Search results; Over 1,000 homes in Upperville

Guest favourite
Cabin in Upperville
Island cabin
1 bedroom, 1 bed, 1 private bathroom
12–17 Jul
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4.94 out of 5 average rating, 175 reviews
Guest favourite
Home in Upperville
Upperville Hunt Country Cottage
3 bedrooms, 5 beds, 2 bathrooms
2–7 Jul
4.91 out of 5 average rating, 206 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, 107 reviews
Top guest favourite
Flat in The Plains
Rose End
1 bedroom, 1 queen bed, 1 bathroom
26–31 Jul
4.98 out of 5 average rating, 698 reviews
Guest favourite
Home in Upperville
Reynard's Retreat in Upperville
3 bedrooms, 3 beds, 2 bathrooms
6–11 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
9–14 Jul
4.94 out of 5 average rating, 36 reviews
Guest favourite
Home in Upperville
Horse Country | Pool | MNT Views | Full Kitchen
6 bedrooms, 8 beds, 6.5 bathrooms
23–28 Aug
4.88 out of 5 average rating, 17 reviews
Top guest favourite
Loft in Purcellville
Saddle Tree at Akeley Wood Farm
1 bedroom, 1 king bed, 1 bathroom
6–11 Jul
4.97 out of 5 average rating, 91 reviews
Top guest favourite
Guest house in Middleburg
18th Century Middleburg Cottage
1 bedroom, 1 queen bed, 1 bathroom
24–29 Jul
5.0 out of 5 average rating, 130 reviews
Top guest favourite
Cottage in Delaplane
Secluded Farm Cottage | 265 Acres of Peace &Nature
2 bedrooms, 2 beds, 1 bathroom
22–27 Jul
5.0 out of 5 average rating, 85 reviews
Top guest favourite
Cabin in Marshall
The Serenity Cabin | Firepit | Wineries | Hiking
1 bedroom, 2 beds, 1.5 bathrooms
15–20 Jul
4.95 out of 5 average rating, 66 reviews
Top guest favourite
Barn in Middleburg
Country Bank Barn
4 bedrooms, 5 beds, 3 bathrooms
1–6 Jul
4.97 out of 5 average rating, 282 reviews
Guest favourite
Cottage in Bluemont
Middleburg/Upperville Country Retreat on Farm
2 bedrooms, 2 single beds, 2.5 bathrooms
7–12 Jul
5.0 out of 5 average rating, 5 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
Guest favourite
Home in Marshall
Atoka Cottage
3 bedrooms, 3 beds, 2 bathrooms
30 Jul – 4 Aug
4.92 out of 5 average rating, 26 reviews
Home in Middleburg
Hunt Country Haven near downtown Middleburg
4 bedrooms, 4 beds, 2 bathrooms
1–6 Jul
New place to stay
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
Guest house in Middleburg
Lovely spacious one-bedroom guest house
1 bedroom, 1 queen bed, 1 bathroom
10–15 Jul
5.0 out of 5 average rating, 110 reviews
Top guest favourite
Farm stay in Upperville
Farmhouse, pond & paddock views
4 bedrooms, 5 beds, 3 bathrooms
6–11 Jul
5.0 out of 5 average rating, 13 reviews