¥7,611
¥47,759 total
includes taxes & fees
Dec 8 - Dec 9
BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!

Aparthotel in Downtown Ocean City

3.0 star property
7.4 out of 10, Good, (170)
"Close to boardwalk, beach, shopping and dining. Also it was very affordable."
United States
ANGELA
Boardwalk One

Vacation Home in North Ocean City

9.8 out of 10, Exceptional, (119)
"Great property in a great location. Host was quick to get ahold of and the instructions were incredibly easy. Highly recommend this property for a family or large group. We would stay here again!"
United States
Joseph G.
The price is ¥6,850
¥46,916 total
includes taxes & fees
Dec 8 - Dec 9
"BEACH PARADISE II" 4-BR/3.5-BA Exquisite Townhouse with POOL & GARAGE

Condo in Downtown Ocean City

3.0 star property
6.8 out of 10, (58)
"The condo was small, but it’s still accommodated my family of eight and we were right next to the pool, which was great for the kids anytime we needed something. We just called the Hotel and it was brought over in a reasonable amount of time or we could pick it up later. Staff were very friendly."
United States
Amy
Monte Carlo Condos

Vacation Home in North Ocean City

9.8 out of 10, Exceptional, (142)
"We had great time. The house was clean and perfect for my entire family. I would recommend and go back. "
United States
Kristina P.
DownByTheBay-115 WATERFRONT! 4 BR/3.5BA at Broad Marsh OC with GARAGE Sleeps 15

Apartment in Downtown Ocean City

3.0 star property
9.2 out of 10, Wonderful, (5)
"Everything around was excelente, only bad things wasn’t clean and need some updates, everything else was really nice. The hostess was friendly and helpful. "
United States
Anonymous traveler
ELIS APARTMENT

Vacation Home in North Ocean City

9.8 out of 10, Exceptional, (11)
"Beautiful home. Our family of 13 were very comfortable and really enjoyed our stay. Only negative was no furniture on the deck. The pictures showed a table and chairs along with couches and comfy chairs. We had to bring out beach chairs to sit. Loved the big side yard and fire pit. "
United States
Peggy K.
⭐️Brand New High End Luxury Bayside Mansion Pool⭐️

Condo in Downtown Ocean City

9.6 out of 10, Exceptional, (49)
"Overall a very nice property. Great location with many food and activity options within walking distance."
United States
Erik G.
The price is ¥13,824
¥60,001 total
includes taxes & fees
Dec 8 - Dec 9
SunburstParadise: LUX TH OceanView DOWNTOWN BOARDWALK 3BR 3BA with 2 Car Garage

Condo in Midtown Ocean City

9.8 out of 10, Exceptional, (246)
"Will stay again. Perfect for our needs. "
United States
thomasine m.
The price is ¥17,708
¥35,173 total
includes taxes & fees
Dec 8 - Dec 9
Ocean City Maryland Condo, ocean side 50 steps to the beach! On 7 40th Street

Condo in Downtown Ocean City

10.0 out of 10, Exceptional, (102)
"We had an amazing stay at this property. It was well stocked, clean, had comfy beds, and a beautiful view. "
United States
Abby W.
Updated, Direct Bay Front, Bay Front Pool, 3 Blocks to Beach and Boardwalk

Condo in Downtown Ocean City

10.0 out of 10, Exceptional, (12)
"Great weekend stay"
United States
Susan
Summer Special Discounts! // Close To The Boardwalk // 2 Parking Spots!

Condo in Midtown Ocean City

9.8 out of 10, Exceptional, (138)
"Great place and location."
United States
John P.
Beautiful Midtown Ocean View/Block 36th St
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Pittsville Hotel Reviews

Find out more about Pittsville

Search for holiday rentals in Pittsville on Expedia! You can easily find your home rentals, villas, holiday apartments in Pittsville using one of the methods below:

  • View our selection of featured holiday rentals in Pittsville
  • Use the map to find apartments and other holiday homes in the Pittsville neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Pittsville while they last

Look no further and take a look at our great range of rental properties in Pittsville!

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?

BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!: This vacation home rental near Pittsville is located next to a golf course and has an outdoor pool, a balcony, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

What can I see and do in Pittsville?

While exploring the area, visit family-friendly sights like Salisbury Zoo, or get outside and enjoy nature at Assawoman Bay. Centre at Salisbury and Wicomico Youth and Civic Center 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.