Search Hotels with Pool in Pittsville

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
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Pittsville Hotels with Pool

Tonight
29 Dec - 30 Dec
Tomorrow
30 Dec - 31 Dec
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Pittsville hotels with a pool

Indoor pool, outdoor pool
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront
3.0 star property
Downtown Ocean City
9.0 out of 10, Wonderful, (3377)
"Yes, I great place y to o stay"
United States
James
Grand Hotel Ocean City Oceanfront
Balcony view
Park Place Hotel

Park Place Hotel

Park Place Hotel
3.0 star property
Downtown Ocean City
9.2 out of 10, Wonderful, (1064)
"Great location, friendly staff."
United States
Yun-Ping
Park Place Hotel
Outdoor pool
Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton
3.5 star property
Fenwick Island
9.4 out of 10, Exceptional, (699)
"Another great stay!"
United States
Robert
The price is ฿2,519
฿2,809 total
includes taxes & fees
1 Jan - 2 Jan 2026
Fenwick Shores, Tapestry Collection by Hilton
Indoor pool, seasonal outdoor pool
Hampton Inn & Suites Ocean City/Bayfront-Convention Center

Hampton Inn & Suites Ocean City/Bayfront-Convention Center

Hampton Inn & Suites Ocean City/Bayfront-Convention Center
2.5 star property
Midtown Ocean City
8.8 out of 10, Excellent, (1007)
"Very clean comfortable stay"
United States
Keiyanna
The price is ฿1,820
฿2,039 total
includes taxes & fees
11 Jan - 12 Jan 2026
Hampton Inn & Suites Ocean City/Bayfront-Convention Center
Indoor pool, 2 outdoor pools, pool umbrellas, pool loungers
DoubleTree by Hilton Ocean City Oceanfront

DoubleTree by Hilton Ocean City Oceanfront

DoubleTree by Hilton Ocean City Oceanfront
4.0 star property
Midtown Ocean City
9.0 out of 10, Wonderful, (1004)
"Staff was nice "
United States
Mersed
The price is ฿2,585
฿2,895 total
includes taxes & fees
5 Jan - 6 Jan 2026
DoubleTree by Hilton Ocean City Oceanfront
Property amenity
Fenwick Inn

Fenwick Inn

Fenwick Inn
3.0 star property
North Ocean City
8.8 out of 10, Excellent, (2005)
"Clean, nice staff and convenient location. "
United States
Jessica
Fenwick Inn
Indoor pool, seasonal outdoor pool, pool umbrellas, pool loungers
Hyatt Place Ocean City / Oceanfront

Hyatt Place Ocean City / Oceanfront

Hyatt Place Ocean City / Oceanfront
3.0 star property
Downtown Ocean City
9.0 out of 10, Wonderful, (1589)
"Great place"
United States
Andrew
The price is ฿2,461
฿2,756 total
includes taxes & fees
6 Jan - 7 Jan 2026
Hyatt Place Ocean City / Oceanfront
Indoor pool, open 6:00 AM to 10:00 PM, pool loungers
Hilton Garden Inn Ocean City Oceanfront

Hilton Garden Inn Ocean City Oceanfront

Hilton Garden Inn Ocean City Oceanfront
3.0 star property
Midtown Ocean City
9.0 out of 10, Wonderful, (1116)
"The room was extra clean and neat made for a great stay"
United States
Rex
The price is ฿2,266
฿2,537 total
includes taxes & fees
11 Jan - 12 Jan 2026
Hilton Garden Inn Ocean City Oceanfront
Exterior
Holiday Inn Ocean City by IHG

Holiday Inn Ocean City by IHG

Holiday Inn Ocean City by IHG
3.0 star property
North Ocean City
8.4 out of 10, Very good, (1003)
"Clean room, great view, friendly staff!"
United States
Amanda
The price is ฿2,017
฿2,259 total
includes taxes & fees
12 Jan - 13 Jan 2026
Holiday Inn Ocean City by IHG
Indoor pool
Tru by Hilton Ocean City Bayside

Tru by Hilton Ocean City Bayside

Tru by Hilton Ocean City Bayside
2.5 star property
Midtown Ocean City
9.0 out of 10, Wonderful, (1002)
"Clean rooms, safe parking and very friendly staff"
United States
Criss
The price is ฿2,138
฿2,394 total
includes taxes & fees
5 Jan - 6 Jan 2026
Tru by Hilton Ocean City Bayside
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

Top Pittsville Hotel Reviews

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

10/10 Excellent
"The Grand is always a great place to stay in the summer or the winter!"
maureen 3-night trip
Posted 2 days ago
Grand Hotel Ocean City Oceanfront

Frequently asked questions

What are some hotels with pools in Pittsville?
Grand Hotel Ocean City Oceanfront: Hotel, 1-minute walk from Ocean City Boardwalk. Features an indoor pool, an outdoor pool and 4 restaurants. Hyatt Place Ocean City / Oceanfront: Hotel, 1-minute walk from Ocean City Boardwalk. Offers a seasonal outdoor pool, an indoor pool and a snack bar/deli. Hilton Garden Inn Ocean City Oceanfront: Hotel, 2-minute walk from Ocean City Boardwalk. Provides a snack bar/deli, a pool and free self parking. Howard Johnson Plaza Hotel by Wyndham Ocean City Oceanfront: Hotel, 1-minute walk from Ocean City Boardwalk. Features free self parking, a pool and complimentary wireless Internet access. Carousel Resort Hotel & Condominiums: Hotel, 2-minute walk from Ocean City Beach. Offers a children's pool, a seasonal outdoor pool and a sauna.
What is there to see and do in Pittsville?
Make a point to visit attractions such as Salisbury Zoo and Frontier Town Water Park and Golf. During your stay, visit sights such as Centre at Salisbury, Wicomico Youth and Civic Center and Henry S. Parker Athletic Complex.
When is the best time to book a hotel with a pool in Pittsville?
You may want to consider accommodation with an outdoor swimming pool if you're planning to visit Pittsville in the hottest months of July, August or June, when the average temp is 24°C. Accommodation with an indoor pool may be what you want if you are visiting during the coldest months of January, February or December, when the average temperature is 5°C.