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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
Guest favourite
Home in Upperville
Upperville Hunt Country Cottage
3 bedrooms, 5 beds, 2 bathrooms
8–13 Jul
4.91 out of 5 average rating, 207 reviews
Guest favourite
Home in Upperville
Horse Country | Pool | MNT Views | Full Kitchen
6 bedrooms, 8 beds, 6.5 bathrooms
9–14 Aug
4.88 out of 5 average rating, 17 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
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
Guest favourite
Home in Upperville
Reynard's Retreat in Upperville
3 bedrooms, 3 beds, 2 bathrooms
8–13 Jul
4.95 out of 5 average rating, 22 reviews
Top guest favourite
Cottage in Upperville
Green Acre - A Hunt Country Retreat
2 bedrooms, 3 beds, 2 bathrooms
10–15 Jul
4.94 out of 5 average rating, 36 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, 700 reviews
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, 129 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, 502 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, 91 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
Cottage in Bluemont
The Cottage at Stonecroft
2 bedrooms, 2 beds, 1 bathroom
27 Jul – 1 Aug
4.96 out of 5 average rating, 246 reviews
Top guest favourite
Farm stay in Marshall
Charming 3BR Farmhouse • Wine Country Getaway
3 bedrooms, 6 beds, 2.5 bathrooms
7–12 Jul
5.0 out of 5 average rating, 28 reviews
Guest favourite
Cabin in Upperville
Island cabin
1 bedroom, 1 queen bed, 1 bathroom
12–17 Jul
4.94 out of 5 average rating, 176 reviews
Top guest favourite
Barn in Middleburg
Country Bank Barn
4 bedrooms, 5 beds, 3 bathrooms
7–12 Jul
4.97 out of 5 average rating, 282 reviews
Top guest favourite
Cabin in Marshall
The Serenity Cabin | Firepit | Wineries | Hiking
1 bedroom, 2 beds, 1.5 bathrooms
15–20 Jul
4.96 out of 5 average rating, 68 reviews
Top guest favourite
Farm stay in Upperville
Farmhouse, pond & paddock views
4 bedrooms, 5 beds, 3 bathrooms
9–14 Jul
5.0 out of 5 average rating, 14 reviews
Guest favourite
Home in Marshall
Josephine's Cottage: Peaceful Getaway Near DC
3 bedrooms, 3 beds, 2 bathrooms
8–13 Jul
5.0 out of 5 average rating, 8 reviews