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Search results; Over 1,000 homes in Brightwood

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Top guest favourite
Chalet in Brightwood
Charming Chalet in Blue Ridge Wine Country
3 bedrooms, 3 beds, 2 private bathrooms
27 Sept – 2 Oct
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4.97 out of 5 average rating, 173 reviews
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Guest suite in Reva
The Log Cabin at Ridgeview - Hiking, Wine, UVA
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.97 out of 5 average rating, 165 reviews
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Home in Culpeper
The Reserve
2 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 94 reviews
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Cottage in Madison
THE PERFECT HIKING & WINERY COUNTRY RETREAT
2 bedrooms, 2 queen beds, 1.5 bathrooms
25–30 Oct
4.95 out of 5 average rating, 515 reviews
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Home in Madison
Home with beautiful mountain and river views
6 bedrooms, 9 beds, 4 bathrooms
19–24 Nov
5.0 out of 5 average rating, 91 reviews
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Home in Robertson
One Of A Kind Home in VA Wine Country on 50 acres
3 bedrooms, 9 beds, 2 bathrooms
27 Sept – 2 Oct
4.93 out of 5 average rating, 261 reviews
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Farm stay in Madison
Lucian's Place
3 bedrooms, 3 beds, 2 bathrooms
24–29 Oct
4.99 out of 5 average rating, 86 reviews
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Flat in Madison
2BR Private Retreat • Near Cville & Wineries
2 bedrooms, 2 beds, 1 bathroom
28 Sept – 3 Oct
New place to stay
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Home in Madison
NEW l Near Shenandoah•Pool•Hot Tub•Fire Pit•10Acre
6 bedrooms, 11 beds, 4.5 bathrooms
18–23 Oct
5.0 out of 5 average rating, 50 reviews
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Flat in Madison
The Studio at Dark Run Retreat
1 bed, 1 bathroom
20–25 Sept
4.91 out of 5 average rating, 277 reviews
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Home in Madison
Spacious Shenandoah Home on 35 Private Acres
2 bedrooms, 3 beds, 2.5 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 192 reviews
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Cabin in Aroda
Spacious log house retreat w/ hot tub & pool table
4 bedrooms, 12 beds, 3 bathrooms
21–26 Sept
4.95 out of 5 average rating, 19 reviews
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Guest house in Madison
Hebron Valley Cottage
2 bedrooms, 2 beds, 1 bathroom
21–26 Sept
4.97 out of 5 average rating, 270 reviews
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Flat in Madison
The Apartment at Dark Run Retreat
1 bedroom, 1 queen bed, 1 bathroom
12–17 Oct
4.97 out of 5 average rating, 230 reviews
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Cabin in Sperryville
Foxfield Cabin
1 bedroom, 2 beds, 1.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 16 reviews
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Home in Madison
Cozy Madison Home near Venues, Wineries, & SNP
4 bedrooms, 5 beds, 2.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 25 reviews
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Cabin in Pratts
Madison County Mountain Retreat Hot Tub& Fireplace
4 bedrooms, 5 beds, 3 bathrooms
9–14 Nov
4.88 out of 5 average rating, 32 reviews
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Farm stay in Madison
Enchanted-Historic Shenandoah Farm
6 bedrooms, 15 beds, 3 bathrooms
4–9 Oct
4.98 out of 5 average rating, 245 reviews
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Guest house in Madison
Madison Farmette Guest House
2 bedrooms, 2 king beds, 1 bathroom
27 Sept – 2 Oct
4.84 out of 5 average rating, 117 reviews