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Search results; Over 1,000 homes in Woolford

Guest favourite
Home in Woolford
"Endless Summer" on the Chesapeake!
4 bedrooms, 7 beds, 2.5 private bathrooms
21–26 Sept
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5.0 out of 5 average rating, 8 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
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
Home in Cambridge
Waterfront Retreat | 3BR Near Ironman Maryland
3 bedrooms, 3 beds, 3 bathrooms
17–22 Sept
New place to stay
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, 144 reviews
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
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
Guest favourite
Home in Cambridge
Waterfront Oasis: SaltwaterPool&HotTub&PrivateDock
6 bedrooms, 11 beds, 3.5 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 31 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
Home in Cambridge
Sunset on the Choptank River
4 bedrooms, 7 beds, 2.5 bathrooms
4–9 Oct
New place to stay
Flat in Cambridge
Lairds Cove
2 bedrooms, 2 beds, 1 bathroom
15–20 Sept
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
Great Historic Cambridge Home With Parking!
4 bedrooms, 7 beds, 3.5 bathrooms
20–25 Sept
4.95 out of 5 average rating, 286 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, 30 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
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 Church Creek
Church Creek Charm (Close to Blackwater!)
3 bedrooms, 4 beds, 1 bathroom
26–31 Oct
4.96 out of 5 average rating, 170 reviews
Top guest favourite
Farm stay in Madison
Madison Nature Getaway
1 bedroom, 2 beds, 1 bathroom
9–14 Nov
4.98 out of 5 average rating, 228 reviews