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Search results; Over 1,000 homes in Madison

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
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
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, 89 reviews
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
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
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
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, 226 reviews
Home in Cambridge
Family and Pet-Friendly, Waterfront with Pier
4 bedrooms, 5 beds, 1.5 bathrooms
27 Sept – 2 Oct
Flat in Cambridge
Lairds Cove
2 bedrooms, 2 beds, 1 bathroom
15–20 Sept
New place to stay
Top guest favourite
Home in Taylors Island
About Time Waterfront Views | Dock | Sleeps 15
5 bedrooms, 13 beds, 2.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 22 reviews
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
Home in Cambridge
Waterfront Retreat | 3BR Near Ironman Maryland
3 bedrooms, 3 beds, 3 bathrooms
17–22 Sept
New place to stay
Top guest favourite
Home in Cambridge
Relaxing Retreat on the Hudson
5 bedrooms, 5 beds, 2 bathrooms
4–9 Oct
4.96 out of 5 average rating, 80 reviews
Guest favourite
Home in Cambridge
Chesapeake Bay Retreat
6 bedrooms, 14 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 17 reviews
Guest favourite
Home in Cambridge
Chesapeake Sunset Retreat
4 bedrooms, 5 beds, 1.5 bathrooms
28 Oct – 2 Nov
4.84 out of 5 average rating, 38 reviews
Top guest favourite
Home in Taylors Island
A Vacation for All, Away From It All
5 bedrooms, 13 beds, 5 bathrooms
13–18 Sept
4.96 out of 5 average rating, 51 reviews
Holiday home in Cambridge
Very Private and Spacious Waterfront Family House
8 bedrooms, 15 beds, 6.5 bathrooms
27 Sept – 2 Oct
4.77 out of 5 average rating, 69 reviews
Home in Cambridge
Amazing Everything!
4 bedrooms, 4 beds, 4.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Place to stay in Cambridge
Wye Three Oaks
2 bedrooms, 4 beds, 1 bathroom
4–9 Oct
4.95 out of 5 average rating, 110 reviews