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Search results; Over 1,000 homes in Saint Michaels

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Home in St. Michaels
Shipwrights Cottage in Town!
2 bedrooms, 3 beds, 2 bathrooms
11–16 Oct
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4.99 out of 5 average rating, 173 reviews
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Featured hotel
Room in St. Michaels
Standard double room
2 double beds, 1 bathroom
1–6 Sept
New place to stay
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Top guest favourite
Flat in St. Michaels
Blue Crab Lodge
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 159 reviews
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Top guest favourite
Home in St. Michaels
Miles Aweigh
3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
4.97 out of 5 average rating, 299 reviews
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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, 88 reviews
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Top guest favourite
Home in Easton
4 bdrm, 3 bath, 2,700 sqft whole house on 1 acre
4 bedrooms, 4 beds, 3 bathrooms
1–6 Sept
4.97 out of 5 average rating, 99 reviews
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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
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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, 59 reviews
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Superhost
Home in St. Michaels
St. Michaels Waterfront Home with Pool
4 bedrooms, 5 beds, 4.5 bathrooms
1–6 Oct
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Top guest favourite
Cottage in St. Michaels
The Little Anchor Cottage, St. Michaels, MD
2 bedrooms, 3 beds, 1 bathroom
4–9 Oct
4.97 out of 5 average rating, 301 reviews
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Guest favourite
Cabin in St. Michaels
True St. Michaels 6 Acre Waterfront w/heated pool
5 bedrooms, 11 beds, 3 bathrooms
7–12 Sept
4.99 out of 5 average rating, 124 reviews
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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
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Guest favourite
Room in St. Michaels
The Snuggery Inn & Suites
1 queen bed, 1 bathroom
1–6 Sept
4.86 out of 5 average rating, 7 reviews
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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, 15 reviews
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Guest favourite
Home in Sherwood
Chesapeake Mansion-heated pool 30acre waterfront
8 bedrooms, 11 beds, 11 bathrooms
5–10 Oct
4.99 out of 5 average rating, 79 reviews
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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, 56 reviews
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Top guest favourite
Cottage in St. Michaels
La Casita on Harris Creek, St. Michaels
1 bedroom, 2 beds, 1 bathroom
23–28 Sept
4.97 out of 5 average rating, 199 reviews
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Top guest favourite
Home in St. Michaels
Dr. Miller house. Best location-in the heart town
2 bedrooms, 3 beds, 1.5 bathrooms
13–18 Sept
4.92 out of 5 average rating, 225 reviews
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Guest favourite
Home in Wittman
Eastern Shore Cottage – Near St. Michaels Gateway
3 bedrooms, 3 beds, 1 bathroom
1–6 Sept
4.94 out of 5 average rating, 16 reviews