Photo by Michael Gibson
Search Hotels with Pool in Upperville
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check availability on Upperville Hotels with Pool
Our top choices for Upperville hotels with a pool
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. "
Jordyn
The price is Rp1.654.406
Rp1.799.994 total
includes taxes & fees
30 Dec - 31 Dec
9.4 out of 10, Exceptional, (788)
"Great staff, very clean room with a good breakfast "
Jim
The price is Rp1.793.390
Rp1.951.207 total
includes taxes & fees
4 Jan - 5 Jan 2026
9.0 out of 10, Wonderful, (775)
"Clean rooms, courteous staff"
Holly
The price is Rp1.222.050
Rp1.329.590 total
includes taxes & fees
26 Jan - 27 Jan 2026
DoubleTree by Hilton Front Royal Blue Ridge Shadows
DoubleTree by Hilton Front Royal Blue Ridge ShadowsFront Royal
9.0 out of 10, Wonderful, (1000)
"Friendly staff, nice clean room, hotel restaurant was delicious. "
Dorothy
The price is Rp1.633.977
Rp1.802.277 total
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
Holiday Inn Winchester Se-Historic Gateway by IHGWinchester
9.0 out of 10, Wonderful, (1001)
"Great room cozy bed fabulous restaurant great staff on property"
joyce
The price is Rp1.306.110
Rp1.471.216 total
includes taxes & fees
18 Jan - 19 Jan 2026
Country Inn & Suites by Radisson, Winchester, VA
Country Inn & Suites by Radisson, Winchester, VAWinchester
8.8 out of 10, Excellent, (1002)
"Have stayed here multiple times -always good"
Robert
The price is Rp1.377.779
Rp1.499.023 total
includes taxes & fees
25 Jan - 26 Jan 2026
8.8 out of 10, Excellent, (994)
"Friendly staff, clean room, good breakfast "
Vivian
The price is Rp1.663.281
Rp1.896.141 total
includes taxes & fees
4 Jan - 5 Jan 2026
Fairfield Inn & Suites by Marriott Winchester
Fairfield Inn & Suites by Marriott WinchesterWinchester
9.0 out of 10, Wonderful, (802)
"We stay here a lot and it is always consistently clean and service is great. "
Kim
The price is Rp1.551.424
Rp1.687.949 total
includes taxes & fees
30 Dec - 31 Dec
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
Quality Inn Winchester
10/10 Excellent
Salamander Resort And Spa
10/10 Excellent