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Search results; Over 1,000 homes in Madison

Top guest favourite
Cabin in Madison
Log Cabin at Ragged Rock Ridge
3 bedrooms, 3 beds, 2 shared baths
Aug 13–18
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5.0 out of 5 average rating, 163 reviews
Guest favourite
Guesthouse in Madison
Madison Farmette Guest House
2 bedrooms, 2 king beds, 1 bath
Aug 16–21
4.83 out of 5 average rating, 112 reviews
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Home in Madison
Downtown Madison Studio near Hiking and Venues
1 bath
Aug 16–21
4.9 out of 5 average rating, 69 reviews
Guest favourite
Home in Madison
Downtown Madison Home:Near Wineries and Venues
4 bedrooms, 6 beds, 2.5 baths
Aug 25–30
4.97 out of 5 average rating, 32 reviews
Top guest favourite
Cottage in Madison
THE PERFECT HIKING & WINERY COUNTRY RETREAT
2 bedrooms, 2 queen beds, 1.5 baths
Sep 20–25
4.95 out of 5 average rating, 506 reviews
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Farm stay in Madison
Comfortable, scenic farm Living
3 bedrooms, 4 beds, 2 baths
Aug 15–20
4.97 out of 5 average rating, 199 reviews
Top guest favourite
Farm stay in Madison
Lucian's Place
3 bedrooms, 3 beds, 2 baths
Sep 21–26
4.99 out of 5 average rating, 82 reviews
Guest favourite
Cottage in Madison
Robinson River Roost - Cottage near Shenandoah NP
2 bedrooms, 3 beds, 1.5 baths
Sep 13–18
4.92 out of 5 average rating, 186 reviews
Top guest favourite
Apartment in Madison
The Studio at Dark Run Retreat
1 bed, 1 bath
Aug 14–19
4.91 out of 5 average rating, 273 reviews
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Tiny homes in Madison
Luxury Mountain Tiny Home #2: Sauna, River, Views
1 king bed, 1 bath
Aug 16–21
5.0 out of 5 average rating, 186 reviews
Top guest favourite
Guesthouse in Madison
Hebron Valley Cottage
2 bedrooms, 2 beds, 1 bath
Aug 13–18
4.97 out of 5 average rating, 266 reviews
Top guest favourite
Cottage in Madison
Spectacular Mountain Retreat
2 bedrooms, 3 beds, 1 bath
Aug 14–19
4.93 out of 5 average rating, 104 reviews
Top guest favourite
Home in Madison
Cozy Madison Home near Venues, Wineries, & SNP
4 bedrooms, 5 beds, 2.5 baths
Sep 20–25
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Home in Madison
Unit A-Mountain Retreat- SAUNA-Hiking-Wineries
3 bedrooms, 4 beds, 2 baths
Aug 23–28
4.95 out of 5 average rating, 485 reviews
Top guest favourite
Place to stay in Madison
Garage apartment
1 queen bed, 1 bath
Aug 13–18
4.99 out of 5 average rating, 247 reviews
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Home in Madison
Lakefront Home in Madison
3 bedrooms, 4 beds, 3 baths
Aug 16–21
5.0 out of 5 average rating, 31 reviews
Top guest favourite
Farm stay in Madison
Brewery Manor Sleeps 10 Hot Tub
4 bedrooms, 5 beds, 2 baths
Sep 8–13
4.95 out of 5 average rating, 132 reviews
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Apartment in Madison
The Apartment at Dark Run Retreat
1 bedroom, 1 queen bed, 1 bath
Aug 15–20
4.97 out of 5 average rating, 229 reviews
Top guest favourite
Home in Madison
NEW l Near Shenandoah•Pool•Hot Tub•Fire Pit•10Acre
6 bedrooms, 11 beds, 4.5 baths
Oct 4–9
5.0 out of 5 average rating, 45 reviews