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Search results; Over 1,000 homes in Upperville

Descriptions are based on details hosts provide
Guest favourite
Cabin in Upperville
Island cabin
1 bedroom, 1 bed, 1 private bathroom
20–25 Jul
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4.94 out of 5 average rating, 178 reviews
Guest favourite
Home in Upperville
Upperville Hunt Country Cottage
4.91 out of 5 average rating, 207 reviews, 3 bedrooms, 5 beds, 2 bathrooms
16–21 Jul
Top guest favourite
Cottage in Upperville
Green Acre - A Hunt Country Retreat
4.95 out of 5 average rating, 37 reviews, 2 bedrooms, 3 beds, 2 bathrooms
18–23 Jul
Top guest favourite
Cottage in Upperville
English cottage on 2.5 acres of gardens
4.9 out of 5 average rating, 108 reviews, 2 bedrooms, 3 beds, 2 bathrooms
20–25 Jul
Top guest favourite
Guest house in Middleburg
18th Century Middleburg Cottage
5.0 out of 5 average rating, 130 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
Top guest favourite
Home in Middleburg
Renovated farmhouse on 66 peaceful acres
5.0 out of 5 average rating, 53 reviews, 2 bedrooms, 2 beds, 2 bathrooms
26–31 Jul
Top guest favourite
Farm stay in Upperville
Farmhouse, pond & paddock views
5.0 out of 5 average rating, 14 reviews, 4 bedrooms, 5 beds, 3 bathrooms
17–22 Jul
Home in Warren County
Mountain views, hot tub, trail across street
New place to stay, 3 bedrooms, 4 beds, 3.5 bathrooms
16–21 Aug
Guest favourite
Home in Upperville
Hunt box in Virginia wine country
4.95 out of 5 average rating, 22 reviews, 3 bedrooms, 3 beds, 2 bathrooms
16–21 Jul
Top guest favourite
Cottage in Middleburg
Middleburg Bliss!
5.0 out of 5 average rating, 85 reviews, 3 bedrooms, 5 beds, 2 bathrooms
21–26 Jul
Guest favourite
Home in Upperville
4,200 sq ft with pool and fire pit
4.89 out of 5 average rating, 18 reviews, 6 bedrooms, 8 beds, 6.5 bathrooms
9–14 Aug
Guest favourite
Home in Middleburg
Working farm near Middleburg vineyards
4.92 out of 5 average rating, 177 reviews, 4 bedrooms, 4 beds, 2 bathrooms
15–20 Jul
Guest favourite
Cottage in Bluemont
170-year-old cottage with stone walls
4.99 out of 5 average rating, 170 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Aug
Top guest favourite
Cottage in Berryville
18th-century cottage on a historic estate
4.97 out of 5 average rating, 119 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
15–20 Jul
Guest favourite
Cottage in Middleburg
12 acres on Goose Creek with kayaking
4.94 out of 5 average rating, 233 reviews, 1 bedroom, 2 beds, 1 bathroom
11–16 Aug
Guest favourite
Home in Marshall
Middleburg Wine Country Retreat on 135 Acres
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 3 beds, 2 bathrooms
19–24 Jul
Top guest favourite
Barn in Middleburg
The Hayloft
5.0 out of 5 average rating, 73 reviews, 2 bedrooms, 4 beds, 1.5 bathrooms
22–27 Jul
Top guest favourite
Cabin in Front Royal
Wood-fired hot tub above Shenandoah Valley
4.99 out of 5 average rating, 437 reviews, 1 bedroom, 2 beds, 1 bathroom
22–27 Jul
Top guest favourite
Cabin in Linden
Chipmunk Hollow | Hot Tub, Grill & Fire Table
4.97 out of 5 average rating, 66 reviews, 3 bedrooms, 4 beds, 2 bathrooms
26–31 Jul