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Search results; Over 1,000 homes in Saint Michaels

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Top guest favourite
Cottage in St. Michaels
Cheerful 1-bedroom 1-bath cottage on quiet street
1 bedroom, 1 bed, 1.5 private bathrooms
10–15 Nov
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5.0 out of 5 average rating, 40 reviews
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Flat in St. Michaels
Blue Crab Lodge
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 159 reviews
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Home in St. Michaels
Miles Aweigh
3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
4.97 out of 5 average rating, 299 reviews
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Superhost
Home in St. Michaels
St. Michaels Waterfront Home with Pool
4 bedrooms, 5 beds, 4.5 bathrooms
1–6 Oct
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Home in St. Michaels
Ahoy St. Michaels! - A Historic Retreat
2 bedrooms, 3 beds, 2.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 59 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, 88 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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Home in Easton
4 bdrm, 3 bath, 2,700 sqft whole house on 1 acre
4 bedrooms, 4 beds, 3 bathrooms
1–6 Sept
4.97 out of 5 average rating, 99 reviews
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Home in Easton
St. Michaels Waterfront Home with Private Dock
3 bedrooms, 6 beds, 2.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 18 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, 173 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
7–12 Sept
4.99 out of 5 average rating, 124 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
4–9 Oct
4.97 out of 5 average rating, 301 reviews
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Home in St. Michaels
Grace Cottage, Saint Michaels Walk to everything!
2 bedrooms, 2 king beds, 2.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 15 reviews
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Home in Easton
Eastern Shore Retreat!
3 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 56 reviews
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Guest favourite
Home in Cambridge
The Oyster House
4 bedrooms, 7 beds, 3 bathrooms
7–12 Sept
4.9 out of 5 average rating, 77 reviews
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Home in Royal Oak
Waterfront Family Retreat - mins from St. Michaels
6 bedrooms, 9 beds, 4.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 5 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, 79 reviews
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Home in St. Michaels
Historic Berkeley Hall in the heart of town
2 bedrooms, 2 beds, 1.5 bathrooms
20–25 Sept
4.96 out of 5 average rating, 217 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
19–24 Sept
4.97 out of 5 average rating, 35 reviews