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Search results; Over 1,000 homes in Woolford

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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 private bathrooms
5–10 Sept
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4.99 out of 5 average rating, 143 reviews
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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
6–11 Sept
5.0 out of 5 average rating, 249 reviews
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Guest favourite
Home in Woolford
Waterfront Getaway with Dock
3 bedrooms, 4 beds, 2 bathrooms
25–30 Oct
4.93 out of 5 average rating, 194 reviews
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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
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Guest favourite
Home in Madison
Bayfront Gem w/ Amazing Water Views + Pond!
4 bedrooms, 7 beds, 2.5 bathrooms
12–17 Oct
4.97 out of 5 average rating, 59 reviews
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Top guest favourite
Home in Cambridge
Chesapeake Sunset Cottage
2 bedrooms, 2 queen beds, 2 bathrooms
8–13 Sept
4.97 out of 5 average rating, 107 reviews
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Top guest favourite
Guest house in Woolford
Cozy Waterfront Garage Unit
1 bedroom, 2 beds, 1 bathroom
15–20 Nov
5.0 out of 5 average rating, 11 reviews
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Home in Cambridge
Family and Pet-Friendly, Waterfront with Pier
4 bedrooms, 5 beds, 1.5 bathrooms
27 Sept – 2 Oct
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Guest favourite
Home in Woolford
"Endless Summer" on the Chesapeake!
4 bedrooms, 7 beds, 2.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 6 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
8–13 Sept
4.96 out of 5 average rating, 51 reviews
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Top guest favourite
Flat in Church Creek
Nature's Rest in Church Creek
1 bedroom, 1 queen bed, 1 bathroom
28 Sept – 3 Oct
4.97 out of 5 average rating, 452 reviews
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Guest favourite
Home in Cambridge
Lovely home away from home
3 bedrooms, 4 beds, 1.5 bathrooms
27 Sept – 2 Oct
4.93 out of 5 average rating, 28 reviews
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Top guest favourite
Home in Cambridge
Serene getaway with great waterfront views!
3 bedrooms, 5 beds, 2.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 45 reviews
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Top guest favourite
Guest house in Cambridge
Rosses Chance Guest House
1 bedroom, 2 beds, 1 bathroom
22–27 Sept
4.99 out of 5 average rating, 144 reviews
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Guest favourite
Home in Fishing Creek
Chesapeake Bay Retreat
3 bedrooms, 4 beds, 2.5 bathrooms
7–12 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
8–13 Sept
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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
7–12 Sept
4.97 out of 5 average rating, 115 reviews
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Home in Cambridge
Amazing Everything!
4 bedrooms, 4 beds, 4.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Dorchester County
Rippling Waters on Fishing Creek
3 bedrooms, 4 beds, 1.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 6 reviews