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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, 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
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
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
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
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
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
Cottage in Middleburg
Middleburg Bliss!
3 bedrooms, 5 beds, 2 bathrooms
21–26 Jul
5.0 out of 5 average rating, 85 reviews
Top guest favourite
Cottage in Berryville
Milton Valley Cottage on Historic Estate Farm
2 bedrooms, 2 beds, 1.5 bathrooms
5–10 Jul
4.98 out of 5 average rating, 115 reviews
Top guest favourite
Farm stay in Middleburg
Fox Hill Farm Retreat
4 bedrooms, 9 beds, 4.5 bathrooms
1–6 Jul
5.0 out of 5 average rating, 23 reviews
Guest favourite
Cottage in Bluemont
Snickers Gap Cottage
1 bedroom, 1 bed, 1 bathroom
27 Jul – 1 Aug
4.99 out of 5 average rating, 168 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
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
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
Cabin in Front Royal
Shenandoah Twilight | Hot Tub + Sunset Views
2 bedrooms, 2 beds, 1 bathroom
5–10 Jul
4.96 out of 5 average rating, 157 reviews
Top guest favourite
Chalet in Bluemont
Emberwood - Hot tub+Sauna+Cold Plunge+Geo Dome
2 bedrooms, 3 beds, 1 bathroom
5–10 Aug
4.99 out of 5 average rating, 75 reviews
Top guest favourite
Cabin in Front Royal
Mountaintop Retreat with Wood Fired Hot Tub
1 bedroom, 1 queen bed, 1 bathroom
18–23 Jul
4.99 out of 5 average rating, 433 reviews
Guest favourite
Home in Middleburg
The Coach Stop at White Hall
4 bedrooms, 4 queen beds, 2 bathrooms
1–6 Jul
4.91 out of 5 average rating, 175 reviews