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Search results; Over 1,000 homes in Upperville

Top guest favourite
Cottage in Upperville
Cozy Country Getaway in the Heart of Upperville
2 bedrooms, 3 beds, 2 private bathrooms
20–25 Jul
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4.9 out of 5 average rating, 108 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
9–14 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
Barn in Middleburg
The Hayloft
5.0 out of 5 average rating, 73 reviews, 2 bedrooms, 4 beds, 1.5 bathrooms
22–27 Jul
Guest favourite
Home in Upperville
Reynard's Retreat in Upperville
4.95 out of 5 average rating, 22 reviews, 3 bedrooms, 3 beds, 2 bathrooms
9–14 Jul
Top guest favourite
Home in Middleburg
English Cottage/Main House
5.0 out of 5 average rating, 52 reviews, 2 bedrooms, 2 beds, 2 bathrooms
9–14 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
10–15 Jul
Guest favourite
Cabin in Upperville
Island cabin
4.94 out of 5 average rating, 176 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Guest favourite
Cottage in Bluemont
Snickers Gap Cottage
4.99 out of 5 average rating, 170 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Aug
Top guest favourite
Cottage in Upperville
Green Acre - A Hunt Country Retreat
4.94 out of 5 average rating, 36 reviews, 2 bedrooms, 3 beds, 2 bathrooms
11–16 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
Cottage in Middleburg
Waterfront Cottage at Goose Creek
4.94 out of 5 average rating, 232 reviews, 1 bedroom, 2 beds, 1 bathroom
11–16 Aug
Top guest favourite
Cottage in Berryville
Milton Valley Cottage on Historic Estate Farm
4.98 out of 5 average rating, 116 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
12–17 Jul
Home in Upperville
Virginia Horse and Wine Country Farm Stay
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 4 beds, 1 bathroom
14–19 Jul
Guest favourite
Home in Upperville
Horse Country | Pool | MNT Views | Full Kitchen
4.88 out of 5 average rating, 17 reviews, 6 bedrooms, 8 beds, 6.5 bathrooms
9–14 Aug
Top guest favourite
Cabin in Front Royal
Mountaintop Retreat with Wood Fired Hot Tub
4.99 out of 5 average rating, 436 reviews, 1 bedroom, 2 beds, 1 bathroom
22–27 Jul
Superhost
Home in Bluemont
NOVA Wine Country Chalet | Fire Pit | 3+ Acres
New place to stay, 3 bedrooms, 3 beds, 2 bathrooms
9–14 Jul
Top guest favourite
Barn in Middleburg
The Studio
4.98 out of 5 average rating, 107 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Jul
Top guest favourite
Farm stay in Middleburg
The Blacksmith Cottage
4.96 out of 5 average rating, 124 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul