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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
18–23 Oct
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4.98 out of 5 average rating, 54 reviews
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Featured hotel
Hotel in St. Michaels
St. Michaels Inn, Standard double room
1 bedroom, 2 double beds, 1 bathroom
4–9 Oct
New place to stay
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Top guest favourite
Flat in St. Michaels
Blue Crab Lodge
2 bedrooms, 3 beds, 1 bathroom
18–23 Oct
4.98 out of 5 average rating, 162 reviews
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Guest favourite
Flat in St. Michaels
Downtown St. Michaels | Porch + Pet-Friendly
3 bedrooms, 4 beds, 2 bathrooms
11–16 Oct
4.96 out of 5 average rating, 25 reviews
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Top guest favourite
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
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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Top guest favourite
Home in St. Michaels
Grace Cottage, Saint Michaels Walk to everything!
2 bedrooms, 2 king beds, 2.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 17 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 St. Michaels
St. Michaels Waterfront Retreat | Pet Friendly
3 bedrooms, 4 beds, 3.5 bathrooms
1–6 Oct
4.87 out of 5 average rating, 23 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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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
Houseboat in Cambridge
Loveboat, Where Love Meets The Waves.
1 bedroom, 1 bed, 1 bathroom
25–30 Oct
4.9 out of 5 average rating, 31 reviews
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Top guest favourite
Home in Easton
Eastern Shore Retreat!
3 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 58 reviews
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Top guest favourite
Home in Bozman
The Cottage at Broad Creek
1 bedroom, 1 bed, 1.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 54 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
1–6 Oct
5.0 out of 5 average rating, 26 reviews
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Top guest favourite
Cottage in St. Michaels
La Casita on Harris Creek, St. Michaels
1 bedroom, 2 beds, 1 bathroom
1–6 Oct
4.98 out of 5 average rating, 204 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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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, 232 reviews
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Home in Easton
Royal Oak Roadhouse
3 bedrooms, 3 beds, 2.5 bathrooms
1–6 Oct