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Search results; Over 1,000 homes in Madison

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Top guest favourite
Cottage in Madison
Spectacular Mountain Retreat
2 bedrooms, 3 beds, 1 private bathroom
22–27 Sept
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4.93 out of 5 average rating, 106 reviews
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Cottage in Madison
THE PERFECT HIKING & WINERY COUNTRY RETREAT
2 bedrooms, 2 queen beds
25–30 Oct
4.95 out of 5 average rating, 515 reviews
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Top guest favourite
Guest house in Madison
Madison Farmette Guest House
2 bedrooms, 2 king beds
27 Sept – 2 Oct
4.84 out of 5 average rating, 117 reviews
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Guest favourite
Home in Madison
Downtown Madison Studio near Hiking and Venues
20–25 Sept
4.9 out of 5 average rating, 73 reviews
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Farm stay in Madison
Lucian's Place
3 bedrooms, 3 beds
24–29 Oct
4.99 out of 5 average rating, 86 reviews
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Top guest favourite
Home in Madison
Unit A-Mountain Retreat- SAUNA-Hiking-Wineries
3 bedrooms, 4 beds
26–31 Oct
4.95 out of 5 average rating, 489 reviews
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Farm stay in Madison
Comfortable, scenic farm Living
3 bedrooms, 4 beds
4–9 Oct
4.98 out of 5 average rating, 204 reviews
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Top guest favourite
Home in Madison
Home with beautiful mountain and river views
6 bedrooms, 9 beds
19–24 Nov
5.0 out of 5 average rating, 91 reviews
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Home in Madison
The Honeysuckle Cottage
4 bedrooms, 6 beds
27 Sept – 2 Oct
4.95 out of 5 average rating, 40 reviews
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Guest favourite
Home in Madison
Downtown Madison Home:Near Wineries and Venues
4 bedrooms, 6 beds
21–26 Sept
4.97 out of 5 average rating, 35 reviews
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Guest favourite
Cottage in Madison
Robinson River Roost - Cottage near Shenandoah NP
2 bedrooms, 3 beds
15–20 Nov
4.91 out of 5 average rating, 194 reviews
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Guest favourite
Home in Madison
Cozy Madison Home near Venues, Wineries, & SNP
4 bedrooms, 5 beds
24–29 Oct
5.0 out of 5 average rating, 25 reviews
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Top guest favourite
Home in Madison
Unit B -Tatum’s Retreat -SAUNA- Hiking-Wineries
2 bedrooms, 4 beds
25–30 Oct
4.94 out of 5 average rating, 332 reviews
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Top guest favourite
Place to stay in Madison
Garage apartment
1 queen bed
20–25 Sept
4.99 out of 5 average rating, 247 reviews
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Top guest favourite
Cottage in Madison
Hebron Valley Sunsets Cottage
2 bedrooms, 2 queen beds
20–25 Sept
5.0 out of 5 average rating, 23 reviews
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Tiny home in Madison
Luxury Mountain Tiny Home #2: Sauna, River, Views
1 king bed
27 Oct – 1 Nov
5.0 out of 5 average rating, 190 reviews
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Top guest favourite
Home in Madison
Blue Ridge Views + Firepit: Oak Hill Overlook
2 bedrooms, 3 beds
3–8 Nov
4.99 out of 5 average rating, 109 reviews
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Top guest favourite
Guest house in Madison
Hebron Valley Cottage
2 bedrooms, 2 beds
26–31 Oct
4.97 out of 5 average rating, 270 reviews
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Top guest favourite
Cabin in Madison
Riverside Cabin in Blue Ridge Mountains sleeps 6
3 bedrooms, 3 beds
20–25 Sept
4.99 out of 5 average rating, 72 reviews