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SUPERHOST
Entire house
Simpers Retreat House
10 guests3 bedrooms10 beds2 baths
WifiKitchen
SUPERHOST
Entire guesthouse
Skyhorse Retreat Guest House
4 guests1 bedroom2 beds1 bath
Hot tubWifiKitchen
Includes cancellation flexibility
SUPERHOST
Entire house
Mountain Getaway Minutes From Wineries & Hiking!
6 guests2 bedrooms2 beds1 bath
WifiKitchenIndoor fireplace
Includes cancellation flexibility
SUPERHOST
Entire cottage
Meticulous Hunt Country 2BR 1BA Upperville Cottage
3 guests2 bedrooms2 beds1 bath
Kitchen
Includes cancellation flexibility
SUPERHOST
Entire house
The Country French Cottage at High Meadows Estate
4 guests2 bedrooms2 beds1 bath
WifiKitchenIndoor fireplace
SUPERHOST
Entire cottage
The Stone Cottage at Bluemont Vineyard
2 guests1 bedroom1 bed1 bath
WifiKitchen
SUPERHOST
Entire cottage
Upperville Cozy country getaway
5 guests3 bedrooms3 beds1 bath
WifiKitchenIndoor fireplace
Includes cancellation flexibility
SUPERHOST
Private room
Beautiful 18th Century Farm House
2 guests1 bedroom1 bed1 private bath
WifiIndoor fireplace
Includes cancellation flexibility
SUPERHOST
Farm stay
The Cottage at Nestled Inn - Virginia Wine Country
3 guests1 bedroom1 bed1 bath
WifiKitchen
Includes cancellation flexibility
SUPERHOST
Farm stay
Trillium Treehouse
4 guests1 bedroom2 beds1 bath
Kitchen
Includes cancellation flexibility
SUPERHOST
Entire house
Experience Middleburg and the Country Life
8 guests4 bedrooms4 beds2 baths
WifiKitchen
Includes cancellation flexibility
SUPERHOST
Farm stay
Scenic Cottage on Horse Farm
7 guests4 bedrooms4 beds2 baths
Kitchen
Includes cancellation flexibility
SUPERHOST
Entire cottage
The Blue Door Cottage in Wine Country
7 guests4 bedrooms4 beds1.5 baths
WifiKitchenIndoor fireplace
Includes cancellation flexibility
SUPERHOST
Entire house
Little Blue Farmette
6 guests3 bedrooms5 beds2.5 baths
WifiKitchenIndoor fireplace
Includes cancellation flexibility
SUPERHOST
Private room
The Library Suite at Nestled Inn
2 guests1 bedroom1 bed1 private bath
Hot tubWifi
Includes cancellation flexibility
SUPERHOST
Entire cottage
Creekside in Bluemont, VA
6 guests2 bedrooms3 beds1 bath
WifiKitchen
Includes cancellation flexibility
SUPERHOST
Entire cottage
Lanham House - Fully Restored Upperville Gem
6 guests2 bedrooms3 beds2 baths
WifiKitchen
Includes cancellation flexibility
SUPERHOST
Entire guesthouse
Cottage on Horse Farm close to town (10 minutes)
2 guests1 bedroom1 bed1 bath
Kitchen
Includes cancellation flexibility
SUPERHOST
Entire house
Heart of Virginia Wine Country!
12 guests4 bedrooms4 beds3.5 baths
WifiKitchenIndoor fireplace
Includes cancellation flexibility
SUPERHOST
Entire house
SPECTACULAR HOME!-VA Horse, Bike and Wine Country
16+ guests5 bedrooms16 beds3.5 baths
WifiKitchenIndoor fireplace
2140 of 69 places to stay
Enter dates to see full pricing. Additional fees apply. Taxes may be added.