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Search results; Over 1,000 homes in Saint Michaels

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Top guest favourite
Home in St. Michaels
Margaret Wells House
2 bedrooms, 2 beds, 2 private bathrooms
27 Sept – 2 Oct
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4.98 out of 5 average rating, 54 reviews
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Flat in St. Michaels
Blue Crab Lodge
2 bedrooms, 3 beds, 1 bathroom
18–23 Oct
4.98 out of 5 average rating, 161 reviews
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Home in St. Michaels
Shipwrights Cottage in Town!
2 bedrooms, 3 beds, 2 bathrooms
11–16 Oct
4.99 out of 5 average rating, 177 reviews
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Top guest favourite
Cottage in St. Michaels
Lovely Waterfront Cottage on 2 acres, St. Michaels
3 bedrooms, 5 beds, 2 bathrooms
4–9 Oct
4.97 out of 5 average rating, 35 reviews
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Home in Easton
Newly Renovated Modern Waterfront Home
5 bedrooms, 13 beds, 5.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 46 reviews
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Guest favourite
Flat in St. Michaels
Downtown St. Michaels | Porch + Pet-Friendly
3 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 25 reviews
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Top guest favourite
Home in St. Michaels
Ahoy St. Michaels! - A Historic Retreat
2 bedrooms, 3 beds, 2.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 65 reviews
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Guest favourite
Home in St. Michaels
Summer Retreat — Pool, Hot Tub & Outdoor Oasis
3 bedrooms, 4 beds, 3.5 bathrooms
24–29 Sept
4.86 out of 5 average rating, 22 reviews
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Home in St. Michaels
Historic Berkeley Hall in the heart of town
2 bedrooms, 2 beds, 1.5 bathrooms
25–30 Oct
4.96 out of 5 average rating, 220 reviews
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Guest favourite
Home in Wittman
Sewell Point Bungalow
3 bedrooms, 4 beds, 1 bathroom
4–9 Oct
4.94 out of 5 average rating, 17 reviews
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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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Top guest favourite
Home in St. Michaels
Cozy, Family-Friendly Log Cabin-St. Michaels
4 bedrooms, 5 beds, 3 bathrooms
4–9 Oct
5.0 out of 5 average rating, 19 reviews
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Top guest favourite
Home in St. Michaels
Dr. Miller house. Best location-in the heart town
2 bedrooms, 3 beds, 1.5 bathrooms
4–9 Oct
4.92 out of 5 average rating, 231 reviews
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Top guest favourite
Cottage in St. Michaels
The Little Anchor Cottage, St. Michaels, MD
2 bedrooms, 3 beds, 1 bathroom
18–23 Oct
4.97 out of 5 average rating, 303 reviews
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Home in Easton
Arcadia Shores On The Cove
4 bedrooms, 7 beds, 4 bathrooms
21–26 Sept
4.95 out of 5 average rating, 21 reviews
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Cottage in St. Michaels
La Casita on Harris Creek, St. Michaels
1 bedroom, 2 beds, 1 bathroom
29 Sept – 4 Oct
4.98 out of 5 average rating, 203 reviews
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Guest favourite
Cabin in St. Michaels
True St. Michaels 6 Acre Waterfront w/heated pool
5 bedrooms, 11 beds, 3 bathrooms
4–9 Oct
4.99 out of 5 average rating, 127 reviews
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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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Home in Tilghman Island
Panoramic water views
2 bedrooms, 2 queen beds, 1 bathroom
25–30 Oct
4.95 out of 5 average rating, 43 reviews