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Search results; Over 1,000 homes in Madison

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Top guest favourite
Farm stay in Madison
Madison Nature Getaway
1 bedroom, 2 beds, 1 private bathroom
9–14 Nov
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4.98 out of 5 average rating, 228 reviews
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Top guest favourite
Home in Woolford
Gorgeous Waterfront, Beach, Pool, Pets- 7 Bd /5ba
7 bedrooms, 13 beds, 5 bathrooms
21–26 Sept
4.98 out of 5 average rating, 90 reviews
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Top guest favourite
Home in Woolford
Starboard on McKeil Point, w/heated pool & hot tub
6 bedrooms, 11 beds, 4.5 bathrooms
28 Sept – 3 Oct
4.99 out of 5 average rating, 144 reviews
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Top guest favourite
Home in Madison
Madison Bay Club House
3 bedrooms, 7 beds, 2.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 54 reviews
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Guest favourite
Home in Woolford
"Endless Summer" on the Chesapeake!
4 bedrooms, 7 beds, 2.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 8 reviews
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Home in Cambridge
Amazing Everything!
4 bedrooms, 4 beds, 4.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 3 reviews
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Home in Cambridge
Family and Pet-Friendly, Waterfront with Pier
4 bedrooms, 5 beds, 1.5 bathrooms
27 Sept – 2 Oct
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Flat in Cambridge
Lairds Cove
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
New place to stay
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Home in Madison
Madison Bay Retreat
2 bedrooms, 2 beds, 2 bathrooms
22–27 Sept
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Guest favourite
Place to stay in Cambridge
Wye Three Oaks
2 bedrooms, 4 beds, 1 bathroom
25–30 Sept
4.95 out of 5 average rating, 110 reviews
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Home in Madison
Cozy getaway, 3 bedrooms 15 min from Cambridge
3 bedrooms, 3 queen beds, 1 bathroom
20–25 Sept
New place to stay
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Top guest favourite
Home in Cambridge
Sunset Breezes - quiet waterfront retreat
3 bedrooms, 5 beds, 2 bathrooms
12–17 Oct
4.99 out of 5 average rating, 227 reviews
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Guest favourite
Home in Cambridge
Chapman Farm Cottage
2 bedrooms, 3 beds, 1.5 bathrooms
22–27 Sept
5.0 out of 5 average rating, 5 reviews
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Superhost
Home in Woolford
Eastern Shore Waterfront-Pier, Kayaks, FirePit
2 bedrooms, 3 beds, 1 bathroom
5–10 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Cambridge
Chesapeake Sunset Cottage
2 bedrooms, 2 queen beds, 2 bathrooms
21–26 Sept
4.97 out of 5 average rating, 107 reviews
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Superhost
Home in Woolford
The Blue Heron-Spacious Waterfront house w/ kayaks
6 bedrooms, 10 beds, 4 bathrooms
11–16 Oct
4.67 out of 5 average rating, 58 reviews
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Superhost
Home in Cambridge
Drop Anchor on the Chesapeake
3 bedrooms, 5 beds, 2.5 bathrooms
21–26 Sept
4.86 out of 5 average rating, 7 reviews
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Home in Cambridge
280 Acre Waterfront Estate With Dock and Pool
5 bedrooms, 10 beds, 6 bathrooms
19–26 Sept
5.0 out of 5 average rating, 12 reviews
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Cottage in Cambridge
Cottage at Hudson Creek - Cozy Year-Round Retreat
3 bedrooms, 4 beds, 2 bathrooms
23–28 Sept