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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
1–6 Aug
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4.9 out of 5 average rating, 108 reviews
Top guest favourite
Cottage in Upperville
Green Acre - A Hunt Country Retreat
4.95 out of 5 average rating, 37 reviews, 2 bedrooms, 3 beds, 2 bathrooms
1–6 Aug
Top guest favourite
Home in Upperville
Pool|King Bed|Home Theater|Game Room|Wineries
5.0 out of 5 average rating, 6 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Aug
Guest favourite
Home in Upperville
Upperville Hunt Country Cottage
4.91 out of 5 average rating, 207 reviews, 3 bedrooms, 5 beds, 2 bathrooms
1–6 Aug
Top guest favourite
Farm stay in Middleburg
The Blacksmith Cottage
4.96 out of 5 average rating, 126 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Guest favourite
Flat in Delaplane
Romantic Wine Country Suite | Polo, Hiking Retreat
5.0 out of 5 average rating, 14 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Guest favourite
Guest suite in Middleburg
Middleburg Sunset Private Guest Suite
4.9 out of 5 average rating, 20 reviews, 1 bedroom, 2 beds, 1 bathroom
4–9 Aug
Home in Upperville
Virginia Horse and Wine Country Farm Stay
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 4 beds, 1 bathroom
1–6 Aug
Guest favourite
Cottage in Upperville
Meticulous Hunt Country 2BR 1BA Upperville Cottage
4.93 out of 5 average rating, 102 reviews, 2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
Top guest favourite
Guest suite in Bluemont
Blueridge Mountain Retreat Apartment
4.93 out of 5 average rating, 659 reviews, 1 bedroom, 2 beds, 1 bathroom
3–8 Aug
Guest favourite
Farm stay in The Plains
Elegant, Country Capsule: Suite and Stone Kitchen
5.0 out of 5 average rating, 8 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Dec
Guest favourite
Cabin in Upperville
Island cabin
4.94 out of 5 average rating, 179 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Guest favourite
Home in Upperville
Reynard's Retreat in Upperville
4.95 out of 5 average rating, 22 reviews, 3 bedrooms, 3 beds, 2 bathrooms
1–6 Aug
Home in Upperville
Upperville Farm Cottage
4.67 out of 5 average rating, 3 reviews, 2 bedrooms, 2 beds, 2 bathrooms
1–6 Aug
Top guest favourite
Loft in Purcellville
Saddle Tree at Akeley Wood Farm
4.97 out of 5 average rating, 94 reviews, 1 bedroom, 1 bed, 1 bathroom
3–8 Aug
Guest favourite
Flat in The Plains
Charming barn apartment in horse /wine country
4.96 out of 5 average rating, 23 reviews, 1 bedroom, 1 bed, 1 bathroom
3–8 Aug
Guest favourite
Cabin in Purcellville
The 1744 Custom Cabin
5.0 out of 5 average rating, 25 reviews, 1 bedroom, 1 bed, 1 bathroom
3–8 Aug
Guest favourite
Home in Marshall
Middleburg Wine Country Retreat on 135 Acres
5.0 out of 5 average rating, 10 reviews, 3 bedrooms, 3 beds, 2 bathrooms
2–7 Aug
Top guest favourite
Farm stay in Middleburg
Retreat to horse country!
4.97 out of 5 average rating, 99 reviews, 1 bedroom, 1 bed, 1.5 bathrooms
9–14 Aug