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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
12–17 Jul
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4.94 out of 5 average rating, 174 reviews
Guest favourite
Home in Upperville
Upperville Hunt Country Cottage
3 bedrooms, 5 beds, 2 bathrooms
1–6 Jul
4.91 out of 5 average rating, 205 reviews
Top guest favourite
Cottage in Upperville
Cozy Country Getaway in the Heart of Upperville
2 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
4.9 out of 5 average rating, 107 reviews
Guest favourite
Home in Middleburg
Quaker Cottage
2 bedrooms, 3 beds, 1.5 bathrooms
22–27 Jul
4.84 out of 5 average rating, 25 reviews
Home in Middleburg
Hunt Country Haven near downtown Middleburg
4 bedrooms, 4 beds, 2 bathrooms
1–6 Jul
New place to stay
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
Home in Middleburg
English Cottage/Main House
2 bedrooms, 2 beds, 2 bathrooms
1–6 Jul
5.0 out of 5 average rating, 52 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, 129 reviews
Top guest favourite
Barn in Middleburg
The Hayloft
2 bedrooms, 4 beds, 1.5 bathrooms
5–10 Jul
5.0 out of 5 average rating, 72 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, 12 reviews
Top guest favourite
Home in Boyce
Cottage on the Shenandoah
3 bedrooms, 3 beds, 2 bathrooms
5–10 Jul
4.99 out of 5 average rating, 79 reviews
Home in Upperville
Virginia Horse and Wine Country Farm Stay
3 bedrooms, 4 beds, 1 bathroom
1–6 Jul
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Marshall
Middleburg Wine Country Retreat on 135 Acres
3 bedrooms, 3 beds, 2 bathrooms
1–6 Jul
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Berryville
The Hill House at Stubblefield
2 bedrooms, 3 beds, 2.5 bathrooms
5–10 Jul
4.99 out of 5 average rating, 76 reviews
Guest favourite
Cottage in Upperville
Meticulous Hunt Country 2BR 1BA Upperville Cottage
2 bedrooms, 2 beds, 1 bathroom
1–6 Jul
4.93 out of 5 average rating, 102 reviews
Top guest favourite
Cabin in Delaplane
Inglewood - Historic Family Cabin on Working Farm
3 bedrooms, 3 beds, 2 bathrooms
8–13 Jul
5.0 out of 5 average rating, 52 reviews
Top guest favourite
Cottage in Marshall
Garden Oasis outdoor entertainment at FrogPointe.
2 bedrooms, 3 beds, 2 bathrooms
3–8 Jul
4.91 out of 5 average rating, 135 reviews
Top guest favourite
Chalet in Bluemont
Emberwood - Hot tub+Sauna+Cold Plunge+Geo Dome
2 bedrooms, 3 beds, 1 bathroom
8–13 Jul
4.99 out of 5 average rating, 73 reviews
Top guest favourite
Farm stay in Marshall
Charming 3BR Farmhouse • Wine Country Getaway
3 bedrooms, 6 beds, 2.5 bathrooms
6–11 Jul
5.0 out of 5 average rating, 28 reviews