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Our top choices for Upperville hotels with a pool

9.4 out of 10, Exceptional, (788)
The price is ฿3,333
฿3,627 total
includes taxes & fees
4 Jan - 5 Jan 2026

DoubleTree by Hilton Front Royal Blue Ridge Shadows
DoubleTree by Hilton Front Royal Blue Ridge ShadowsFront Royal
9.0 out of 10, Wonderful, (1006)
The price is ฿3,037
฿3,350 total
includes taxes & fees
29 Dec - 30 Dec

8.8 out of 10, Excellent, (1004)
The price is ฿5,293
฿7,188 total
includes taxes & fees
1 Jan - 2 Jan 2026

8.8 out of 10, Excellent, (993)
The price is ฿3,048
฿3,475 total
includes taxes & fees
30 Dec - 31 Dec

9.2 out of 10, Wonderful, (2239)
The price is ฿3,075
฿3,346 total
includes taxes & fees
28 Dec - 29 Dec

Holiday Inn Express & Suites Leesburg - Historic District by IHG
Holiday Inn Express & Suites Leesburg - Historic District by IHGLeesburg
9.0 out of 10, Wonderful, (1003)
The price is ฿3,268
฿3,758 total
includes taxes & fees
11 Jan - 12 Jan 2026

9.2 out of 10, Wonderful, (541)
The price is ฿3,092
฿3,555 total
includes taxes & fees
11 Jan - 12 Jan 2026

Holiday Inn Winchester Se-Historic Gateway by IHG
Holiday Inn Winchester Se-Historic Gateway by IHGWinchester
9.0 out of 10, Wonderful, (1005)
The price is ฿2,552
฿2,870 total
includes taxes & fees
26 Dec - 27 Dec
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.
Top Upperville Hotel Reviews

Lansdowne Resort and Spa
10/10 Excellent


































