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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, 5 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, 103 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
Home in Cambridge
Sunset on the Choptank River
4 bedrooms, 7 beds, 2.5 bathrooms
16–21 Aug
New place to stay
Home in Cambridge
Amazing Everything!
4 bedrooms, 4 beds, 4.5 bathrooms
11–16 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Cambridge
Relaxing Retreat on the Hudson
5 bedrooms, 5 beds, 2 bathrooms
24–29 Aug
4.96 out of 5 average rating, 76 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
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, 221 reviews
Holiday home in Cambridge
Very Private and Spacious Waterfront Family House
8 bedrooms, 15 beds, 6.5 bathrooms
15–22 Aug
4.76 out of 5 average rating, 68 reviews
Home in Cambridge
Waterfront Cambridge Retreat/View Choptank River
3 bedrooms, 3 beds, 3.5 bathrooms
12–17 Aug
New place to stay
Top guest favourite
Home in Woolford
Newly Renovated Modern 3 bed 2 bath Water Front
3 bedrooms, 3 beds, 2 bathrooms
11–16 Aug
5.0 out of 5 average rating, 248 reviews
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
Superhost
Home in Woolford
The Blue Heron-Spacious Waterfront house w/ kayaks
6 bedrooms, 10 beds, 4 bathrooms
16–21 Aug
4.67 out of 5 average rating, 58 reviews
Home in Cambridge
Family and Pet-Friendly, Waterfront with Pier
4 bedrooms, 5 beds, 1.5 bathrooms
27 Sept – 2 Oct
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
• Peaceful Point • A relaxing waterfront retreat
3 bedrooms, 7 beds, 2 bathrooms
28 Aug – 2 Sept
5.0 out of 5 average rating, 61 reviews