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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
18–23 Oct
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4.94 out of 5 average rating, 187 reviews
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Home in Upperville
Hatcher Cottage - a romantic country retreat
2 bedrooms, 2 queen beds, 4 bathrooms
21–26 Nov
New place to stay
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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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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, 111 reviews
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Guest favourite
Home in Upperville
The Upperville Academy
4 bedrooms, 5 beds, 3.5 bathrooms
4–9 Oct
4.93 out of 5 average rating, 73 reviews
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Top guest favourite
Home in Upperville
Upperville Hunt Country Cottage
3 bedrooms, 5 beds, 2 bathrooms
4–9 Oct
4.91 out of 5 average rating, 210 reviews
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Guest favourite
Home in Upperville
Reynard's Retreat in Upperville
3 bedrooms, 3 beds, 2 bathrooms
27 Oct – 1 Nov
4.95 out of 5 average rating, 22 reviews
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Top guest favourite
Home in Upperville
Horse Country | Pool | MNT Views | Full Kitchen
6 bedrooms, 8 beds, 6.5 bathrooms
16–21 Oct
4.92 out of 5 average rating, 26 reviews
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Guest favourite
Cottage in Upperville
Meticulous Hunt Country 2BR 1BA Upperville Cottage
2 bedrooms, 2 beds, 1 bathroom
18–23 Oct
4.92 out of 5 average rating, 105 reviews
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Home in Upperville
Upperville Farm Cottage
2 bedrooms, 2 beds, 2 bathrooms
25–30 Oct
4.86 out of 5 average rating, 7 reviews
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Top guest favourite
Farm stay in Upperville
Farmhouse, pond & paddock views
4 bedrooms, 5 beds, 3 bathrooms
1–6 Oct
5.0 out of 5 average rating, 17 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
16–21 Oct
5.0 out of 5 average rating, 8 reviews
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Top guest favourite
Home in Upperville
Virginia Horse and Wine Country Farm Stay
3 bedrooms, 4 beds, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 6 reviews
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Guest favourite
Home in Middleburg
Grand 9BR Manor Ideal for Weddings & Gatherings
9 bedrooms, 9 beds, 5.5 bathrooms
26–31 Oct
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Guest house in Middleburg
18th Century Middleburg Cottage
1 bedroom, 1 queen bed, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 143 reviews
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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 Upperville
Home in Upperville Village ~ close to Show Grounds
3 bedrooms, 3 beds, 2.5 bathrooms
1–6 Oct
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Top guest favourite
Barn in Middleburg
The Hayloft
2 bedrooms, 4 beds, 1.5 bathrooms
2–7 Nov
5.0 out of 5 average rating, 81 reviews
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Guest favourite
Cottage in Paris
Luxe Mountain Escape Near Upperville + Middleburg
1 bedroom, 1 queen bed, 1 bathroom
26–31 Oct
4.97 out of 5 average rating, 359 reviews