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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
20–25 Jul
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4.9 out of 5 average rating, 108 reviews
Top guest favourite
Flat in The Plains
Rose End
1 bedroom, 1 queen bed, 1 bathroom
17–22 Aug
4.98 out of 5 average rating, 705 reviews
Guest favourite
Home in Upperville
Upperville Hunt Country Cottage
3 bedrooms, 5 beds, 2 bathrooms
13–18 Jul
4.91 out of 5 average rating, 207 reviews
Top guest favourite
Guest house in Round Hill
Private Carriage House
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
4.97 out of 5 average rating, 503 reviews
Top guest favourite
Loft in Purcellville
Saddle Tree at Akeley Wood Farm
1 bedroom, 1 king bed, 1 bathroom
21–26 Jul
4.97 out of 5 average rating, 92 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, 18 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, 232 reviews
Top guest favourite
Cottage in Upperville
Green Acre - A Hunt Country Retreat
2 bedrooms, 3 beds, 2 bathrooms
15–20 Jul
4.95 out of 5 average rating, 37 reviews
Home in Warren County
Mountain Views w/Hot Tub, 95” TV & Trail Access
3 bedrooms, 4 beds, 3.5 bathrooms
16–21 Aug
New place to stay
Top guest favourite
Home in Marshall
Middleburg/Upperville-Stunning,renovated cottage
2 bedrooms, 3 beds, 2.5 bathrooms
16–21 Jul
4.99 out of 5 average rating, 130 reviews
Guest favourite
Flat in Delaplane
Romantic Wine Country Suite | Polo, Hiking Retreat
1 bedroom, 1 bed, 1 bathroom
12–17 Jul
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Cottage in Bluemont
The Cottage at Stonecroft
2 bedrooms, 2 beds, 1 bathroom
27 Jul – 1 Aug
4.96 out of 5 average rating, 248 reviews
Top guest favourite
Cottage in Delaplane
Secluded Farm Cottage | 265 Acres of Peace &Nature
2 bedrooms, 2 beds, 1 bathroom
21–26 Jul
5.0 out of 5 average rating, 86 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, 130 reviews
Guest favourite
Home in Upperville
Reynard's Retreat in Upperville
3 bedrooms, 3 beds, 2 bathrooms
13–18 Jul
4.95 out of 5 average rating, 22 reviews
Home in Upperville
Upperville Farm Cottage
2 bedrooms, 2 beds, 2 bathrooms
13–18 Jul
Guest favourite
Home in Middleburg
Modern Home on Middleburg Equestrian Farm
3 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
4.96 out of 5 average rating, 213 reviews
Top guest favourite
Cabin in Marshall
The Serenity Cabin | Firepit | Wineries | Hiking
1 bedroom, 2 beds, 1.5 bathrooms
20–25 Jul
4.96 out of 5 average rating, 68 reviews
Top guest favourite
Home in Middleburg
English Cottage/Main House
2 bedrooms, 2 beds, 2 bathrooms
12–17 Jul
5.0 out of 5 average rating, 53 reviews