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Search results; Over 1,000 homes in Taylors Island

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Top guest favourite
Home in Taylors Island
A Vacation for All, Away From It All
5 bedrooms, 13 beds, 5 private bathrooms
20–25 Sept
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4.96 out of 5 average rating, 51 reviews
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Top guest favourite
Home in Taylors Island
Holliday House
3 bedrooms, 6 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 25 reviews
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Top guest favourite
Home in Taylors Island
About Time Waterfront Views | Dock | Sleeps 15
5 bedrooms, 13 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 22 reviews
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Home in Taylors Island
Taylors Island Bunkhouse
1 bedroom, 4 beds
20–25 Sept
4.86 out of 5 average rating, 7 reviews
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Home in Taylors Island
About Time-Bunkhouse Only
2 bedrooms, 6 single beds
8–13 Nov
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Guest favourite
Home in Cambridge
Chesapeake Bay Retreat
6 bedrooms, 14 beds
20–25 Sept
5.0 out of 5 average rating, 17 reviews
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Flat in Cambridge
Lairds Cove
2 bedrooms, 2 beds
15–20 Sept
New place to stay
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Top guest favourite
Home in Cambridge
Sunset Breezes - quiet waterfront retreat
3 bedrooms, 5 beds
12–17 Oct
4.99 out of 5 average rating, 227 reviews
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Superhost
Home in Taylors Island
Waterside Sunset On The Creek
3 bedrooms, 5 beds
20–25 Sept
4.64 out of 5 average rating, 25 reviews
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Guest favourite
Home in Cambridge
Choptank Riverside Retreat
3 bedrooms, 4 beds
21–26 Sept
4.93 out of 5 average rating, 15 reviews
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Guest favourite
Home in Lusby
Down the Country
4 bedrooms, 8 beds
28 Sept – 3 Oct
4.92 out of 5 average rating, 24 reviews
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Top guest favourite
Home in Madison
Bayfront Gem w/ Amazing Water Views + Pond!
4 bedrooms, 7 beds
12–17 Oct
4.97 out of 5 average rating, 61 reviews
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Guest favourite
Home in Lusby
Spacious Lakefront Cottage w/ Private Pier
5 bedrooms, 15 beds
12–17 Oct
4.85 out of 5 average rating, 86 reviews
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Home in Cambridge
Family and Pet-Friendly, Waterfront with Pier
4 bedrooms, 5 beds
27 Sept – 2 Oct
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Top guest favourite
Guest suite in Lusby
Waterfront on St. Leonard Creek at Fort Hill
2 bedrooms, 4 beds
27 Oct – 1 Nov
4.98 out of 5 average rating, 119 reviews
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Guest favourite
Home in Fishing Creek
'The Bayside Escape' Remote Chesapeake Bay Estate
6 bedrooms, 14 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Home in Church Creek
Blackwater Sika & Wildlife Retreat
3 bedrooms, 4 beds
20–25 Sept
5.0 out of 5 average rating, 15 reviews
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Top guest favourite
Home in Cambridge
Gorgeous, Waterfront Home Is Perfect for Families!
7 bedrooms, 12 beds
1–6 Oct
4.96 out of 5 average rating, 140 reviews
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Superhost
Home in Fishing Creek
Hoopers Landing | Private Dock | Hot Tub
3 bedrooms, 5 beds
26 Sept – 1 Oct
New place to stay