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Compare 254 Vacation Homes in Upperville with updated reviews, rates, and availability.

Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains
Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains
9.8 out of 10, Exceptional, (28)

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
9.6 out of 10, Exceptional, (91)

Modern Country House on the Shenandoah River
Modern Country House on the Shenandoah River
9.8 out of 10, Exceptional, (31)

5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine
5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine
9.8 out of 10, Exceptional, (47)

Cottage on King | Charming Historic Leesburg Home
Cottage on King | Charming Historic Leesburg Home
9.4 out of 10, Exceptional, (49)
The price is SAR 473
SAR 988 total
includes taxes & fees
2 Apr - 3 Apr

Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
9.8 out of 10, Exceptional, (93)

The Lodge at Bear Rock
The Lodge at Bear Rock

Charles Town Home w/ Private Pool & Hot Tub
Charles Town Home w/ Private Pool & Hot Tub
10.0 out of 10, Exceptional, (41)
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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Other property types in Upperville

Cozy Mountain Cabin w/ Steam Shower! Great for Couples.
Cozy Mountain Cabin w/ Steam Shower! Great for Couples.
10.0 out of 10, Exceptional, (59)
The price is SAR 600
SAR 1,307 total
includes taxes & fees
2 Apr - 3 Apr

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
10.0 out of 10, Exceptional, (83)

Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>
Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>
10.0 out of 10, Exceptional, (37)
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.
Recent reviews of Upperville hotels
Recent reviews of Upperville hotels

Spark by Hilton Winchester
5/5 Excellent
"Good hôtel, thought it was full breakfast "
A verified traveler stayed at Spark by Hilton Winchester
Posted 3 hours ago
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