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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
,
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
Top guest favourite
Home in Cambridge
Serene getaway with great waterfront views!
3 bedrooms, 5 beds, 2.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 45 reviews
Top guest favourite
Home in Taylors Island
A Vacation for All, Away From It All
5 bedrooms, 13 beds, 5 bathrooms
20–25 Sept
4.96 out of 5 average rating, 51 reviews
Home in Cambridge
Waterfront, amazing views, pier, fishing/crabbing
3 bedrooms, 6 beds, 2 bathrooms
28 Sept – 3 Oct
4.83 out of 5 average rating, 64 reviews
Top guest favourite
Home in Cambridge
Chesapeake Sunset Cottage
2 bedrooms, 2 queen beds, 2 bathrooms
21–26 Sept
4.97 out of 5 average rating, 107 reviews
Home in Cambridge
280 Acre Waterfront Estate With Dock and Pool
5 bedrooms, 10 beds, 6 bathrooms
19–26 Sept
5.0 out of 5 average rating, 12 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
Flat in Cambridge
Lairds Cove
2 bedrooms, 2 beds, 1 bathroom
15–20 Sept
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
14–19 Sept
5.0 out of 5 average rating, 251 reviews
Home in Cambridge
Sunset on the Choptank River
4 bedrooms, 7 beds, 2.5 bathrooms
14–19 Sept
New place to stay
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
Top guest favourite
Home in Cambridge
• Peaceful Point • A relaxing waterfront retreat
3 bedrooms, 7 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 65 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
Top guest favourite
Home in Cambridge
Osprey's Retreat Waterfront w/ private beach/dock
3 bedrooms, 4 beds, 2.5 bathrooms
5–10 Oct
4.97 out of 5 average rating, 115 reviews
Home in Cambridge
Million Dollar Views
3 bedrooms, 2 queen beds, 2.5 bathrooms
20–25 Sept
New place to stay
Guest favourite
Home in Cambridge
Waterfront Oasis: SaltwaterPool&HotTub&PrivateDock
6 bedrooms, 11 beds, 3.5 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 30 reviews