A sign for the Village of UPPERVILLE with a 'Please drive slowly' message.

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Check availability on Upperville Hotels with Swimming Pool

This weekend
6 Nov - 8 Nov
Next weekend
13 Nov - 15 Nov

Choose what matters most at hotels with a pool in Upperville

Breakfast included
4 stars

Top Upperville Hotel Reviews

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

8/10 Good
"Clean room, good staff, good location"
Gregory 2-night trip
Posted 1 day ago
Travelodge by Wyndham Winchester

Frequently asked questions

What are some accommodation options with pools in Upperville?
The George Washington Hotel, A Wyndham Grand Hotel: Features 2 restaurants, an indoor pool and a full-service spa. Salamander Resort And Spa: Offers a children's pool, a seasonal outdoor pool and 2 restaurants. Lansdowne Resort and Spa: Provides a seasonal outdoor pool, an indoor pool and 3 outdoor tennis courts. Travelodge by Wyndham Winchester: Offers a health club, an indoor pool and daily. TRU By Hilton Winchester: Features 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.