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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
4–9 Oct
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4.97 out of 5 average rating, 301 reviews
Featured hotel
Room in St. Michaels
Standard double room
2 double beds, 1 bathroom
7–12 Sept
New place to stay
Top guest favourite
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, 61 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
13–18 Sept
4.98 out of 5 average rating, 160 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, 17 reviews
Top guest favourite
Cottage in St. Michaels
La Casita on Harris Creek, St. Michaels
1 bedroom, 2 beds, 1 bathroom
23–28 Sept
4.98 out of 5 average rating, 200 reviews
Top guest favourite
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, 97 reviews
Top guest favourite
Guest house in St. Michaels
Secluded water, private sitting room, full bath!
1 bedroom, 2 single beds, 1 bathroom
4–9 Nov
5.0 out of 5 average rating, 45 reviews
Guest favourite
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
Top guest favourite
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
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, 174 reviews
Top guest favourite
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
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
Top guest favourite
Home in Easton
Arcadia Shores On The Cove
4 bedrooms, 7 beds, 4 bathrooms
5–10 Sept
4.95 out of 5 average rating, 19 reviews
Home in Easton
Royal Oak Roadhouse
3 bedrooms, 3 beds, 2.5 bathrooms
27 Sept – 2 Oct
Top guest favourite
Home in Easton
Eastern Shore Retreat!
3 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 57 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, 52 reviews
Guest favourite
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