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Hotels with Pool & Resorts in Upperville from AU$118

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Check availability on Upperville Hotels with Pool

Tonight
6 Dec - 7 Dec
Tomorrow
7 Dec - 8 Dec
Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec

Best Upperville Hotels with Pool

Indoor pool
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 AU$119
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

2.5 star property
Winchester
9.2 out of 10, Wonderful, (1373)
"Excellent accommodations"
United States
Loretta
The price is AU$118
includes taxes & fees
5 Jan - 6 Jan 2026
Microtel Inn & Suites by Wyndham Winchester
Indoor pool
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 AU$132
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

3.0 star property
Winchester
9.2 out of 10, Wonderful, (2216)
"Rooms are always clean when I stay and the staff was very friendly. "
United States
Ashley
The price is AU$171
includes taxes & fees
16 Dec - 17 Dec
La Quinta Inn & Suites by Wyndham Winchester
Indoor pool
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, (1008)
"Wonderful stay - staff was friendly and knowledgeable about the goings on in town for the holidays which helped plan our trip can’t wait to go back"
United States
Jeanette
The price is AU$216
includes taxes & fees
14 Dec - 15 Dec
The George Washington Hotel, A Wyndham Grand Hotel
Indoor pool
SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester

2.5 star property
Winchester
9.4 out of 10, Exceptional, (773)
"Clean room, courteous and professional staff. Great breakfast selections"
United States
Lauris
The price is AU$175
includes taxes & fees
14 Dec - 15 Dec
SpringHill Suites by Marriott Winchester
Fitness facility
Courtyard by Marriott Winchester

Courtyard by Marriott Winchester

3.0 star property
Winchester
9.0 out of 10, Wonderful, (912)
"comfortable room, amenities and staff"
United States
Prashant
The price is AU$175
includes taxes & fees
13 Dec - 14 Dec
Courtyard by Marriott Winchester
Indoor pool
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 AU$151
includes taxes & fees
14 Dec - 15 Dec
Clarion Inn Harpers Ferry - Charles Town
Indoor pool
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 AU$167
includes taxes & fees
14 Dec - 15 Dec
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Indoor pool
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, (1004)
"Clean room, nicely furnished."
United States
Marilyn
The price is AU$126
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Winchester Se-Historic Gateway by IHG
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

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

10/10 Excellent
"Très très bien déjeuné wow depuis 20 ans que je passe par la ils s'améliore toujours "
roger 1-night trip
Posted 2 days ago
Travelodge by Wyndham Winchester

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. Travelodge by Wyndham Winchester: Provides a children's pool, a seasonal outdoor pool and 2 restaurants. Salamander Resort And Spa: Features buffet, an indoor pool and complimentary high-speed (wired) Internet access. La Quinta Inn & Suites by Wyndham Winchester: Offers daily, an indoor pool and free self parking. Microtel Inn & Suites by Wyndham Winchester: Features buffet, 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.