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Find Hotels with a Pool in Upperville, VA

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Check availability on Upperville Hotels with a Pool

Our top choices for Upperville hotels with a pool

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, (2226)
"Rooms are always clean when I stay and the staff was very friendly. "
United States
Ashley
The price is ₩145,856
₩158,691 total
includes taxes & fees
Dec 21 - Dec 22
La Quinta Inn & Suites by Wyndham Winchester
Property amenity
SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (783)
"Great staff, very clean room with a good breakfast "
United States
Jim
The price is ₩149,325
₩162,467 total
includes taxes & fees
Jan 4 - Jan 5, 2026
SpringHill Suites by Marriott Winchester
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, (770)
"Very nice room and common spaces. Breakfast was good and the price was very fair."
United States
Joseph
The price is ₩107,739
₩117,220 total
includes taxes & fees
Jan 7 - Jan 8, 2026
TRU By Hilton Winchester
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, (1000)
"Have stayed here multiple times -always good"
United States
Robert
The price is ₩121,941
₩132,672 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Country Inn & Suites by Radisson, Winchester, VA
Terrace/patio
Homewood Suites by Hilton Leesburg

Homewood Suites by Hilton Leesburg

Homewood Suites by Hilton Leesburg
3.0 star property
Leesburg
9.2 out of 10, Wonderful, (540)
"Very clean roomy and sufficient parking close to evrrything "
United States
Noel
The price is ₩146,639
₩168,634 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Homewood Suites by Hilton Leesburg
Indoor pool, outdoor pool
Holiday Inn Express & Suites Leesburg - Historic District by IHG

Holiday Inn Express & Suites Leesburg - Historic District by IHG

Holiday Inn Express & Suites Leesburg - Historic District by IHG
2.5 star property
Leesburg
9.0 out of 10, Wonderful, (1002)
"Great stay! The king suite was spacious and clean! Would definitely stay at this location again. "
United States
Kaitlin
The price is ₩155,009
₩178,262 total
includes taxes & fees
Dec 21 - Dec 22
Holiday Inn Express & Suites Leesburg - Historic District by IHG
Indoor pool
Hampton Inn by Hilton Gainesville-Haymarket

Hampton Inn by Hilton Gainesville-Haymarket

Hampton Inn by Hilton Gainesville-Haymarket
2.5 star property
Gainesville
8.8 out of 10, Excellent, (992)
"Friendly staff, clean room, good breakfast "
United States
Vivian
The price is ₩142,092
₩161,985 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Hampton Inn by Hilton Gainesville-Haymarket
Indoor pool
Home2 Suites by Hilton Leesburg

Home2 Suites by Hilton Leesburg

Home2 Suites by Hilton Leesburg
3.0 star property
Leesburg
9.8 out of 10, Exceptional, (212)
"Clean room, great staff, great food, nice pool!"
United States
Jeff
The price is ₩180,106
₩207,122 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Home2 Suites by Hilton Leesburg
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, (1000)
"Great room cozy bed fabulous restaurant great staff on property"
United States
joyce
The price is ₩121,055
₩136,137 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
Indoor pool
DoubleTree by Hilton Front Royal Blue Ridge Shadows

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 ₩144,055
₩158,894 total
includes taxes & fees
Dec 25 - Dec 26
DoubleTree by Hilton Front Royal Blue Ridge Shadows
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

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"Yes"
Mark 1-night trip
Posted 4 days ago
La Quinta Inn & Suites by Wyndham Winchester

Frequently asked questions

What are some accommodations with pools in Upperville?
Hilton Garden Inn Dulles North: Features complimentary 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 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 with an outdoor swimming pool if you will be visiting Upperville in the hottest months of July, August, or June when the average temperature is 72°F. Lodging offering an indoor pool may be the way to go if you are visiting during the coldest months of January, February, or December when the average temperature is 37°F.