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Search results; Over 1,000 homes in Woolford

Top guest favourite
Cottage in Woolford
Bay Cottage w/ Pier-Kayaks near Cambridge
3 bedrooms, 8 beds, 2 private bathrooms
28 Sept – 3 Oct
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5.0 out of 5 average rating, 91 reviews
Top guest favourite
Home in Woolford
Newly Renovated Modern 3 bed 2 bath Water Front
3 bedrooms, 3 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 251 reviews
Guest favourite
Home in Woolford
Waterfront Getaway with Dock
3 bedrooms, 4 beds, 2 bathrooms
29 Oct – 3 Nov
4.93 out of 5 average rating, 195 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
Superhost
Home in Cambridge
Blackwater Bend | Private Pool & Riverfront
4 bedrooms, 5 beds, 2.5 bathrooms
20–25 Sept
New place to stay
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
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
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, 145 reviews
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
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
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
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
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
Top guest favourite
Flat in Church Creek
Nature's Rest in Church Creek
1 bedroom, 1 queen bed, 1 bathroom
25–30 Oct
4.97 out of 5 average rating, 452 reviews
Guest favourite
Cottage in Trappe
Private Waterfront Cottage with Pool and Poolhouse
2 bedrooms, 4 beds, 1 bathroom
3–8 Oct
4.85 out of 5 average rating, 47 reviews
Guest favourite
Home in Cambridge
Chapman Farm Cottage
2 bedrooms, 3 beds, 1.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 5 reviews
Home in Cambridge
Sunset on the Choptank River
4 bedrooms, 7 beds, 2.5 bathrooms
4–9 Oct
New place to stay
Top guest favourite
Home in Church Creek
Blackwater Sika & Wildlife Retreat
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 15 reviews
Guest favourite
Home in Cambridge
Chesapeake Sunset Retreat
4 bedrooms, 5 beds, 1.5 bathrooms
28 Oct – 2 Nov
4.84 out of 5 average rating, 38 reviews