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Search results; Over 1,000 homes in Saint Michaels

Room in St. Michaels
George Brooks House #3 King Jacuzzi
1 bedroom, 1 bed, 1 private bathroom
13–18 Sept
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4.69 out of 5 average rating, 16 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, 160 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, 174 reviews
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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, 301 reviews
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Home in St. Michaels
Ahoy St. Michaels! - A Historic Retreat
2 bedrooms, 3 beds
18–23 Oct
5.0 out of 5 average rating, 63 reviews
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Cottage in St. Michaels
La Casita on Harris Creek, St. Michaels
1 bedroom, 2 beds
23–28 Sept
4.98 out of 5 average rating, 202 reviews
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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, 16 reviews
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Home in St. Michaels
Historic Berkeley Hall in the heart of town
2 bedrooms, 2 beds
20–25 Sept
4.96 out of 5 average rating, 217 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
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
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
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Home in Easton
Eastern Shore Family Getaway
3 bedrooms, 6 beds
13–18 Sept
5.0 out of 5 average rating, 22 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 Easton
Newly Renovated Modern Waterfront Home
5 bedrooms, 13 beds
13–18 Sept
5.0 out of 5 average rating, 44 reviews
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Guest house in Easton
Chill in The Crib! Easton, Maryland
1 bedroom, 1 queen bed
6–11 Oct
4.99 out of 5 average rating, 657 reviews
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Guest house in St. Michaels
Secluded water, private sitting room, full bath!
1 bedroom, 2 single beds
4–9 Nov
5.0 out of 5 average rating, 45 reviews
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Home in Easton
Eastern Shore Retreat!
3 bedrooms, 3 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 58 reviews
Top guest favourite
Guest house in Stevensville
Waterfront-View of Bay from your Bed
1 queen bed
4–9 Oct
4.99 out of 5 average rating, 368 reviews