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Search results; Over 1,000 homes in Madison

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Top guest favourite
Home in Madison
Spacious Shenandoah Home on 35 Private Acres
2 bedrooms, 3 beds, 2.5 private bathrooms
12–17 Sept
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4.96 out of 5 average rating, 190 reviews
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Cottage in Madison
THE PERFECT HIKING & WINERY COUNTRY RETREAT
2 bedrooms, 2 queen beds, 1.5 bathrooms
27 Sept – 2 Oct
4.95 out of 5 average rating, 510 reviews
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Guest house in Madison
Madison Farmette Guest House
2 bedrooms, 2 king beds, 1 bathroom
19–24 Oct
4.83 out of 5 average rating, 115 reviews
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Farm stay in Madison
Lucian's Place
3 bedrooms, 3 beds, 2 bathrooms
21–26 Sept
4.99 out of 5 average rating, 84 reviews
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Home in Madison
Downtown Madison Home:Near Wineries and Venues
4 bedrooms, 6 beds, 2.5 bathrooms
21–26 Sept
4.97 out of 5 average rating, 32 reviews
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Farm stay in Madison
Comfortable, scenic farm Living
3 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 201 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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Cottage in Madison
Robinson River Roost - Cottage near Shenandoah NP
2 bedrooms, 3 beds, 1.5 bathrooms
13–18 Sept
4.92 out of 5 average rating, 191 reviews
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Home in Madison
Downtown Madison Studio near Hiking and Venues
1 bathroom
18–23 Sept
4.9 out of 5 average rating, 71 reviews
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Home in Madison
Unit A-Mountain Retreat- SAUNA-Hiking-Wineries
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.95 out of 5 average rating, 487 reviews
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Cabin in Madison
The Cabin at the Lake
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.88 out of 5 average rating, 435 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
4–9 Oct
5.0 out of 5 average rating, 48 reviews
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Guest house in Madison
Hebron Valley Cottage
2 bedrooms, 2 beds, 1 bathroom
14–19 Sept
4.97 out of 5 average rating, 267 reviews
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Farm stay in Madison
Brewery Manor Sleeps 10 Hot Tub
4 bedrooms, 5 beds, 2 bathrooms
8–13 Sept
4.96 out of 5 average rating, 135 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, 89 reviews
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Cottage in Madison
Spectacular Mountain Retreat
2 bedrooms, 3 beds, 1 bathroom
15–20 Sept
4.93 out of 5 average rating, 104 reviews
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Cottage in Madison
Fishback Cottage, Central, Hiking, Wineries
3 bedrooms, 3 beds, 2 bathrooms
20–25 May
4.99 out of 5 average rating, 177 reviews
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Home in Madison
Lakefront Home in Madison
3 bedrooms, 4 beds, 3 bathrooms
7–12 Sept
5.0 out of 5 average rating, 33 reviews
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Tiny home in Madison
Luxury Mountain Tiny Home #2: Sauna, River, Views
1 king bed, 1 bathroom
28 Oct – 2 Nov
5.0 out of 5 average rating, 189 reviews