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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
10–15 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
10–15 Jul
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
12–17 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
Farm stay in Upperville
Farmhouse, pond & paddock views
5.0 out of 5 average rating, 14 reviews, 4 bedrooms, 5 beds, 3 bathrooms
11–16 Jul
Guest favourite
Home in Upperville
The Upperville Academy
4.93 out of 5 average rating, 72 reviews, 4 bedrooms, 5 beds, 3.5 bathrooms
30 Aug – 4 Sept
Guest favourite
Cottage in Upperville
Meticulous Hunt Country 2BR 1BA Upperville Cottage
4.93 out of 5 average rating, 102 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 Jul
Guest favourite
Cabin in Upperville
Island cabin
4.94 out of 5 average rating, 177 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 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
Top guest favourite
Cottage in Delaplane
Seaton Place House
5.0 out of 5 average rating, 66 reviews, 3 bedrooms, 3 beds, 2 bathrooms
12–17 Jul
Home in Upperville
Upperville Farm Cottage
2 bedrooms, 2 beds, 2 bathrooms
13–18 Jul
Guest favourite
Cottage in Bluemont
Middleburg/Upperville Country Retreat on Farm
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 2 beds, 2.5 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
Home in Marshall
Middleburg/Upperville-Stunning,renovated cottage
4.99 out of 5 average rating, 129 reviews, 2 bedrooms, 3 beds, 2.5 bathrooms
16–21 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
Top guest favourite
Home in Bluemont
Historic Bluemont Farmhouse
5.0 out of 5 average rating, 30 reviews, 4 bedrooms, 5 beds, 2 bathrooms
25–30 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
Farm stay in Marshall
Charming 3BR Farmhouse • Wine Country Getaway
5.0 out of 5 average rating, 29 reviews, 3 bedrooms, 6 beds, 2.5 bathrooms
12–17 Jul