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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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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
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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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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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
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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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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Flat in St. Michaels
Charming Studio in the heart of St. Michael's, MD.
2 beds, 1 bathroom
20–25 Sept
4.92 out of 5 average rating, 233 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, 17 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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Home in St. Michaels
Margaret Wells House
2 bedrooms, 2 beds, 2 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 54 reviews
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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 Easton
Eastern Shore Retreat!
3 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 58 reviews
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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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Guest house in Stevensville
Waterfront-View of Bay from your Bed
1 queen bed, 1 bathroom
4–9 Oct
4.99 out of 5 average rating, 371 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, 231 reviews
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Home in Easton
Painted Sky
5 bedrooms, 8 beds, 4.5 bathrooms
19–26 Jun
5.0 out of 5 average rating, 113 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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Houseboat in Cambridge
Loveboat, Where Love Meets The Waves.
1 bedroom, 1 bed, 1 bathroom
27 Sept – 2 Oct
4.9 out of 5 average rating, 30 reviews