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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
26–31 Jul
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4.94 out of 5 average rating, 178 reviews
Top guest favourite
Cottage in Upperville
Cozy Country Getaway in the Heart of Upperville
2 bedrooms, 3 beds, 2 bathrooms
20–25 Jul
4.9 out of 5 average rating, 108 reviews
Guest favourite
Home in Upperville
Upperville Hunt Country Cottage
3 bedrooms, 5 beds, 2 bathrooms
21–26 Jul
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
23–28 Jul
4.95 out of 5 average rating, 37 reviews
Guest favourite
Home in Upperville
Horse Country | Pool | MNT Views | Full Kitchen
6 bedrooms, 8 beds, 6.5 bathrooms
9–14 Aug
4.89 out of 5 average rating, 19 reviews
Top guest favourite
Cottage in Middleburg
Middleburg Bliss!
3 bedrooms, 5 beds, 2 bathrooms
21–26 Jul
5.0 out of 5 average rating, 85 reviews
Top guest favourite
Farm stay in Upperville
Farmhouse, pond & paddock views
4 bedrooms, 5 beds, 3 bathrooms
22–27 Jul
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
2–7 Aug
5.0 out of 5 average rating, 132 reviews
Top guest favourite
Barn in Middleburg
The Hayloft
2 bedrooms, 4 beds, 1.5 bathrooms
22–27 Jul
5.0 out of 5 average rating, 73 reviews
Guest favourite
Home in Upperville
Reynard's Retreat in Upperville
3 bedrooms, 3 beds, 2 bathrooms
21–26 Jul
4.95 out of 5 average rating, 22 reviews
Home in Warren County
Mountain Views w/Hot Tub, 95” TV & Trail Access
3 bedrooms, 4 beds, 3.5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Upperville
Pool|King Bed|Home Theater|Game Room|Wineries
1 bedroom, 1 king bed, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Middleburg
English Cottage/Main House
2 bedrooms, 2 beds, 2 bathrooms
26–31 Jul
5.0 out of 5 average rating, 53 reviews
Guest favourite
Home in Middleburg
Grand 9BR Manor Ideal for Weddings & Gatherings
9 bedrooms, 9 beds, 5.5 bathrooms
20–25 Jul
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
11–16 Aug
4.94 out of 5 average rating, 234 reviews
Top guest favourite
Home in Delaplane
Cobbler Mountain Revival | Historic Farmhouse+View
3 bedrooms, 3 beds, 2 bathrooms
11–16 Aug
5.0 out of 5 average rating, 37 reviews
Home in Upperville
Virginia Horse and Wine Country Farm Stay
3 bedrooms, 4 beds, 1 bathroom
21–26 Jul
5.0 out of 5 average rating, 4 reviews
Guest favourite
Cottage in Bluemont
Snickers Gap Cottage
1 bedroom, 1 bed, 1 bathroom
14–19 Aug
4.99 out of 5 average rating, 170 reviews
Top guest favourite
Cabin in Linden
Chipmunk Hollow | Hot Tub, Grill & Fire Table
3 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
4.97 out of 5 average rating, 66 reviews