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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
30 Oct – 4 Nov
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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
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, 103 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, 24 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
The Upperville Academy
4 bedrooms, 5 beds
20–25 Sept
4.93 out of 5 average rating, 72 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
Guest favourite
Cabin in Upperville
Island cabin
1 bedroom, 1 queen bed
13–18 Sept
4.94 out of 5 average rating, 184 reviews
Home in Upperville
Virginia Horse and Wine Country Farm Stay
3 bedrooms, 4 beds
26 Sept – 1 Oct
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Barn in Middleburg
The Hayloft
2 bedrooms, 4 beds
20–25 Sept
5.0 out of 5 average rating, 79 reviews
Home in Upperville
Home in Upperville Village
3 bedrooms, 3 beds
7–12 Sept
5.0 out of 5 average rating, 7 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 Middleburg
Grand 9BR Manor Ideal for Weddings & Gatherings
9 bedrooms, 9 beds
6–11 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Cottage in Delaplane
Seaton Place House
3 bedrooms, 3 beds
4–9 Oct
5.0 out of 5 average rating, 68 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
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
Guest house in Middleburg
18th Century Middleburg Cottage
1 bedroom, 1 queen bed
25–30 Oct
5.0 out of 5 average rating, 141 reviews
Top guest favourite
Home in Boyce
Cottage on the Shenandoah
3 bedrooms, 2 beds
27 Sept – 2 Oct
4.99 out of 5 average rating, 84 reviews