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Search results; Over 1,000 homes in Brightwood

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Chalet in Brightwood
Charming Chalet in Blue Ridge Wine Country
3 bedrooms, 3 beds, 2 private bathrooms
18–23 Oct
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4.97 out of 5 average rating, 174 reviews
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Guest suite in Reva
The Log Cabin at Ridgeview - Hiking, Wine, UVA
3 bedrooms, 4 beds, 2 bathrooms
11–16 Oct
4.97 out of 5 average rating, 166 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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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, 516 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 Culpeper
The Reserve
2 bedrooms, 5 beds, 2 bathrooms
8–13 Nov
5.0 out of 5 average rating, 94 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
1–6 Nov
4.93 out of 5 average rating, 261 reviews
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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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Home in Madison
The Honeysuckle Cottage
4 bedrooms, 6 beds, 2 bathrooms
18–23 Oct
4.95 out of 5 average rating, 40 reviews
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Cabin in Aroda
Spacious log house retreat w/ hot tub & pool table
4 bedrooms, 12 beds, 3 bathrooms
16–21 Nov
4.95 out of 5 average rating, 19 reviews
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Flat in Madison
The Studio at Dark Run Retreat
1 bed, 1 bathroom
4–9 Oct
4.91 out of 5 average rating, 277 reviews
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Guest house in Madison
Hebron Valley Cottage
2 bedrooms, 2 beds, 1 bathroom
26–31 Oct
4.97 out of 5 average rating, 271 reviews
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Home in Madison
Spacious Shenandoah Home on 35 Private Acres
2 bedrooms, 3 beds, 2.5 bathrooms
12–17 Oct
4.96 out of 5 average rating, 192 reviews
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Home in Madison
Cozy Madison Home near Venues, Wineries, & SNP
4 bedrooms, 5 beds, 2.5 bathrooms
24–29 Oct
5.0 out of 5 average rating, 25 reviews
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Home in Aroda
The Henhouse at Castlebrook Estate
3 bedrooms, 6 beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 3 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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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, 33 reviews
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Cabin in Haywood
Between the Peaks Dogs Welcome! *Hottub*
2 bedrooms, 2 queen beds, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 61 reviews
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Home in Madison
White Rock Escape
3 bedrooms, 5 beds, 2 bathrooms
18–23 Oct
4.98 out of 5 average rating, 61 reviews