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Search results; Over 1,000 homes in Saint Michaels

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Cottage in St. Michaels
La Casita on Harris Creek, St. Michaels
1 bedroom, 2 beds, 1 private bathroom
29 Sept – 4 Oct
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4.98 out of 5 average rating, 203 reviews
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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 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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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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Guest house in St. Michaels
Secluded water, private sitting room, full bath!
1 bedroom, 2 single beds, 1 bathroom
17–22 Sept
5.0 out of 5 average rating, 45 reviews
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Home in St. Michaels
Miles Aweigh
3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
4.96 out of 5 average rating, 302 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, 175 reviews
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Home in Neavitt
Waterfront, Dog friendly, St Michaels home
2 bedrooms, 3 beds, 1 bathroom
21–26 Sept
4.94 out of 5 average rating, 107 reviews
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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 suite in Tilghman Island
Black Walnut Cove Retreat, Tilghman Island
1 bedroom, 4 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 181 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, 219 reviews
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Home in St. Michaels
Margaret Wells House
2 bedrooms, 2 beds, 2 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 53 reviews
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Cottage in Wittman
Perfect St. Michaels Getaway
2 bedrooms, 4 beds, 1.5 bathrooms
16–21 Oct
4.86 out of 5 average rating, 163 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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Home in Oxford
Stunning Chesapeake waterfront home
5 bedrooms, 9 beds, 4.5 bathrooms
27 Sept – 2 Oct
4.99 out of 5 average rating, 98 reviews
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Home in Easton
Newly Renovated Modern Waterfront Home
5 bedrooms, 13 beds, 5.5 bathrooms
17–22 Sept
5.0 out of 5 average rating, 46 reviews
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Guest house in Cambridge
The Loft at Sailor's Retreat. Waterfront Apartment
1 bedroom, 1 king bed, 1 bathroom
29 Oct – 3 Nov
4.99 out of 5 average rating, 122 reviews
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Home in Tilghman Island
Panoramic water views
2 bedrooms, 2 queen beds, 1 bathroom
19–24 Oct
4.95 out of 5 average rating, 43 reviews
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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, 230 reviews