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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
23–28 Aug
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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
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, 2 bathrooms
18–23 Aug
4.95 out of 5 average rating, 38 reviews
Guest favourite
Home in Upperville
Horse Country | Pool | MNT Views | Full Kitchen
6 bedrooms, 8 beds, 6.5 bathrooms
13–18 Sept
4.9 out of 5 average rating, 21 reviews
Guest favourite
Home in Middleburg
Grand 9BR Manor Ideal for Weddings & Gatherings
9 bedrooms, 9 beds, 5.5 bathrooms
21–26 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Farm stay in Upperville
Farmhouse, pond & paddock views
4 bedrooms, 5 beds, 3 bathrooms
12–17 Aug
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Guest house in Middleburg
18th Century Middleburg Cottage
1 bedroom, 1 queen bed, 1 bathroom
22–27 Aug
5.0 out of 5 average rating, 135 reviews
Top guest favourite
Barn in Middleburg
The Hayloft
2 bedrooms, 4 beds, 1.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 76 reviews
Guest favourite
Home in Upperville
Reynard's Retreat in Upperville
3 bedrooms, 3 beds, 2 bathrooms
19–24 Aug
4.95 out of 5 average rating, 22 reviews
Top guest favourite
Cottage in Middleburg
Middleburg Bliss!
3 bedrooms, 5 beds, 2 bathrooms
19–24 Aug
5.0 out of 5 average rating, 87 reviews
Home in Upperville
Virginia Horse and Wine Country Farm Stay
3 bedrooms, 4 beds, 1 bathroom
15–20 Aug
5.0 out of 5 average rating, 4 reviews
Home in Upperville
Upperville Farm Cottage
2 bedrooms, 2 beds, 2 bathrooms
16–21 Aug
4.75 out of 5 average rating, 4 reviews
Guest favourite
Cabin in Upperville
Island cabin
1 bedroom, 1 queen bed, 1 bathroom
30 Aug – 4 Sept
4.94 out of 5 average rating, 180 reviews
Top guest favourite
Home in Middleburg
English Cottage/Main House
2 bedrooms, 2 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 57 reviews
Top guest favourite
Cabin in Linden
Chipmunk Hollow | Hot Tub, Grill & Fire Table
3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
4.97 out of 5 average rating, 69 reviews
Home in Upperville
Home in Upperville Village
3 bedrooms, 3 beds, No bathroom
11–16 Aug
5.0 out of 5 average rating, 7 reviews
Guest favourite
Cottage in Middleburg
Waterfront Cottage at Goose Creek
1 bedroom, 2 beds, 1 bathroom
2–7 Nov
4.94 out of 5 average rating, 235 reviews
Guest favourite
Cottage in Upperville
Meticulous Hunt Country 2BR 1BA Upperville Cottage
2 bedrooms, 2 beds, 1 bathroom
10–15 Aug
4.93 out of 5 average rating, 102 reviews
Guest favourite
Home in Upperville
The Upperville Academy
4 bedrooms, 5 beds, 3.5 bathrooms
30 Aug – 4 Sept
4.93 out of 5 average rating, 72 reviews