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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
29 Aug – 3 Sept
4.98 out of 5 average rating, 87 reviews
Guest favourite
Home in Woolford
"Endless Summer" on the Chesapeake!
4 bedrooms, 7 beds
17–22 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Place to stay in Cambridge
Wye Three Oaks
2 bedrooms, 4 beds
9–14 Aug
4.96 out of 5 average rating, 102 reviews
Home in Cambridge
Sunset on the Choptank River
4 bedrooms, 7 beds
16–21 Aug
New place to stay
Top guest favourite
Home in Woolford
Waterfront Getaway with Dock
3 bedrooms, 4 beds
23–28 Aug
4.94 out of 5 average rating, 188 reviews
Top guest favourite
Houseboat in Cambridge
Loveboat, Where Love Meets The Waves.
1 bedroom, 1 bed
16–21 Aug
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Home in Cambridge
Serene getaway with great waterfront views!
3 bedrooms, 5 beds
10–15 Aug
5.0 out of 5 average rating, 43 reviews
Top guest favourite
Home in Cambridge
Relaxing Retreat on the Hudson
5 bedrooms, 5 beds
24–29 Aug
4.96 out of 5 average rating, 74 reviews
Top guest favourite
Tiny home in Cambridge
The Little House on the Farm, Water Access
1 bedroom, 1 queen bed
16–21 Aug
4.98 out of 5 average rating, 242 reviews
Top guest favourite
Farm stay in Madison
Madison Nature Getaway
1 bedroom, 2 beds
25–30 Aug
4.98 out of 5 average rating, 227 reviews
Superhost
Home in Cambridge
Drop Anchor on the Chesapeake
3 bedrooms, 5 beds
17–22 Aug
4.86 out of 5 average rating, 7 reviews
Top guest favourite
Room in Cambridge
Stevens’ Gift, Bay Window with riverview.
2 beds
17–22 Aug
4.96 out of 5 average rating, 48 reviews
Guest favourite
Home in Cambridge
Modern Chesapeake Waterfront - Heated Pool - Dock
5 bedrooms, 8 beds
20–25 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Cambridge
Chesapeake Sunset Cottage
2 bedrooms, 2 queen beds
31 Aug – 5 Sept
4.97 out of 5 average rating, 106 reviews
Top guest favourite
Flat in Cambridge
2nd floor studio apartment
1 bedroom, 2 beds
16–21 Aug
4.96 out of 5 average rating, 150 reviews
Guest favourite
Home in Cambridge
Waterfront Cambridge Home: Pool & Dock!
4 bedrooms, 7 beds
23–28 Aug
4.87 out of 5 average rating, 15 reviews
Top guest favourite
Home in Woolford
Starboard on McKeil Point, w/heated pool & hot tub
6 bedrooms, 11 beds
5–10 Sept
4.99 out of 5 average rating, 142 reviews
Guest favourite
Home in Cambridge
Chesapeake Sunset Retreat
4 bedrooms, 5 beds
8–13 Sept
4.83 out of 5 average rating, 36 reviews