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Search results; Over 1,000 homes in Madison

Top guest favourite
Home in Madison
Madison Bay Club House
3 bedrooms, 7 beds, 2.5 shared bathrooms
29 Aug – 3 Sept
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5.0 out of 5 average rating, 52 reviews
Guest favourite
Home in Woolford
Gorgeous Waterfront, Beach, Pool, Pets- 7 Bd /5ba
7 bedrooms, 13 beds, 5 bathrooms
29 Aug – 3 Sept
4.98 out of 5 average rating, 87 reviews
Top guest favourite
Home in Woolford
Starboard on McKeil Point, w/heated pool & hot tub
6 bedrooms, 11 beds, 4.5 bathrooms
5–10 Sept
4.99 out of 5 average rating, 142 reviews
Guest favourite
Home in Woolford
"Endless Summer" on the Chesapeake!
4 bedrooms, 7 beds, 2.5 bathrooms
17–22 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Place to stay in Cambridge
Wye Three Oaks
2 bedrooms, 4 beds, 1 bathroom
7–12 Sept
4.96 out of 5 average rating, 104 reviews
Top guest favourite
Home in Woolford
Newly Renovated Modern 3 bed 2 bath Water Front
3 bedrooms, 3 beds, 2 bathrooms
19–24 Aug
5.0 out of 5 average rating, 249 reviews
Top guest favourite
Home in Woolford
Waterfront Getaway with Dock
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.94 out of 5 average rating, 189 reviews
Guest favourite
Home in Cambridge
The Sailor’s Shanty
2 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Cambridge
Sunset Breezes - quiet waterfront retreat
3 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
4.99 out of 5 average rating, 222 reviews
Top guest favourite
Home in Cambridge
Serene getaway with great waterfront views!
3 bedrooms, 5 beds, 2.5 bathrooms
17–22 Aug
5.0 out of 5 average rating, 43 reviews
Top guest favourite
Farm stay in Madison
Madison Nature Getaway
1 bedroom, 2 beds, 1 bathroom
25–30 Aug
4.98 out of 5 average rating, 227 reviews
Home in Cambridge
Amazing Everything!
4 bedrooms, 4 beds, 4.5 bathrooms
14–19 Aug
5.0 out of 5 average rating, 3 reviews
Home in Cambridge
Sunset on the Choptank River
4 bedrooms, 7 beds, 2.5 bathrooms
16–21 Aug
New place to stay
Superhost
Home in Cambridge
Drop Anchor on the Chesapeake
3 bedrooms, 5 beds, 2.5 bathrooms
17–22 Aug
4.86 out of 5 average rating, 7 reviews
Top guest favourite
Guest house in Cambridge
The Loft at Sailor's Retreat. Waterfront Apartment
1 bedroom, 1 king bed, 1 bathroom
7–12 Sept
4.99 out of 5 average rating, 117 reviews
Top guest favourite
Guest house in Cambridge
Rosses Chance Guest House
1 bedroom, 2 beds, 1 bathroom
22–27 Sept
4.99 out of 5 average rating, 143 reviews
Guest favourite
Home in Cambridge
Chesapeake Bay Retreat
6 bedrooms, 14 beds, 3 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 14 reviews
Home in Cambridge
Family and Pet-Friendly, Waterfront with Pier
4 bedrooms, 5 beds, 1.5 bathrooms
27 Sept – 2 Oct
Home in Cambridge
280 Acre Waterfront Estate With Dock and Pool
5 bedrooms, 10 beds, 6 bathrooms
15–22 Aug
5.0 out of 5 average rating, 11 reviews