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Search results; Over 1,000 homes in Saint Michaels

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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
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Featured hotel
Hotel in St. Michaels
Standard double room
1 bedroom, 2 double beds
20–25 Sept
New place to stay
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Top guest favourite
Home in St. Michaels
Shipwrights Cottage in Town!
2 bedrooms, 3 beds
11–16 Oct
4.99 out of 5 average rating, 176 reviews
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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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Top guest favourite
Flat in St. Michaels
Blue Crab Lodge
2 bedrooms, 3 beds
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
25–30 Oct
5.0 out of 5 average rating, 65 reviews
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Cottage in Easton
Cottage on Solitude Creek, Hot Tub, Pool & Firepit
2 bedrooms, 3 beds
13–18 Oct
5.0 out of 5 average rating, 125 reviews
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Top guest favourite
Home in St. Michaels
Historic Berkeley Hall in the heart of town
2 bedrooms, 2 beds
25–30 Oct
4.96 out of 5 average rating, 219 reviews
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Top guest favourite
Home in St. Michaels
Margaret Wells House
2 bedrooms, 2 beds
27 Sept – 2 Oct
4.98 out of 5 average rating, 54 reviews
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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, 203 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, 89 reviews
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Home in St. Michaels
Dr. Miller house. Best location-in the heart town
2 bedrooms, 3 beds
4–9 Oct
4.92 out of 5 average rating, 230 reviews
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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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Guest favourite
Home in Wittman
Sewell Point Bungalow
3 bedrooms, 4 beds
4–9 Oct
4.94 out of 5 average rating, 17 reviews
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Top guest favourite
Flat in St. Michaels
Charming Studio in the heart of St. Michael's, MD.
2 beds
20–25 Sept
4.92 out of 5 average rating, 233 reviews
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Top guest favourite
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
Painted Sky
5 bedrooms, 8 beds
19–26 Jun
5.0 out of 5 average rating, 113 reviews
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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, 19 reviews
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Guest favourite
Guest house in Oxford
The Nichols House Cottage
1 double bed
1–6 Nov
4.92 out of 5 average rating, 146 reviews