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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

10.0 out of 10, Exceptional, (31)
"We were there over the Christmas holidays, The farmhouse was very nicely decorated for Christmas, we were very happy with the accommodations and would definitely stay there again"
Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

9.6 out of 10, Exceptional, (91)
"Great family stay! Highly recommend "
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

Modern Country House on the Shenandoah River

9.8 out of 10, Exceptional, (33)
"This was a perfect long weekend stay for two families (4 adults, 4 kids). Comfortable, spacious, and well-equipped house on a beautiful property. Very responsive and helpful host. Would give 6 stars if I could. We hope to be back soon!"
Modern Country House on the Shenandoah River

5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine

9.8 out of 10, Exceptional, (49)
"Wonderful house and grounds for a family wedding."
5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine

Cottage on King | Charming Historic Leesburg Home

9.4 out of 10, Exceptional, (50)
"Walkable to downtown historic Leesburg. Clean and super cute little house. Would stay again! "
The price is SAR 517
SAR 1,159 total
includes taxes & fees
6 May - 7 May
Cottage on King | Charming Historic Leesburg Home

Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

9.8 out of 10, Exceptional, (94)
"What a perfect home for our Thanksgiving celebration! There were so many rooms in which to spread out, the beds were comfortable, and the location was central to necessities. We had a great stay!"
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

The Lodge at Bear Rock

The Lodge at Bear Rock

Charles Town Home w/ Private Pool & Hot Tub

10.0 out of 10, Exceptional, (43)
"Our families decided to rent the property for a getaway close to the DMV. It was easy to check in, get around Charles Town and enjoy the property. Even with an unexpected 6" of snow, we still found time to appreciate everything the property had to offer."
Charles Town Home w/ Private Pool & Hot Tub

Pets? YES! Hot Tub ★ Gym ★ Firepit ★ Game Room ★ Path to Winery

9.8 out of 10, Exceptional, (47)
"Great home for a family trip, very spacious for the family to spread out. "
Pets? YES! Hot Tub ★ Gym ★ Firepit ★ Game Room ★ Path to Winery

Balcony & Pool Access: Modern Gainesville Home

10.0 out of 10, Exceptional, (1)
"The townhouse was great- very clean and plenty of room for my family of six. I do wish there was a bigger bed in the Master bedroom- the mattress was thin and the bed was squeaky to sleep in. Property manager was great- very easy to communicate with very helpful. "
The price is SAR 570
SAR 1,881 total
includes taxes & fees
11 May - 12 May
Balcony & Pool Access: Modern Gainesville Home

Big Sunny Family House

10.0 out of 10, Exceptional, (30)
"Wonderful stay. "
The price is SAR 563
SAR 1,528 total
includes taxes & fees
13 May - 14 May
Big Sunny Family House

Chic Front Royal Retreat Near Shenandoah River!

9.6 out of 10, Exceptional, (16)
"Very great location (to both the quaint downtown of Front Royal to the Shenandoah national park. the house had everything we needed for our 4-night stay (and we did a lot of cooking in the house too). Also, a walk away from the river and trails. Great stay, correspondence, and value!"
Chic Front Royal Retreat Near Shenandoah River!

Indulge in Elegance: 7 BR Manor with Events in Historic Waterford

Indulge in Elegance: 7 BR Manor with Events in Historic Waterford

Historic 180 Acre Estate In The Hunt Country Of Loudoun County, Virginia

10.0 out of 10, Exceptional, (54)
"We stayed for 3 days and loved it. The garden was beautiful and loved seeing the cows!"
Historic 180 Acre Estate In The Hunt Country Of Loudoun County, Virginia

Modern Mountain Retreat w/ Deck + Hot Tub!

10.0 out of 10, Exceptional, (69)
"The owner communicated well and was very responsive. The fireplace stove was great and we used the hot tub every day. Kitchen was well stocked. We cooked almost every meal and had everything we needed. The office space is a nice, private, comfortable space, as well. "
Modern Mountain Retreat w/ Deck + Hot Tub!

Harpers Ferry Cottage: Hot Tub, WiFi, Dog-Friendly

9.0 out of 10, Wonderful, (8)
"We arrived in 13 degree weather from "
Harpers Ferry Cottage: Hot Tub, WiFi, Dog-Friendly

Mountain Getaway - 7 beds (2 King) - Large Common Area

10.0 out of 10, Exceptional, (9)
"Great place to stay for a family wedding. House was exactly how it was in the photographs. "
Mountain Getaway - 7 beds (2 King) - Large Common Area

Cozy home near Casino, Breweries, Historical attractions, National Park & more

9.8 out of 10, Exceptional, (25)
"Very comfortable home, particularly the beds."
Cozy home near Casino, Breweries, Historical attractions, National Park & more

Shenandoah River-hiking, fishing, wineries, breweries & more

9.6 out of 10, Exceptional, (25)
"This is a very nice house with a lot of space and privacy. It was peaceful drinking coffee on the back porch while watching the deer graze. I would definitely recommend this place for anyone visiting the area"
Shenandoah River-hiking, fishing, wineries, breweries & more

Private Home, Hot Tub, Wifi, Rural Setting, Gas Stove, 70" SmartTV

9.6 out of 10, Exceptional, (11)
"The home was lovely and roomy. Would definitely stay again. The location was perfect to Harpers Ferry and the activities we were interested in."
Private Home, Hot Tub, Wifi, Rural Setting, Gas Stove, 70" SmartTV
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

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (40)
"Nice place! Clean, beautiful, and located just two miles from town. "
The price is SAR 1,032
SAR 1,469 total
includes taxes & fees
8 May - 9 May
18th Century Stone Cottage minutes from historic Middleburg

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

10.0 out of 10, Exceptional, (83)
"The cabin is beautiful and tucked away in the trees. Amazing colors this time of year and was such a great little getaway. Highly recommend staying here!"
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

Cozy Cabin w/ Hot Tub, Arcade & Fire Pit perfect for up to 8 people

9.2 out of 10, Wonderful, (13)
"Week with elderly family members and this home was a good spot to rest and relax. Upon arrival, house was neat and clean. Well stocked with cooking items. Nice layout. Good central locations for day trip options. Overall I would recommend this home. "
Cozy Cabin w/ Hot Tub, Arcade & Fire Pit perfect for up to 8 people
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.