filters

Search results; Over 1,000 homes in Madison

Photo 1 of 29
Top guest favourite
Farm stay in Madison
Madison Nature Getaway
1 bedroom, 2 beds, 1 private bathroom
9–14 Nov
,
4.98 out of 5 average rating, 228 reviews
Photo 1 of 29
Top guest favourite
Home in Woolford
Gorgeous Waterfront, Beach, Pool, Pets- 7 Bd /5ba
7 bedrooms, 13 beds
21–26 Sept
4.98 out of 5 average rating, 90 reviews
Photo 1 of 29
Top guest favourite
Home in Woolford
Starboard on McKeil Point, w/heated pool & hot tub
6 bedrooms, 11 beds
28 Sept – 3 Oct
4.99 out of 5 average rating, 144 reviews
Photo 1 of 29
Top guest favourite
Home in Madison
Madison Bay Club House
3 bedrooms, 7 beds
20–25 Sept
5.0 out of 5 average rating, 54 reviews
Photo 1 of 29
Guest favourite
Home in Woolford
"Endless Summer" on the Chesapeake!
4 bedrooms, 7 beds
21–26 Sept
5.0 out of 5 average rating, 8 reviews
Photo 1 of 29
Home in Cambridge
Amazing Everything!
4 bedrooms, 4 beds
21–26 Sept
5.0 out of 5 average rating, 3 reviews
Photo 1 of 28
Home in Cambridge
Family and Pet-Friendly, Waterfront with Pier
4 bedrooms, 5 beds
27 Sept – 2 Oct
Photo 1 of 17
Flat in Cambridge
Lairds Cove
2 bedrooms, 2 beds
20–25 Sept
New place to stay
Photo 1 of 29
Home in Madison
Madison Bay Retreat
2 bedrooms, 2 beds
22–27 Sept
Photo 1 of 17
Guest favourite
Place to stay in Cambridge
Wye Three Oaks
2 bedrooms, 4 beds
25–30 Sept
4.95 out of 5 average rating, 110 reviews
Photo 1 of 12
Home in Madison
Cozy getaway, 3 bedrooms 15 min from Cambridge
3 bedrooms, 3 queen beds
20–25 Sept
New place to stay
Photo 1 of 29
Top guest favourite
Home in Cambridge
Sunset Breezes - quiet waterfront retreat
3 bedrooms, 5 beds
12–17 Oct
4.99 out of 5 average rating, 227 reviews
Photo 1 of 15
Guest favourite
Home in Cambridge
Chapman Farm Cottage
2 bedrooms, 3 beds
22–27 Sept
5.0 out of 5 average rating, 5 reviews
Photo 1 of 29
Superhost
Home in Woolford
Eastern Shore Waterfront-Pier, Kayaks, FirePit
2 bedrooms, 3 beds
5–10 Oct
5.0 out of 5 average rating, 3 reviews
Photo 1 of 29
Top guest favourite
Home in Cambridge
Chesapeake Sunset Cottage
2 bedrooms, 2 queen beds
21–26 Sept
4.97 out of 5 average rating, 107 reviews
Photo 1 of 29
Superhost
Home in Woolford
The Blue Heron-Spacious Waterfront house w/ kayaks
6 bedrooms, 10 beds
11–16 Oct
4.67 out of 5 average rating, 58 reviews
Photo 1 of 29
Home in Cambridge
280 Acre Waterfront Estate With Dock and Pool
5 bedrooms, 10 beds
19–26 Sept
5.0 out of 5 average rating, 12 reviews
Photo 1 of 29
Top guest favourite
Home in Taylors Island
A Vacation for All, Away From It All
5 bedrooms, 13 beds
20–25 Sept
4.96 out of 5 average rating, 51 reviews
Photo 1 of 29
Top guest favourite
Home in Cambridge
Relaxing Retreat on the Hudson
5 bedrooms, 5 beds
4–9 Oct
4.96 out of 5 average rating, 81 reviews