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Search results; Over 1,000 homes in Upperville

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Top guest favourite
Cottage in Upperville
Cozy Country Getaway in the Heart of Upperville
2 bedrooms, 3 beds, 2 private bathrooms
30 Oct – 4 Nov
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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, 210 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
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
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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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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Top guest favourite
Farm stay in Upperville
Farmhouse, pond & paddock views
4 bedrooms, 5 beds, 3 bathrooms
21–26 Sept
5.0 out of 5 average rating, 16 reviews
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Guest favourite
Cabin in Upperville
Island cabin
1 bedroom, 1 queen bed, 1 bathroom
26 Sept – 1 Oct
4.94 out of 5 average rating, 186 reviews
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Home in Upperville
Upperville Farm Cottage
2 bedrooms, 2 beds, 2 bathrooms
18–23 Oct
4.86 out of 5 average rating, 7 reviews
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Home in Upperville
Virginia Horse and Wine Country Farm Stay
3 bedrooms, 4 beds, 1 bathroom
26 Sept – 1 Oct
5.0 out of 5 average rating, 4 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
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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Home in Upperville
Home in Upperville Village
3 bedrooms, 3 beds, No bathroom
20–25 Sept
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Barn in Middleburg
The Hayloft
2 bedrooms, 4 beds, 1.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 81 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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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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Top guest favourite
Villa in Middleburg
Fox Hill Farm Retreat
4 bedrooms, 9 beds, 4.5 bathrooms
12–17 Oct
5.0 out of 5 average rating, 28 reviews
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Top guest favourite
Cottage in Delaplane
Seaton Place House
3 bedrooms, 3 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 69 reviews