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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
3 bedrooms, 5 beds, 2 bathrooms
9–14 Jul
4.91 out of 5 average rating, 207 reviews
Top guest favourite
Guest house in Middleburg
18th Century Middleburg Cottage
1 bedroom, 1 queen bed, 1 bathroom
2–7 Aug
5.0 out of 5 average rating, 130 reviews
Top guest favourite
Home in Middleburg
English Cottage/Main House
2 bedrooms, 2 beds, 2 bathrooms
9–14 Jul
5.0 out of 5 average rating, 52 reviews
Guest favourite
Home in Upperville
Reynard's Retreat in Upperville
3 bedrooms, 3 beds, 2 bathrooms
9–14 Jul
4.95 out of 5 average rating, 22 reviews
Top guest favourite
Barn in Middleburg
The Hayloft
2 bedrooms, 4 beds, 1.5 bathrooms
22–27 Jul
5.0 out of 5 average rating, 73 reviews
Top guest favourite
Farm stay in Upperville
Farmhouse, pond & paddock views
4 bedrooms, 5 beds, 3 bathrooms
10–15 Jul
5.0 out of 5 average rating, 14 reviews
Guest favourite
Cabin in Upperville
Island cabin
1 bedroom, 1 queen bed, 1 bathroom
12–17 Jul
4.94 out of 5 average rating, 176 reviews
Top guest favourite
Cottage in Middleburg
Middleburg Bliss!
3 bedrooms, 5 beds, 2 bathrooms
21–26 Jul
5.0 out of 5 average rating, 85 reviews
Top guest favourite
Cottage in Upperville
Green Acre - A Hunt Country Retreat
2 bedrooms, 3 beds, 2 bathrooms
11–16 Jul
4.94 out of 5 average rating, 36 reviews
Guest favourite
Cottage in Middleburg
Waterfront Cottage at Goose Creek
1 bedroom, 2 beds, 1 bathroom
11–16 Aug
4.94 out of 5 average rating, 232 reviews
Guest favourite
Home in Upperville
Horse Country | Pool | MNT Views | Full Kitchen
6 bedrooms, 8 beds, 6.5 bathrooms
9–14 Aug
4.88 out of 5 average rating, 17 reviews
Guest favourite
Guest house in Middleburg
Fox Hill Barn Guest Cottage Retreat
1 bedroom, 2 beds, 1 bathroom
19–24 Jul
4.96 out of 5 average rating, 98 reviews
Guest favourite
Cottage in Bluemont
Snickers Gap Cottage
1 bedroom, 1 bed, 1 bathroom
10–15 Aug
4.99 out of 5 average rating, 170 reviews
Home in Upperville
Virginia Horse and Wine Country Farm Stay
3 bedrooms, 4 beds, 1 bathroom
14–19 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Cabin in Front Royal
Mountaintop Retreat with Wood Fired Hot Tub
1 bedroom, 1 queen bed, 1 bathroom
22–27 Jul
4.99 out of 5 average rating, 436 reviews
Top guest favourite
Cottage in Berryville
Milton Valley Cottage on Historic Estate Farm
2 bedrooms, 2 beds, 1.5 bathrooms
12–17 Jul
4.98 out of 5 average rating, 116 reviews
Guest favourite
Home in Middleburg
The Coach Stop at White Hall
4 bedrooms, 4 queen beds, 2 bathrooms
8–13 Jul
4.92 out of 5 average rating, 177 reviews
Top guest favourite
Cottage in Bluemont
The Cottage at Stonecroft
2 bedrooms, 2 beds, 1 bathroom
27 Jul – 1 Aug
4.96 out of 5 average rating, 247 reviews