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Search results; Over 1,000 homes in Madison

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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
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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
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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
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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
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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
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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
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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
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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, 227 reviews
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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
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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
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Home in Cambridge
Sunset on the Choptank River
4 bedrooms, 7 beds, 2.5 bathrooms
4–9 Oct
New place to stay
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Top guest favourite
Home in Woolford
Newly Renovated Modern 3 bed 2 bath Water Front
3 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 251 reviews
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Home in Cambridge
Amazing Everything!
4 bedrooms, 4 beds, 4.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 3 reviews
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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, 66 reviews
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Top guest favourite
Home in Cambridge
Gorgeous, Waterfront Home Is Perfect for Families!
7 bedrooms, 12 beds, 5 bathrooms
1–6 Oct
4.96 out of 5 average rating, 140 reviews
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Top guest favourite
Home in Dorchester County
Rippling Waters on Fishing Creek
3 bedrooms, 4 beds, 1.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 7 reviews
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Home in Cambridge
Sandy Point: a waterfront home on the cove
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
New place to stay
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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
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Superhost
Home in Woolford
Eastern Shore Waterfront-Pier, Kayaks, FirePit
2 bedrooms, 3 beds, 1 bathroom
28 Sept – 3 Oct
5.0 out of 5 average rating, 3 reviews