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Search results; Over 1,000 homes in Woolford

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Guest favourite
Home in Woolford
Waterfront Getaway with Dock
3 bedrooms, 4 beds, 2 private bathrooms
29 Oct – 3 Nov
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4.93 out of 5 average rating, 196 reviews
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Top guest favourite
Home in Woolford
Newly Renovated Modern 3 bed 2 bath Water Front
3 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 251 reviews
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Superhost
Home in Woolford
The Blue Heron-Spacious Waterfront house w/ kayaks
6 bedrooms, 10 beds, 4 bathrooms
11–16 Oct
4.64 out of 5 average rating, 59 reviews
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Home in Madison
Cozy getaway, 3 bedrooms 15 min from Cambridge
3 bedrooms, 3 queen beds, 1 bathroom
4–9 Oct
New place to stay
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Guest favourite
Home in Woolford
Gorgeous Waterfront, Beach, Pool, Pets- 7 Bd /5ba
7 bedrooms, 13 beds, 5 bathrooms
12–17 Oct
4.98 out of 5 average rating, 91 reviews
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Home in Cambridge
Waterfront Retreat | 3BR Near Ironman Maryland
3 bedrooms, 3 beds, 3 bathrooms
30 Oct – 4 Nov
New place to stay
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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
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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
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Superhost
Home in Cambridge
Blackwater Bend | Private Pool & Riverfront
4 bedrooms, 5 beds, 2.5 bathrooms
1–6 Oct
New place to stay
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Home in Cambridge
More, than just a place to sleep - welcome home!
3 bedrooms, 3 beds, 2 bathrooms
5–10 Oct
New place to stay
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Guest favourite
Home in Cambridge
Choptank Riverside Retreat
3 bedrooms, 4 beds, 2 bathrooms
1–6 Oct
4.93 out of 5 average rating, 15 reviews
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Top guest favourite
Home in Taylors Island
About Time Waterfront Views | Dock | Sleeps 15
5 bedrooms, 13 beds, 2.5 bathrooms
19–24 Oct
5.0 out of 5 average rating, 22 reviews
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Top guest favourite
Home in Woolford
Starboard on McKeil Point, w/heated pool & hot tub
6 bedrooms, 11 beds, 4.5 bathrooms
1–6 Oct
4.99 out of 5 average rating, 144 reviews
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Flat in Cambridge
Lairds Cove
2 bedrooms, 2 beds, 1 bathroom
1–6 Oct
New place to stay
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Guest favourite
Home in Cambridge
Waterfront Oasis: SaltwaterPool&HotTub&PrivateDock
6 bedrooms, 11 beds, 3.5 bathrooms
5–10 Oct
5.0 out of 5 average rating, 31 reviews
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Superhost
Home in Woolford
Eastern Shore Waterfront-Pier, Kayaks, FirePit
2 bedrooms, 3 beds, 1 bathroom
21–26 Oct
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Place to stay in Cambridge
Wye Three Oaks
2 bedrooms, 4 beds, 1 bathroom
7–12 Oct
4.95 out of 5 average rating, 111 reviews
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Top guest favourite
Home in Cambridge
Chesapeake Sunset Cottage
2 bedrooms, 2 queen beds, 2 bathrooms
1–6 Oct
4.97 out of 5 average rating, 107 reviews
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Home in Cambridge
Sunset on the Choptank River
4 bedrooms, 7 beds, 2.5 bathrooms
4–9 Oct
New place to stay