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Search results; Over 1,000 homes in Saint Michaels

Resort in St. Michaels
St. Michaels Harbour Inn - Waterfront King Room
Studio, 1 bed, 1 bathroom
20–25 Sept
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4.85 out of 5 average rating, 27 reviews
Top guest favourite
Flat in St. Michaels
Blue Crab Lodge
2 bedrooms, 3 beds
13–18 Sept
4.98 out of 5 average rating, 161 reviews
Guest favourite
Home in St. Michaels
Miles Aweigh
3 bedrooms, 4 beds
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
11–16 Oct
4.99 out of 5 average rating, 175 reviews
Top guest favourite
Cottage in St. Michaels
The Little Anchor Cottage, St. Michaels, MD
2 bedrooms, 3 beds
4–9 Oct
4.97 out of 5 average rating, 303 reviews
Top guest favourite
Home in St. Michaels
Grace Cottage, Saint Michaels Walk to everything!
2 bedrooms, 2 king beds
20–25 Sept
5.0 out of 5 average rating, 17 reviews
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Home in St. Michaels
Ahoy St. Michaels! - A Historic Retreat
2 bedrooms, 3 beds
25–30 Oct
5.0 out of 5 average rating, 63 reviews
Guest favourite
Flat in St. Michaels
Downtown St. Michaels | Porch + Pet-Friendly
3 bedrooms, 4 beds
27 Sept – 2 Oct
4.96 out of 5 average rating, 25 reviews
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Home in St. Michaels
Margaret Wells House
2 bedrooms, 2 beds
27 Sept – 2 Oct
4.98 out of 5 average rating, 52 reviews
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Home in St. Michaels
Private&Cozy/3br+2ba/1mi to town
3 bedrooms, 3 beds
25–30 Oct
4.94 out of 5 average rating, 88 reviews
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Home in St. Michaels
Historic Berkeley Hall in the heart of town
2 bedrooms, 2 beds
4–9 Oct
4.96 out of 5 average rating, 218 reviews
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Home in St. Michaels
Dr. Miller house. Best location-in the heart town
2 bedrooms, 3 beds
13–18 Sept
4.92 out of 5 average rating, 229 reviews
Guest favourite
Home in St. Michaels
Cozy, Family-Friendly Log Cabin-St. Michaels
4 bedrooms, 5 beds
19–24 Sept
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Guest house in Easton
Chill in The Crib! Easton, Maryland
1 bedroom, 1 queen bed
30 Nov – 5 Dec
4.99 out of 5 average rating, 657 reviews
Guest favourite
Home in Wittman
Sewell Point Bungalow
3 bedrooms, 4 beds
4–9 Oct
4.94 out of 5 average rating, 16 reviews
Top guest favourite
Home in Tilghman Island
Panoramic water views
2 bedrooms, 2 queen beds
19–24 Oct
4.95 out of 5 average rating, 43 reviews
Superhost
Home in St. Michaels
St. Michaels Waterfront Home with Pool
4 bedrooms, 5 beds
23–28 Dec
Top guest favourite
Cottage in St. Michaels
Lovely Waterfront Cottage on 2 acres, St. Michaels
3 bedrooms, 5 beds
19–24 Sept
4.97 out of 5 average rating, 35 reviews
Top guest favourite
Cottage in St. Michaels
La Casita on Harris Creek, St. Michaels
1 bedroom, 2 beds
29 Sept – 4 Oct
4.98 out of 5 average rating, 202 reviews