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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
1–6 Aug
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4.94 out of 5 average rating, 179 reviews
Top guest favourite
Cottage in Upperville
Cozy Country Getaway in the Heart of Upperville
4.9 out of 5 average rating, 108 reviews, 2 bedrooms, 3 beds, 2 bathrooms
1–6 Aug
Guest favourite
Home in Upperville
Upperville Hunt Country Cottage
4.91 out of 5 average rating, 207 reviews, 3 bedrooms, 5 beds, 2 bathrooms
1–6 Aug
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
1–6 Aug
Guest favourite
Home in Upperville
Horse Country | Pool | MNT Views | Full Kitchen
4.9 out of 5 average rating, 20 reviews, 6 bedrooms, 8 beds, 6.5 bathrooms
26–31 Aug
Top guest favourite
Guest house in Middleburg
18th Century Middleburg Cottage
5.0 out of 5 average rating, 132 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
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
1–6 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
1–6 Aug
Home in Middleburg
Hunt Country Haven near downtown Middleburg
New place to stay, 4 bedrooms, 4 beds, 2 bathrooms
1–6 Aug
Top guest favourite
Home in Middleburg
English Cottage/Main House
5.0 out of 5 average rating, 54 reviews, 2 bedrooms, 2 beds, 2 bathrooms
1–6 Aug
Top guest favourite
Home in Upperville
Pool|King Bed|Home Theater|Game Room|Wineries
5.0 out of 5 average rating, 6 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Aug
Guest favourite
Home in Middleburg
Grand 9BR Manor Ideal for Weddings & Gatherings
5.0 out of 5 average rating, 7 reviews, 9 bedrooms, 9 beds, 5.5 bathrooms
6–11 Sept
Top guest favourite
Home in Berryville
The Hill House at Stubblefield
4.99 out of 5 average rating, 79 reviews, 2 bedrooms, 3 beds, 2.5 bathrooms
1–6 Aug
Guest favourite
Cottage in Middleburg
Waterfront Cottage at Goose Creek
4.94 out of 5 average rating, 234 reviews, 1 bedroom, 2 beds, 1 bathroom
18–23 Sept
Top guest favourite
Barn in Middleburg
The Hayloft
5.0 out of 5 average rating, 75 reviews, 2 bedrooms, 4 beds, 1.5 bathrooms
23–28 Aug
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
1–6 Aug
Guest favourite
Guest suite in Middleburg
Middleburg Sunset Private Guest Suite
4.9 out of 5 average rating, 20 reviews, 1 bedroom, 2 beds, 1 bathroom
4–9 Aug
Top guest favourite
Cottage in Middleburg
Middleburg Bliss!
5.0 out of 5 average rating, 86 reviews, 3 bedrooms, 5 beds, 2 bathrooms
12–17 Aug
Top guest favourite
Home in Delaplane
Cobbler Mountain Revival | Historic Farmhouse+View
5.0 out of 5 average rating, 38 reviews, 3 bedrooms, 3 beds, 2 bathrooms
11–16 Aug