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Search results; Over 1,000 homes in Saint Michaels

Top guest favourite
Cottage in St. Michaels
The Little Anchor Cottage, St. Michaels, MD
2 bedrooms, 3 beds, 1 private bathroom
18–23 Oct
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4.97 out of 5 average rating, 303 reviews
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, 175 reviews
Guest favourite
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
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, 161 reviews
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
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
Featured hotel
Hotel in St. Michaels
Standard double room
1 bedroom, 2 double beds, 1 bathroom
20–25 Sept
New place to stay
Top guest favourite
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
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
Top guest favourite
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
Guest favourite
Home in St. Michaels
Cozy, Family-Friendly Log Cabin-St. Michaels
4 bedrooms, 5 beds, 3 bathrooms
19–24 Sept
5.0 out of 5 average rating, 18 reviews
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, 230 reviews
Top guest favourite
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
Top guest favourite
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
Top guest favourite
Home in Easton
Newly Renovated Modern Waterfront Home
5 bedrooms, 13 beds, 5.5 bathrooms
16–21 Sept
5.0 out of 5 average rating, 46 reviews
Guest favourite
Home in Wittman
Sewell Point Bungalow
3 bedrooms, 4 beds, 1 bathroom
4–9 Oct
4.94 out of 5 average rating, 16 reviews
Home in Bozman
Brand-New Pool! Waterfront Bozman Village Home
4 bedrooms, 6 beds, 2.5 bathrooms
4–9 Oct
4.81 out of 5 average rating, 16 reviews
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, 126 reviews
Superhost
Home in St. Michaels
St. Michaels Waterfront Home with Pool
4 bedrooms, 5 beds, 4.5 bathrooms
23–28 Dec