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Compare 7 Villas in Upperville with updated reviews, rates, and availability.

Private10000sf Retreat GuitarPool Hottub-Wine Area
Private10000sf Retreat GuitarPool Hottub-Wine Area
10.0 out of 10, Exceptional, (22)

Stunning Former Winery w/ Pool & Mtn Views!
Stunning Former Winery w/ Pool & Mtn Views!
9.4 out of 10, Exceptional, (9)

Historic Virginia Wine Country Villa w/ Pool, Yard
Historic Virginia Wine Country Villa w/ Pool, Yard
7.6 out of 10, Good, (15)

Elegant Paris Manor w/ Private Pool!
Elegant Paris Manor w/ Private Pool!
10.0 out of 10, Exceptional, (1)

Elegant Paris Manor w/ Private Pool!
Elegant Paris Manor w/ Private Pool!

Stunning Former Winery w/ Pool & Mtn Views!
Stunning Former Winery w/ Pool & Mtn Views!

Historic Virginia Wine Country Villa w/ Pool, Yard
Historic Virginia Wine Country Villa w/ Pool, Yard
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

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, (84)

Cozy Mountain Cabin w/ Steam Shower! Great for Couples.
Cozy Mountain Cabin w/ Steam Shower! Great for Couples.
10.0 out of 10, Exceptional, (61)
The price is AED 624
AED 1,325 total
includes taxes & fees
21 Apr - 22 Apr

18th Century Stone Cottage minutes from historic Middleburg
18th Century Stone Cottage minutes from historic Middleburg
10.0 out of 10, Exceptional, (38)
The price is AED 1,010
AED 1,466 total
includes taxes & fees
17 Apr - 18 Apr
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

The George Washington Hotel, A Wyndham Grand Hotel
5/5 Excellent
Fabulous
"Historical hotel in heart of Winchester, steps from Old Town. Really felt luxurious ~ credit to all involved. Keep up the good work."
A verified traveler stayed at The George Washington Hotel, A Wyndham Grand Hotel
Posted 11 hours ago
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