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Search Hotels with Swimming Pool in Upperville

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Check availability on Upperville Hotels with Swimming Pool

Our top choices for Upperville hotels with a pool

Indoor pool
TRU By Hilton Winchester

TRU By Hilton Winchester

TRU By Hilton Winchester
2.5 star property
Winchester
9.0 out of 10, Wonderful, (765)
"The hotel was clean and the staff was pleasant."
United States
Sherri
The price is ₹6,558
₹7,135 total
includes taxes & fees
7 Jan - 8 Jan 2026
TRU By Hilton Winchester
Indoor pool
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1375)
"Excellent accommodations"
United States
Loretta
The price is ₹6,558
₹7,135 total
includes taxes & fees
7 Jan - 8 Jan 2026
Microtel Inn & Suites by Wyndham Winchester
Indoor pool
Clarion Inn Harpers Ferry - Charles Town

Clarion Inn Harpers Ferry - Charles Town

Clarion Inn Harpers Ferry - Charles Town
2.5 star property
Harpers Ferry
7.8 out of 10, Good, (1001)
"Very nice people in the front desk"
United States
Ximena
The price is ₹8,022
₹8,985 total
includes taxes & fees
22 Dec - 23 Dec
Clarion Inn Harpers Ferry - Charles Town
Indoor pool
Country Inn & Suites by Radisson, Winchester, VA

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, (1001)
"Have stayed here multiple times -always good"
United States
Robert
The price is ₹7,658
₹8,332 total
includes taxes & fees
4 Jan - 5 Jan 2026
Country Inn & Suites by Radisson, Winchester, VA
Indoor pool
La Quinta Inn & Suites by Wyndham Winchester

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, (2221)
"Rooms are always clean when I stay and the staff was very friendly. "
United States
Ashley
The price is ₹9,307
₹10,127 total
includes taxes & fees
5 Jan - 6 Jan 2026
La Quinta Inn & Suites by Wyndham Winchester
Seasonal outdoor pool
Quality Inn Winchester

Quality Inn Winchester

Quality Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1001)
"Great stay"
United States
Jaron
The price is ₹6,800
₹7,398 total
includes taxes & fees
17 Dec - 18 Dec
Quality Inn Winchester
Indoor pool
Hampton Inn & Suites Charles Town

Hampton Inn & Suites Charles Town

Hampton Inn & Suites Charles Town
2.5 star property
Charles Town
9.4 out of 10, Exceptional, (1001)
"Great stay for a quick day trip to visit family. "
United States
Barbara
The price is ₹9,060
₹10,148 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn & Suites Charles Town
Indoor pool
Holiday Inn Winchester Se-Historic Gateway by IHG

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)
"Todo excelente "
Mexico
Anner Javier
The price is ₹6,651
₹7,506 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Winchester Se-Historic Gateway by IHG
Seasonal outdoor pool, open 9 AM to 10 PM, pool loungers
Holiday Inn Express Winchester South-Stephens City by IHG

Holiday Inn Express Winchester South-Stephens City by IHG

Holiday Inn Express Winchester South-Stephens City by IHG
2.5 star property
Stephens City
8.2 out of 10, Very good, (802)
"Nice stay and friendly people "
United States
ALFRED
The price is ₹6,651
₹7,237 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express Winchester South-Stephens City by IHG
Indoor pool
The George Washington Hotel, A Wyndham Grand Hotel

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, (1007)
"Great hotel!"
United States
CHARLES
The price is ₹11,384
₹12,898 total
includes taxes & fees
17 Dec - 18 Dec
The George Washington Hotel, A Wyndham Grand Hotel
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.
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Top Upperville Hotel Reviews

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

10/10 Excellent
"Staff is fantastic and breakfast is always great. "
LESLIE 3-night trip
Posted 5 days ago
Holiday Inn Winchester Se-Historic Gateway by IHG

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Frequently asked questions

What are some accommodation options with pools in Upperville?
Lansdowne Resort and Spa: Features a seasonal outdoor pool, an indoor pool and 3 outdoor tennis courts. Hilton Garden Inn Dulles North: Offers complimentary high-speed (wired) Internet access, an indoor pool and free self parking. Salamander Resort And Spa: Provides a children's pool, a seasonal outdoor pool and 2 restaurants. La Quinta Inn & Suites by Wyndham Winchester: Features buffet, an indoor pool and complimentary high-speed (wired) Internet access. Microtel Inn & Suites by Wyndham Winchester: Offers daily, an indoor pool and free self parking.
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.