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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
2–7 Aug
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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
3–8 Aug
4.91 out of 5 average rating, 207 reviews
Top guest favourite
Cottage in Upperville
Green Acre - A Hunt Country Retreat
2 bedrooms, 3 beds, 2 bathrooms
10–15 Aug
4.95 out of 5 average rating, 37 reviews
Guest favourite
Cottage in Upperville
Meticulous Hunt Country 2BR 1BA Upperville Cottage
2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
4.93 out of 5 average rating, 102 reviews
Guest favourite
Home in Upperville
Reynard's Retreat in Upperville
3 bedrooms, 3 beds, 2 bathrooms
3–8 Aug
4.95 out of 5 average rating, 22 reviews
Guest favourite
Cabin in Upperville
Island cabin
1 bedroom, 1 queen bed, 1 bathroom
2–7 Aug
4.94 out of 5 average rating, 180 reviews
Top guest favourite
Guest house in Round Hill
Private Carriage House
1 bedroom, 1 queen bed, 1 bathroom
22–27 Aug
4.97 out of 5 average rating, 506 reviews
Home in Upperville
Upperville Farm Cottage
2 bedrooms, 2 beds, 2 bathrooms
2–7 Aug
4.67 out of 5 average rating, 3 reviews
Top guest favourite
Guest suite in Bluemont
Blueridge Mountain Retreat Apartment
1 bedroom, 2 beds, 1 bathroom
17–22 Aug
4.93 out of 5 average rating, 660 reviews
Top guest favourite
Guest house in Middleburg
18th Century Middleburg Cottage
1 bedroom, 1 queen bed, 1 bathroom
21–26 Aug
5.0 out of 5 average rating, 132 reviews
Top guest favourite
Loft in Purcellville
Saddle Tree at Akeley Wood Farm
1 bedroom, 1 king bed, 1 bathroom
3–8 Aug
4.97 out of 5 average rating, 94 reviews
Guest favourite
Flat in The Plains
Charming barn apartment in horse /wine country
1 bedroom, 1 double bed, 1 bathroom
3–8 Aug
4.96 out of 5 average rating, 23 reviews
Guest favourite
Room in Bluemont
A Castle in the Woods at Bluemont VIrginia
5 beds, 1.5 bathrooms
22–27 Aug
4.91 out of 5 average rating, 376 reviews
Top guest favourite
Flat in Middleburg
Middleburg Carriage House Studio - The Loft
1 bedroom, 1 queen bed, 1 bathroom
14–19 Aug
5.0 out of 5 average rating, 23 reviews
Guest favourite
Cottage in Paris
Luxe Mountain Escape Near Upperville + Middleburg
1 bedroom, 1 queen bed, 1 bathroom
10–15 Aug
4.97 out of 5 average rating, 357 reviews
Top guest favourite
Farm stay in Upperville
Farmhouse, pond & paddock views
4 bedrooms, 5 beds, 3 bathrooms
4–9 Aug
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Boyce
Cottage on the Shenandoah
3 bedrooms, 3 beds, 2 bathrooms
2–7 Aug
4.99 out of 5 average rating, 81 reviews
Home in Upperville
Virginia Horse and Wine Country Farm Stay
3 bedrooms, 4 beds, 1 bathroom
3–8 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Cottage in Bluemont
The Cottage at Stonecroft
2 bedrooms, 2 beds, 1 bathroom
2–7 Nov
4.96 out of 5 average rating, 251 reviews