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Search results; Over 1,000 homes in Upperville

Guest favourite
Cabin in Upperville
Island cabin
1 bedroom, 1 bed, 1 private bathroom
30 Aug – 4 Sept
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4.94 out of 5 average rating, 180 reviews
Top guest favourite
Cottage in Upperville
Cozy Country Getaway in the Heart of Upperville
2 bedrooms, 3 beds
23–28 Aug
4.9 out of 5 average rating, 108 reviews
Guest favourite
Home in Upperville
Upperville Hunt Country Cottage
3 bedrooms, 5 beds
19–24 Aug
4.91 out of 5 average rating, 207 reviews
Top guest favourite
Cottage in Upperville
Green Acre - A Hunt Country Retreat
2 bedrooms, 3 beds
11–16 Aug
4.95 out of 5 average rating, 38 reviews
Guest favourite
Cottage in Upperville
Meticulous Hunt Country 2BR 1BA Upperville Cottage
2 bedrooms, 2 beds
8–13 Aug
4.93 out of 5 average rating, 102 reviews
Guest favourite
Home in Upperville
Reynard's Retreat in Upperville
3 bedrooms, 3 beds
19–24 Aug
4.95 out of 5 average rating, 22 reviews
Top guest favourite
Guest house in Middleburg
18th Century Middleburg Cottage
1 bedroom, 1 queen bed
22–27 Aug
5.0 out of 5 average rating, 134 reviews
Guest favourite
Home in Upperville
Horse Country | Pool | MNT Views | Full Kitchen
6 bedrooms, 8 beds
13–18 Sept
4.9 out of 5 average rating, 20 reviews
Guest favourite
Home in Upperville
The Upperville Academy
4 bedrooms, 5 beds
30 Aug – 4 Sept
4.93 out of 5 average rating, 72 reviews
Home in Upperville
Upperville Farm Cottage
2 bedrooms, 2 beds
14–19 Aug
4.67 out of 5 average rating, 3 reviews
Home in Upperville
Virginia Horse and Wine Country Farm Stay
3 bedrooms, 4 beds
15–20 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Guest suite in Middleburg
Middleburg Sunset Private Guest Suite
1 bedroom, 2 beds
11–16 Aug
4.9 out of 5 average rating, 21 reviews
Top guest favourite
Farm stay in Upperville
Farmhouse, pond & paddock views
4 bedrooms, 5 beds
10–15 Aug
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Cottage in Middleburg
Middleburg Bliss!
3 bedrooms, 5 beds
19–24 Aug
5.0 out of 5 average rating, 87 reviews
Guest favourite
Home in Marshall
Atoka Cottage
3 bedrooms, 3 beds
16–21 Aug
4.89 out of 5 average rating, 28 reviews
Top guest favourite
Cottage in Bluemont
Snickers Gap Cottage
1 bedroom, 1 bed
9–14 Dec
4.99 out of 5 average rating, 172 reviews
Top guest favourite
Barn in Middleburg
The Studio
1 bedroom, 1 king bed
18–23 Aug
4.98 out of 5 average rating, 107 reviews
Top guest favourite
Flat in The Plains
Rose End
1 bedroom, 1 queen bed
30 Aug – 4 Sept
4.98 out of 5 average rating, 713 reviews
Top guest favourite
Barn in Middleburg
The Hayloft
2 bedrooms, 4 beds
23–28 Aug
5.0 out of 5 average rating, 76 reviews