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Search results; Over 1,000 homes in Woolford

Top guest favorite
Home in Woolford
Starboard on McKeil Point, w/heated pool & hot tub
6 bedrooms, 11 beds, 4.5 private baths
Sep 5 – 10
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4.99 out of 5 average rating, 142 reviews
Top guest favorite
Home in Woolford
Newly Renovated Modern 3 bed 2 bath Water Front
3 bedrooms, 3 beds, 2 baths
Aug 19 – 24
5.0 out of 5 average rating, 249 reviews
Top guest favorite
Home in Woolford
Waterfront Getaway with Dock
3 bedrooms, 4 beds, 2 baths
Aug 23 – 28
4.94 out of 5 average rating, 189 reviews
Superhost
Home in Woolford
The Blue Heron-Spacious Waterfront house w/ kayaks
6 bedrooms, 10 beds, 4 baths
Aug 16 – 21
4.67 out of 5 average rating, 58 reviews
Top guest favorite
Apartment in Church Creek
Nature's Rest in Church Creek
1 bedroom, 1 queen bed, 1 bath
Aug 17 – 22
4.97 out of 5 average rating, 451 reviews
Top guest favorite
Home in Church Creek
Church Creek Charm (Close to Blackwater!)
3 bedrooms, 4 beds, 1 bath
Oct 12 – 17
4.96 out of 5 average rating, 167 reviews
Guest favorite
Home in Cambridge
Outline
3 bedrooms, 6 beds, 2 baths
Oct 30 – Nov 4
4.91 out of 5 average rating, 35 reviews
Top guest favorite
Guesthouse in Woolford
Cozy Waterfront Garage Unit
1 bedroom, 2 beds, 1 bath
Sep 29 – Oct 4
5.0 out of 5 average rating, 11 reviews
Guest favorite
Cottage in Trappe
Private Waterfront Cottage with Pool and Poolhouse
2 bedrooms, 4 beds, 1 bath
Sep 11 – 16
4.89 out of 5 average rating, 44 reviews
Top guest favorite
Farm stay in Madison
Madison Nature Getaway
1 bedroom, 2 beds, 1 bath
Aug 25 – 30
4.98 out of 5 average rating, 227 reviews
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Home in Cambridge
Relaxing Retreat on the Hudson
5 bedrooms, 5 beds, 2 baths
Aug 24 – 29
4.96 out of 5 average rating, 76 reviews
Top guest favorite
Cabin in Lusby
Covenant Cove (Cove Point Beach)
2 bedrooms, 2 beds, 1.5 baths
Sep 27 – Oct 2
4.87 out of 5 average rating, 101 reviews
Top guest favorite
Home in Taylors Island
Holliday House
3 bedrooms, 6 beds, 1.5 baths
Aug 14 – 19
5.0 out of 5 average rating, 23 reviews
Home in Cambridge
Sunset on the Choptank River
4 bedrooms, 7 beds, 2.5 baths
Aug 16 – 21
New place to stay
Top guest favorite
Home in Church Creek
House in Sika Deer & Snakehead Country
2 bedrooms, 6 beds, 1 bath
Aug 18 – 23
4.81 out of 5 average rating, 100 reviews
Top guest favorite
Home in Cambridge
Modern Chesapeake Waterfront - Heated Pool - Dock
5 bedrooms, 8 beds, 3.5 baths
Sep 20 – 25
5.0 out of 5 average rating, 10 reviews
Top guest favorite
Rooms in Nanticoke
A Piece of Paradise
2 bedrooms, 3 beds, 1 bath
Sep 7 – 12
4.97 out of 5 average rating, 225 reviews
Top guest favorite
Home in Bozman
The Cottage at Broad Creek
1 bedroom, 1 bed, 1.5 baths
Sep 11 – 16
5.0 out of 5 average rating, 48 reviews
Home in Cambridge
Family and Pet-Friendly, Waterfront with Pier
4 bedrooms, 5 beds, 1.5 baths
Sep 27 – Oct 2