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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
Cottage in Upperville
Meticulous Hunt Country 2BR 1BA Upperville Cottage
2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
4.93 out of 5 average rating, 102 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
Home in Upperville
Virginia Horse and Wine Country Farm Stay
3 bedrooms, 4 beds, 1 bathroom
1–6 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Upperville
Upperville Hunt Country Cottage
3 bedrooms, 5 beds, 2 bathrooms
1–6 Aug
4.91 out of 5 average rating, 207 reviews
Top guest favourite
Guest house in Round Hill
Private Carriage House
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
4.97 out of 5 average rating, 506 reviews
Guest favourite
Home in Upperville
Reynard's Retreat in Upperville
3 bedrooms, 3 beds, 2 bathrooms
1–6 Aug
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 Aug
5.0 out of 5 average rating, 56 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
Home in Apple Mountain Lake
luxury cabin w/ hot tub
3 bedrooms, 4 beds, 1 bathroom
3–8 Aug
New place to stay
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
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
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
Top guest favourite
Home in Boyce
Cottage on the Shenandoah
3 bedrooms, 3 beds, 2 bathrooms
1–6 Aug
4.99 out of 5 average rating, 81 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
Home in Marshall
Middleburg Wine Country Retreat on 135 Acres
3 bedrooms, 3 beds, 2 bathrooms
5–10 Aug
5.0 out of 5 average rating, 10 reviews
Guest favourite
Flat in Delaplane
Romantic Wine Country Suite | Polo, Hiking Retreat
1 bedroom, 1 double bed, 1 bathroom
1–6 Aug
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Cottage in Middleburg
Middleburg Bliss!
3 bedrooms, 5 beds, 2 bathrooms
28 Aug – 2 Sept
5.0 out of 5 average rating, 86 reviews
Top guest favourite
Flat in Middleburg
Middleburg Carriage House Flat Coachman’s Quarters
2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 85 reviews