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Search results; Over 1,000 homes in Tilghman Island

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Top guest favourite
Home in Tilghman Island
Panoramic water views
2 bedrooms, 2 beds, 1 private bathroom
25–30 Oct
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4.95 out of 5 average rating, 43 reviews
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Top guest favourite
Home in Tilghman Island
The Getaway
3 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 34 reviews
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Guest favourite
Home in Tilghman Island
Charming Tilghman Island Cottage | Pets Welcome
3 bedrooms, 4 beds, 2.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 39 reviews
Photo 1 of 29
Guest favourite
Home in Tilghman Island
Tranquility on Tilghman Island – Wide Water Views
5 bedrooms, 8 beds, 4.5 bathrooms
12–17 Oct
4.96 out of 5 average rating, 46 reviews
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Guest favourite
Home in Tilghman Island
Pet-Friendly Summer Retreat on Tilghman
3 bedrooms, 4 beds, 2 bathrooms
22–27 Sept
4.81 out of 5 average rating, 16 reviews
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Guest favourite
Home in Tilghman Island
Tilghman Island Retreat By Knapps Narrows!
2 bedrooms, 3 beds, 2 bathrooms
5–10 Oct
4.95 out of 5 average rating, 22 reviews
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Superhost
Home in Tilghman Island
Bayfront Escape Tilghman Island | Sunset Views
3 bedrooms, 3 queen beds, 2 bathrooms
25–30 Oct
4.84 out of 5 average rating, 19 reviews
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Superhost
Home in Tilghman Island
Waterfront Bliss | an ESVR property
4 bedrooms, 6 beds, 3 bathrooms
20–25 Sept
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Top guest favourite
Guest suite in Tilghman Island
Black Walnut Cove Retreat, Tilghman Island
1 bedroom, 4 beds, 1 bathroom
27 Sept – 2 Oct
4.97 out of 5 average rating, 181 reviews
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Home in Tilghman Island
Sunsets on Skipjack
3 bedrooms, 3 queen beds, 2 bathrooms
23–28 Sept
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Guest favourite
Home in Tilghman Island
Tilghman Retreat: A house on the Chesapeake Bay.
3 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
4.94 out of 5 average rating, 54 reviews
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Guest favourite
Home in Sherwood
Chesapeake Mansion-heated pool 30acre waterfront
8 bedrooms, 11 beds, 11 bathrooms
5–10 Oct
4.99 out of 5 average rating, 81 reviews
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Guest favourite
Home in Tilghman Island
Tilghman Island Cottage – Pets Welcome!
3 bedrooms, 3 beds, 2 bathrooms
3–8 Oct
4.88 out of 5 average rating, 17 reviews
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Superhost
Home in Tilghman Island
Charming 2 Bedroom Cottage on Tilghman Island
2 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
4.73 out of 5 average rating, 15 reviews
Photo 1 of 29
Top guest favourite
Home in Sherwood
Time Stands Still, While Memories Are Made.
6 bedrooms, 8 beds, 4.5 bathrooms
4–9 Oct
4.97 out of 5 average rating, 35 reviews
Photo 1 of 29
Guest favourite
Home in Shady Side
Waterfront Coastal Retreat w/ Beach Access
3 bedrooms, 1 bathroom
28 Sept – 3 Oct
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
Home in St. Michaels
Private&Cozy/3br+2ba/1mi to town
3 bedrooms, 3 beds, 2 bathrooms
25–30 Oct
4.94 out of 5 average rating, 89 reviews
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Guest favourite
Home in Sherwood
Punch Point boasts a sandy beach w/ pool and pier
5 bedrooms, 5 beds, 4.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 24 reviews
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Guest favourite
Home in Sherwood
Paradise Found - Duck Duck Goose on Waterhole Cove
7 bedrooms, 8 beds, 7 bathrooms
29 Sept – 4 Oct
5.0 out of 5 average rating, 7 reviews