Photo by Michael Gibson

Search Hotels with Pool in Upperville

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 availability on Upperville Hotels with Pool

Next weekend
In two weeks

Our top choices for Upperville hotels with a pool

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (2239)
"The place was clean, super friendly front desk staff, SO pet friendly with such a reasonable pet fee, and overall reasonable rate. Would 100% stay here again if I came back through this town. "
United States
Jordyn
The price is Rp1.654.406
Rp1.799.994 total
includes taxes & fees
30 Dec - 31 Dec
La Quinta Inn & Suites by Wyndham Winchester

SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (788)
"Great staff, very clean room with a good breakfast "
United States
Jim
The price is Rp1.793.390
Rp1.951.207 total
includes taxes & fees
4 Jan - 5 Jan 2026
SpringHill Suites by Marriott Winchester

TRU By Hilton Winchester

TRU By Hilton Winchester
2.5 star property
Winchester
9.0 out of 10, Wonderful, (775)
"Clean rooms, courteous staff"
United States
Holly
The price is Rp1.222.050
Rp1.329.590 total
includes taxes & fees
26 Jan - 27 Jan 2026
TRU By Hilton Winchester

DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows
4.0 star property
Front Royal
9.0 out of 10, Wonderful, (1000)
"Friendly staff, nice clean room, hotel restaurant was delicious. "
United States
Dorothy
The price is Rp1.633.977
Rp1.802.277 total
includes taxes & fees
4 Jan - 5 Jan 2026
DoubleTree by Hilton Front Royal Blue Ridge Shadows

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
3.0 star property
Winchester
9.0 out of 10, Wonderful, (1001)
"Great room cozy bed fabulous restaurant great staff on property"
United States
joyce
The price is Rp1.306.110
Rp1.471.216 total
includes taxes & fees
18 Jan - 19 Jan 2026
Holiday Inn Winchester Se-Historic Gateway by IHG

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA
3.0 star property
Winchester
8.8 out of 10, Excellent, (1002)
"Have stayed here multiple times -always good"
United States
Robert
The price is Rp1.377.779
Rp1.499.023 total
includes taxes & fees
25 Jan - 26 Jan 2026
Country Inn & Suites by Radisson, Winchester, VA

Hampton Inn by Hilton Gainesville-Haymarket

Hampton Inn by Hilton Gainesville-Haymarket
2.5 star property
Gainesville
8.8 out of 10, Excellent, (994)
"Friendly staff, clean room, good breakfast "
United States
Vivian
The price is Rp1.663.281
Rp1.896.141 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn by Hilton Gainesville-Haymarket

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
2.5 star property
Winchester
9.0 out of 10, Wonderful, (802)
"We stay here a lot and it is always consistently clean and service is great. "
United States
Kim
The price is Rp1.551.424
Rp1.687.949 total
includes taxes & fees
30 Dec - 31 Dec
Fairfield Inn & Suites by Marriott Winchester

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel
3.5 star property
Old Town Winchester
9.4 out of 10, Exceptional, (1010)
"Great hotel!"
United States
CHARLES
The price is Rp2.120.754
Rp2.402.815 total
includes taxes & fees
4 Jan - 5 Jan 2026
The George Washington Hotel, A Wyndham Grand Hotel

Homewood Suites by Hilton Leesburg

Homewood Suites by Hilton Leesburg
3.0 star property
Leesburg
9.2 out of 10, Wonderful, (543)
"Very clean roomy and sufficient parking close to evrrything "
United States
Noel
The price is Rp1.663.281
Rp1.912.771 total
includes taxes & fees
11 Jan - 12 Jan 2026
Homewood Suites by Hilton Leesburg
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.

Top Upperville Hotel Reviews

Frequently asked questions

What are some accommodation options with pools in Upperville?
Hilton Garden Inn Dulles North: Features complimentary high-speed (wired) Internet access, an indoor pool and free self parking. Lansdowne Resort and Spa: Offers a seasonal outdoor pool, an indoor pool and 3 outdoor tennis courts. Salamander Resort And Spa: Provides a children's pool, a seasonal outdoor pool and 2 restaurants. Microtel Inn & Suites by Wyndham Winchester: Features daily, an indoor pool and free self parking. La Quinta Inn & Suites by Wyndham Winchester: Offers buffet, an indoor pool and complimentary high-speed (wired) Internet access.
What is there to see and do in Upperville?
Surround yourself with nature at Upperville Park. Discover sights such as Sky Meadows State Park during your stay.
When is the best time to book a hotel with a pool in Upperville?
You may want to think about a place to stay that has an outdoor pool if you're planning to visit Upperville in the hottest months of July, August or June, when the average temperature is 22°C. Accommodation offering an indoor pool may be the way to go if you come to town during the coldest months of January, February or December, when the average temperature is 3°C.