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Search Hotels with Pool in Upperville

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Check availability on Upperville Hotels with Pool

Tonight
23 Dec - 24 Dec
Tomorrow
24 Dec - 25 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Upperville hotels with a pool

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, (788)
"Great staff, very clean room with a good breakfast "
United States
Jim
The price is ฿3,333
฿3,627 total
includes taxes & fees
4 Jan - 5 Jan 2026
SpringHill Suites by Marriott Winchester
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, (1006)
"Friendly staff, nice clean room, hotel restaurant was delicious. "
United States
Dorothy
The price is ฿3,037
฿3,350 total
includes taxes & fees
29 Dec - 30 Dec
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Indoor pool, seasonal outdoor pool
Lansdowne Resort and Spa

Lansdowne Resort and Spa

Lansdowne Resort and Spa
4.0 star property
Leesburg
8.8 out of 10, Excellent, (1004)
"Great place"
United States
Joyce
The price is ฿5,293
฿7,188 total
includes taxes & fees
1 Jan - 2 Jan 2026
Lansdowne Resort and Spa
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, (993)
"Friendly staff, clean room, good breakfast "
United States
Vivian
The price is ฿3,048
฿3,475 total
includes taxes & fees
30 Dec - 31 Dec
Hampton Inn by Hilton Gainesville-Haymarket
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, (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. "
United States
Jordyn
The price is ฿3,075
฿3,346 total
includes taxes & fees
28 Dec - 29 Dec
La Quinta Inn & Suites by Wyndham Winchester
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, (1003)
"Great stay! The king suite was spacious and clean! Would definitely stay at this location again. "
United States
Kaitlin
The price is ฿3,268
฿3,758 total
includes taxes & fees
11 Jan - 12 Jan 2026
Holiday Inn Express & Suites Leesburg - Historic District by IHG
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, (541)
"Very clean roomy and sufficient parking close to evrrything "
United States
Noel
The price is ฿3,092
฿3,555 total
includes taxes & fees
11 Jan - 12 Jan 2026
Homewood 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, (1005)
"Great room cozy bed fabulous restaurant great staff on property"
United States
joyce
The price is ฿2,552
฿2,870 total
includes taxes & fees
26 Dec - 27 Dec
Holiday Inn Winchester Se-Historic Gateway by IHG
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, (772)
"Very nice room and common spaces. Breakfast was good and the price was very fair."
United States
Joseph
The price is ฿2,271
฿2,471 total
includes taxes & fees
5 Jan - 6 Jan 2026
TRU By Hilton Winchester
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, (213)
"Clean room, great staff, great food, nice pool!"
United States
Jeff
The price is ฿3,797
฿4,367 total
includes taxes & fees
4 Jan - 5 Jan 2026
Home2 Suites by Hilton Leesburg
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

Lansdowne Resort and Spa

Lansdowne Resort and Spa

10/10 Excellent
"We’ve stayed there multiple times over the years and it seems better than ever. So well kept. We live locally so "
David 1-night trip
Posted 10 days ago
Lansdowne Resort and Spa

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. 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 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.