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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
Top guest favourite
Place to stay in Cambridge
Wye Three Oaks
2 bedrooms, 4 beds, 1 bathroom
9–14 Aug
4.96 out of 5 average rating, 102 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
Farm stay in Madison
Madison Nature Getaway
1 bedroom, 2 beds, 1 bathroom
25–30 Aug
4.98 out of 5 average rating, 227 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
Home in Madison
Madison Bay Retreat
2 bedrooms, 2 beds, 2 bathrooms
16–21 Aug
Top guest favourite
Tiny home in Cambridge
The Little House on the Farm, Water Access
1 bedroom, 1 queen bed, 1 bathroom
16–21 Aug
4.98 out of 5 average rating, 242 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, 188 reviews
Top guest favourite
Houseboat in Cambridge
Loveboat, Where Love Meets The Waves.
1 bedroom, 1 bed, 1 bathroom
17–22 Aug
5.0 out of 5 average rating, 18 reviews
Guest favourite
Home in Cambridge
Choptank Riverside Retreat
3 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
4.92 out of 5 average rating, 13 reviews
Top guest favourite
Flat in Cambridge
2nd floor studio apartment
1 bedroom, 2 beds, 1 bathroom
16–21 Aug
4.96 out of 5 average rating, 151 reviews
Guest favourite
Cottage in Wingate
Blue Crab Cottage: Remote+Nature+Fishing+Views
3 bedrooms, 5 beds, 1 bathroom
8–13 Aug
4.84 out of 5 average rating, 100 reviews
Guest favourite
Tiny home in Cambridge
Blackwater Tiny Cabin on Snakehead Creek
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.89 out of 5 average rating, 689 reviews
Top guest favourite
Room in Cambridge
Waterfront Room at Happy Campers
1 queen bed, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 64 reviews
Guest favourite
Room in Cambridge
Sailor's Retreat Pineapple Room
1 bed, 1 bathroom
11–16 Oct
5.0 out of 5 average rating, 14 reviews
Guest favourite
Home in Cambridge
Chesapeake Sunset Retreat
4 bedrooms, 5 beds, 1.5 bathrooms
8–13 Sept
4.83 out of 5 average rating, 36 reviews
Guest favourite
Campsite in Cambridge
Blackwater Snakehead Campsite/RV-Camper Parking
No bathroom
10–15 Aug
4.85 out of 5 average rating, 112 reviews
Home in Cambridge
Sunset on the Choptank River
4 bedrooms, 7 beds, 2.5 bathrooms
16–21 Aug
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