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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
20–25 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
4.9 out of 5 average rating, 108 reviews, 2 bedrooms, 3 beds, 2 bathrooms
20–25 Jul
Guest favourite
Home in Upperville
Upperville Hunt Country Cottage
4.91 out of 5 average rating, 207 reviews, 3 bedrooms, 5 beds, 2 bathrooms
14–19 Jul
Top guest favourite
Flat in The Plains
Rose End
4.98 out of 5 average rating, 705 reviews, 1 bedroom, 1 bed, 1 bathroom
17–22 Aug
Guest favourite
Home in Upperville
Horse Country | Pool | MNT Views | Full Kitchen
4.89 out of 5 average rating, 18 reviews, 6 bedrooms, 8 beds, 6.5 bathrooms
9–14 Aug
Top guest favourite
Cottage in Upperville
Green Acre - A Hunt Country Retreat
4.95 out of 5 average rating, 37 reviews, 2 bedrooms, 3 beds, 2 bathrooms
16–21 Jul
Top guest favourite
Guest house in Round Hill
Private Carriage House
4.97 out of 5 average rating, 503 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Aug
Top guest favourite
Loft in Purcellville
Saddle Tree at Akeley Wood Farm
4.97 out of 5 average rating, 92 reviews, 1 bedroom, 1 bed, 1 bathroom
21–26 Jul
Guest favourite
Cottage in Middleburg
Waterfront Cottage at Goose Creek
4.94 out of 5 average rating, 233 reviews, 1 bedroom, 2 beds, 1 bathroom
11–16 Aug
Guest favourite
Home in Upperville
Reynard's Retreat in Upperville
4.95 out of 5 average rating, 22 reviews, 3 bedrooms, 3 beds, 2 bathrooms
14–19 Jul
Top guest favourite
Home in Marshall
Middleburg/Upperville-Stunning,renovated cottage
4.99 out of 5 average rating, 130 reviews, 2 bedrooms, 3 beds, 2.5 bathrooms
16–21 Jul
Top guest favourite
Guest house in Middleburg
18th Century Middleburg Cottage
5.0 out of 5 average rating, 130 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
Top guest favourite
Cottage in Bluemont
The Cottage at Stonecroft
4.96 out of 5 average rating, 248 reviews, 2 bedrooms, 2 beds, 1 bathroom
27 Jul – 1 Aug
Top guest favourite
Cottage in Delaplane
Secluded Farm Cottage | 265 Acres of Peace &Nature
5.0 out of 5 average rating, 86 reviews, 2 bedrooms, 2 beds, 1 bathroom
21–26 Jul
Top guest favourite
Cabin in Marshall
The Serenity Cabin | Firepit | Wineries | Hiking
4.96 out of 5 average rating, 68 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
20–25 Jul
Top guest favourite
Farm stay in Delaplane
Modernized 1880s Farmhouse on 42 Acres
5.0 out of 5 average rating, 8 reviews, 5 bedrooms, 9 beds, 4.5 bathrooms
16–21 Jul
Guest favourite
Home in Middleburg
Modern Home on Middleburg Equestrian Farm
4.96 out of 5 average rating, 213 reviews, 3 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
Top guest favourite
Barn in Middleburg
Country Bank Barn
4.97 out of 5 average rating, 282 reviews, 4 bedrooms, 5 beds, 3 bathrooms
13–18 Jul
Guest favourite
Flat in Delaplane
Romantic Wine Country Suite | Polo, Hiking Retreat
5.0 out of 5 average rating, 14 reviews, 1 bedroom, 1 bed, 1 bathroom
14–19 Jul