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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
6–11 Sept
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5.0 out of 5 average rating, 249 reviews
Superhost
Home in Woolford
The Blue Heron-Spacious Waterfront house w/ kayaks
6 bedrooms, 10 beds, 4 bathrooms
5–10 Oct
4.67 out of 5 average rating, 58 reviews
Top guest favourite
Home in Woolford
Waterfront Getaway with Dock
3 bedrooms, 4 beds, 2 bathrooms
25–30 Oct
4.94 out of 5 average rating, 190 reviews
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
Top guest favourite
Guest house in Woolford
Cozy Waterfront Garage Unit
1 bedroom, 2 beds, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 11 reviews
Home in Cambridge
Family and Pet-Friendly, Waterfront with Pier
4 bedrooms, 5 beds, 1.5 bathrooms
27 Sept – 2 Oct
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
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, 13 reviews
Top guest favourite
Tiny home in Cambridge
The Little House on the Farm, Water Access
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 244 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, 27 reviews
Guest favourite
Home in Church Creek
Waterview cottage on Chesapeake Bay
3 bedrooms, 6 beds, 1 bathroom
6–11 Sept
4.79 out of 5 average rating, 199 reviews
Top guest favourite
Home in Cambridge
Osprey's Retreat Waterfront w/ private beach/dock
3 bedrooms, 4 beds, 2.5 bathrooms
7–12 Sept
4.96 out of 5 average rating, 114 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, 53 reviews
Top guest favourite
Cabin in Lusby
Covenant Cove (Cove Point Beach)
2 bedrooms, 2 beds, 1.5 bathrooms
27 Sept – 2 Oct
4.87 out of 5 average rating, 103 reviews
Superhost
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, 4 reviews
Superhost
Home in Cambridge
Blackwater Bend | Waterfront Pool, Dock & Farm
4 bedrooms, 5 beds, 2.5 bathrooms
7–12 Sept
New place to stay
Top guest favourite
Cottage in Hollywood
Cottage on the Creek
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.99 out of 5 average rating, 106 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, 96 reviews
Guest favourite
Home in Cambridge
Choptank Riverside Retreat
3 bedrooms, 4 beds, 2 bathrooms
9–14 Sept
4.92 out of 5 average rating, 13 reviews