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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
13–18 Sept
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4.94 out of 5 average rating, 184 reviews
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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, 108 reviews
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Guest favourite
Home in Upperville
Upperville Hunt Country Cottage
3 bedrooms, 5 beds, 2 bathrooms
27 Sept – 2 Oct
4.91 out of 5 average rating, 207 reviews
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Home in Upperville
Horse Country | Pool | MNT Views | Full Kitchen
6 bedrooms, 8 beds, 6.5 bathrooms
13–18 Sept
4.92 out of 5 average rating, 24 reviews
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Cottage in Upperville
Green Acre - A Hunt Country Retreat
2 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
4.95 out of 5 average rating, 38 reviews
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Cottage in Upperville
Meticulous Hunt Country 2BR 1BA Upperville Cottage
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.93 out of 5 average rating, 102 reviews
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Home in Upperville
The Upperville Academy
4 bedrooms, 5 beds, 3.5 bathrooms
20–25 Sept
4.93 out of 5 average rating, 72 reviews
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Home in Upperville
Reynard's Retreat in Upperville
3 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
4.95 out of 5 average rating, 22 reviews
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Home in Marshall
Middleburg/Upperville-Stunning,renovated cottage
2 bedrooms, 3 beds, 2.5 bathrooms
27 Sept – 2 Oct
4.99 out of 5 average rating, 131 reviews
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Cottage in Middleburg
Waterfront Cottage at Goose Creek
1 bedroom, 2 beds, 1 bathroom
2–7 Nov
4.94 out of 5 average rating, 238 reviews
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Home in Marshall
Grape & Vine Cottage · Luxury Main Street Retreat
3 bedrooms, 3 beds, 3.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 8 reviews
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Home in Middleburg
Peaceful, Authentic Stone Cottage with Cozy Charm
3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
4.94 out of 5 average rating, 88 reviews
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Loft in Purcellville
Saddle Tree at Akeley Wood Farm
1 bedroom, 1 king bed, 1 bathroom
12–17 Sept
4.97 out of 5 average rating, 97 reviews
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Home in Upperville
Home in Upperville Village
3 bedrooms, 3 beds, No bathroom
1–6 Sept
5.0 out of 5 average rating, 7 reviews
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Home in Middleburg
Hunt Country Haven near downtown Middleburg
4 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
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Guest suite in Markham
"The Love Nest" - Stunning Views in Wine Country!
1 bedroom, 1 queen bed, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 133 reviews
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Cottage in Middleburg
English Cottage
1 bedroom, 2 beds, 1 bathroom
25–30 Oct
4.93 out of 5 average rating, 154 reviews
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Barn in Middleburg
Country Bank Barn
4 bedrooms, 5 beds, 3 bathrooms
13–18 Sept
4.97 out of 5 average rating, 284 reviews
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Guest house in Round Hill
Private Carriage House
1 bedroom, 1 queen bed, 1 bathroom
8–13 Nov
4.97 out of 5 average rating, 507 reviews