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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
13–18 Sept
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4.94 out of 5 average rating, 184 reviews
Top guest favourite
Cottage in Upperville
Cozy Country Getaway in the Heart of Upperville
2 bedrooms, 3 beds
30 Oct – 4 Nov
4.9 out of 5 average rating, 109 reviews
Guest favourite
Home in Upperville
Upperville Hunt Country Cottage
3 bedrooms, 5 beds
27 Sept – 2 Oct
4.91 out of 5 average rating, 208 reviews
Top guest favourite
Cottage in Upperville
Green Acre - A Hunt Country Retreat
2 bedrooms, 3 beds
4–9 Oct
4.95 out of 5 average rating, 39 reviews
Guest favourite
Cottage in Upperville
Meticulous Hunt Country 2BR 1BA Upperville Cottage
2 bedrooms, 2 beds
13–18 Sept
4.93 out of 5 average rating, 104 reviews
Guest favourite
Home in Upperville
Reynard's Retreat in Upperville
3 bedrooms, 3 beds
5–10 Oct
4.95 out of 5 average rating, 22 reviews
Guest favourite
Home in Upperville
Horse Country | Pool | MNT Views | Full Kitchen
6 bedrooms, 8 beds
20–25 Sept
4.92 out of 5 average rating, 25 reviews
Top guest favourite
Cottage in Middleburg
Middleburg Bliss!
3 bedrooms, 5 beds
8–13 Dec
5.0 out of 5 average rating, 90 reviews
Top guest favourite
Home in Marshall
Middleburg/Upperville-Stunning,renovated cottage
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.99 out of 5 average rating, 133 reviews
Top guest favourite
Home in Upperville
Pool|King Bed|Home Theater|Game Room|Wineries
1 bedroom, 1 king bed
20–25 Sept
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Upperville
The Upperville Academy
4 bedrooms, 5 beds
20–25 Sept
4.93 out of 5 average rating, 73 reviews
Top guest favourite
Home in Warren County
Ravens' Ridge: Modern Cabin + Stunning Valley View
3 bedrooms, 4 beds
13–18 Sept
5.0 out of 5 average rating, 30 reviews
Guest favourite
Home in Marshall
Middleburg Wine Country Retreat on 135 Acres
3 bedrooms, 3 beds
20–25 Sept
5.0 out of 5 average rating, 12 reviews
Guest favourite
Cottage in Middleburg
Waterfront Cottage at Goose Creek
1 bedroom, 2 beds
2–7 Nov
4.94 out of 5 average rating, 239 reviews
Top guest favourite
Farm stay in Delaplane
Modernized 1880s Farmhouse on 42 Acres
5 bedrooms, 9 beds
26–31 Oct
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Barn in Middleburg
Country Bank Barn
4 bedrooms, 5 beds
13–18 Sept
4.97 out of 5 average rating, 285 reviews
Home in Upperville
Upperville Farm Cottage
2 bedrooms, 2 beds
18–23 Oct
4.86 out of 5 average rating, 7 reviews
Top guest favourite
Barn in Middleburg
Middleburg Carriage House
2 bedrooms, 2 beds
4–9 Oct
4.93 out of 5 average rating, 230 reviews
Top guest favourite
Farm stay in Upperville
Farmhouse, pond & paddock views
4 bedrooms, 5 beds
21–26 Sept
5.0 out of 5 average rating, 15 reviews