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Search results; Over 1,000 homes in Upperville

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Guest favourite
Cabin in Upperville
Island cabin
1 bedroom, 1 bed, 1 private bathroom
26 Sept – 1 Oct
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4.94 out of 5 average rating, 186 reviews
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Top guest favourite
Cottage in Upperville
Cozy Country Getaway in the Heart of Upperville
2 bedrooms, 3 beds, 2 bathrooms
30 Oct – 4 Nov
4.9 out of 5 average rating, 110 reviews
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Guest favourite
Home in Upperville
Upperville Hunt Country Cottage
3 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
4.91 out of 5 average rating, 209 reviews
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Guest favourite
Cottage in Upperville
Meticulous Hunt Country 2BR 1BA Upperville Cottage
2 bedrooms, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.93 out of 5 average rating, 104 reviews
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Guest favourite
Home in Upperville
Reynard's Retreat in Upperville
3 bedrooms, 3 beds, 2 bathrooms
2–7 Nov
4.95 out of 5 average rating, 22 reviews
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Top guest favourite
Cottage in Upperville
Green Acre - A Hunt Country Retreat
2 bedrooms, 3 beds, 2 bathrooms
4–9 Oct
4.95 out of 5 average rating, 40 reviews
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Guest favourite
Home in Upperville
Horse Country | Pool | MNT Views | Full Kitchen
6 bedrooms, 8 beds, 6.5 bathrooms
20–25 Sept
4.92 out of 5 average rating, 26 reviews
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Top guest favourite
Home in Upperville
Pool|King Bed|Home Theater|Game Room|Wineries
1 bedroom, 1 king bed, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 8 reviews
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Top guest favourite
Cottage in Middleburg
Middleburg Bliss!
3 bedrooms, 5 beds, 2 bathrooms
8–13 Dec
5.0 out of 5 average rating, 90 reviews
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Top guest favourite
Home in Marshall
Middleburg/Upperville-Stunning,renovated cottage
2 bedrooms, 3 beds, 2.5 bathrooms
16–21 Nov
4.99 out of 5 average rating, 133 reviews
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Guest favourite
Cottage in Middleburg
Waterfront Cottage at Goose Creek
1 bedroom, 2 beds, 1 bathroom
14–19 Dec
4.94 out of 5 average rating, 240 reviews
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Guest favourite
Home in Upperville
The Upperville Academy
4 bedrooms, 5 beds, 3.5 bathrooms
20–25 Sept
4.93 out of 5 average rating, 73 reviews
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Guest favourite
Home in Marshall
Middleburg Wine Country Retreat on 135 Acres
3 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 12 reviews
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Guest favourite
Home in Marshall
Atoka Cottage
3 bedrooms, 3 beds, 2 bathrooms
24–29 Nov
4.9 out of 5 average rating, 30 reviews
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Top guest favourite
Barn in Middleburg
Country Bank Barn
4 bedrooms, 5 beds, 3 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 287 reviews
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Guest favourite
Home in Marshall
Grape & Vine Cottage · Luxury Main Street Retreat
3 bedrooms, 3 beds, 3.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 8 reviews
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Home in Delaplane
Magnolia Hill
3 bedrooms, 3 queen beds, 2.5 bathrooms
21–26 Sept
New place to stay
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Top guest favourite
Farm stay in Delaplane
Modernized 1880s Farmhouse on 42 Acres
5 bedrooms, 9 beds, 4.5 bathrooms
26–31 Oct
5.0 out of 5 average rating, 9 reviews
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Home in Middleburg
Hunt Country Haven near downtown Middleburg
4 bedrooms, 4 beds, 2 bathrooms
21–26 Sept