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Search results; Over 1,000 homes in Woolford

Top guest favourite
Home in Woolford
Newly Renovated Modern 3 bed 2 bath Water Front
3 bedrooms, 3 beds, 2 private bathrooms
21–26 Sept
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5.0 out of 5 average rating, 250 reviews
Top guest favourite
Flat in Church Creek
Nature's Rest in Church Creek
1 bedroom, 1 queen bed, 1 bathroom
22–27 Sept
4.97 out of 5 average rating, 452 reviews
Featured hotel
Room in St. Michaels
Standard queen room
1 queen bed, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 3 reviews
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
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
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
Top 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, 60 reviews
Holiday home in Cambridge
Very Private and Spacious Waterfront Family House
8 bedrooms, 15 beds, 6.5 bathrooms
7–12 Sept
4.76 out of 5 average rating, 68 reviews
Guest favourite
Room in Cambridge
Stevens’ Gift, Grandfather’s room
1 double bed, 2 bathrooms
8–13 Sept
4.94 out of 5 average rating, 50 reviews
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
Top guest favourite
Room in Cambridge
Sailor's Retreat Captain's Quarters
1 king bed, 1 bathroom
1–6 Oct
4.98 out of 5 average rating, 97 reviews
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
Superhost
Home in Woolford
Eastern Shore Waterfront-Pier, Kayaks, FirePit
2 bedrooms, 3 beds, 1 bathroom
8–13 Sept
Guest favourite
Home in Cambridge
The Sailor’s Shanty
2 bedrooms, 3 beds, 2 bathrooms
12–17 Sept
5.0 out of 5 average rating, 16 reviews
Home in Cambridge
Sunset on the Choptank River
4 bedrooms, 5 beds, 2.5 bathrooms
7–12 Sept
New place to stay
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
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
Guest favourite
Home in Cambridge
Chesapeake Sunset Retreat
4 bedrooms, 5 beds, 1.5 bathrooms
8–13 Sept
4.84 out of 5 average rating, 38 reviews
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