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Search results; Over 1,000 homes in Woolford

Guest favourite
Home in Woolford
Waterfront Getaway with Dock
3 bedrooms, 4 beds, 2 private bathrooms
29 Oct – 3 Nov
,
4.93 out of 5 average rating, 194 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
Top guest favourite
Home in Woolford
Newly Renovated Modern 3 bed 2 bath Water Front
3 bedrooms, 3 beds, 2 bathrooms
11–16 Sept
5.0 out of 5 average rating, 251 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
Home in Cambridge
Million Dollar Views
3 bedrooms, 3 beds, 2.5 bathrooms
11–16 Sept
New place to stay
Holiday home in Cambridge
Very Private and Spacious Waterfront Family House
8 bedrooms, 15 beds, 6.5 bathrooms
27 Sept – 2 Oct
4.77 out of 5 average rating, 69 reviews
Superhost
Home in Woolford
Eastern Shore Waterfront-Pier, Kayaks, FirePit
2 bedrooms, 3 beds, 1 bathroom
28 Sept – 3 Oct
Superhost
Home in Cambridge
Blackwater Bend | Waterfront Pool, Dock & Farm
4 bedrooms, 5 beds, 2.5 bathrooms
13–18 Sept
New place to stay
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
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
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, 143 reviews
Top guest favourite
Home in Church Creek
Blackwater Sika & Wildlife Retreat
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 14 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
Home in Cambridge
Sunset on the Choptank River
4 bedrooms, 7 beds, 2.5 bathrooms
11–16 Sept
New place to stay
Top guest favourite
Home in Cambridge
Chesapeake Sunset Cottage
2 bedrooms, 2 queen beds, 2 bathrooms
11–16 Sept
4.97 out of 5 average rating, 107 reviews
Superhost
Home in Fishing Creek
Hoopers Landing | Private Dock | Hot Tub
3 bedrooms, 5 beds, 4 bathrooms
26 Sept – 1 Oct
New place to stay
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, 30 reviews
Guest favourite
Home in Woolford
"Endless Summer" on the Chesapeake!
4 bedrooms, 7 beds, 2.5 bathrooms
11–16 Sept
5.0 out of 5 average rating, 8 reviews
Superhost
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, 46 reviews