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Search results; 185 homes in Madison

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Guest favourite
Home in Madison
Glenda’s Overlook
2 bedrooms, 3 beds, 2 shared bathrooms
1–6 Nov
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4.96 out of 5 average rating, 112 reviews
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Top guest favourite
Cottage in Madison
3-suite cottage spa (aaaah!) house
3 bedrooms, 4 beds, 3 bathrooms
16–21 Oct
4.99 out of 5 average rating, 70 reviews
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Home in Madison
A walk in the parks
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
New place to stay
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Top guest favourite
Home in Madison
Charming shotgun in the heart of downtown Madison
2 bedrooms, 3 beds, 2 bathrooms
7–12 Dec
5.0 out of 5 average rating, 257 reviews
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Top guest favourite
Home in Madison
Coming Home Cottage
1 bedroom, 2 beds, 1 bathroom
26–31 Oct
4.98 out of 5 average rating, 59 reviews
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Guest favourite
Townhouse in Madison
"Madison Manor I" •Hot Tub •Game Room •Sleeps 8
3 bedrooms, 4 beds, 2 bathrooms
26–31 Oct
4.86 out of 5 average rating, 49 reviews
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Guest favourite
Home in Hanover
The Hanover O-Asis
3 bedrooms, 3 beds, 2 bathrooms
12–17 Oct
4.85 out of 5 average rating, 13 reviews
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Guest favourite
Home in Milton
The Porch at Milton
2 bedrooms, 2 beds, 2.5 bathrooms
1–6 Oct
4.93 out of 5 average rating, 45 reviews
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Guest favourite
Home in Madison
Jefferson Off Main: *4 Beds*King Beds*Walk to Main
4 bedrooms, 4 beds, 3 bathrooms
11–16 Oct
4.92 out of 5 average rating, 79 reviews
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Guest favourite
Cabin in Madison
Wolf Creek Cabin Wildlife/10 min to town/sleeps 12
4 bedrooms, 5 beds, 2 bathrooms
4–9 Oct
4.95 out of 5 average rating, 132 reviews
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Superhost
Hotel in Madison
East Main Lofts - Haven 202
1 bedroom, 1 bed, 1 bathroom
18–23 Oct
4.82 out of 5 average rating, 28 reviews
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Home in Madison
Rooftop on Main
1 bedroom, 2 beds, 1 bathroom
30 Oct – 4 Nov
New place to stay
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Guest favourite
Cabin in Madison
Walnut Woodland Cabin at Lost Trails
2 bedrooms, 1 queen bed, 1 bathroom
11–16 Oct
4.96 out of 5 average rating, 27 reviews
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Home in Hanover
The Hanover Haven - Slice of Paradise
3 bedrooms, 4 beds, 2.5 bathrooms
4–9 Oct
4.82 out of 5 average rating, 34 reviews
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Houseboat in Madison
Madison Regatta 2026
5 bedrooms, 7 beds, 2 bathrooms
1–6 Oct
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Home in Madison
Eleonora's Cottage On Main
3 bedrooms, 4 beds, 1 bathroom
11–16 Oct
4.5 out of 5 average rating, 147 reviews
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Guest favourite
Flat in Madison
The Madison Inn, Est 1925 Historic suite 107
1 bedroom, 2 beds, 1 bathroom
25–30 Oct
4.93 out of 5 average rating, 59 reviews
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Top guest favourite
Home in Madison
Riverview Historical Retreat
2 bedrooms, 2 queen beds, 2 bathrooms
4–9 Oct
4.97 out of 5 average rating, 231 reviews
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Top guest favourite
Flat in Madison
Dragonfly Suite -Bohemian Decor-
1 bedroom, 2 queen beds, 1 bathroom
4–9 Oct
4.97 out of 5 average rating, 621 reviews