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Search results; Over 1,000 homes in Saint Michaels

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Top guest favourite
Flat in St. Michaels
Blue Crab Lodge
2 bedrooms, 3 beds, 1 private bathroom
18–23 Oct
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4.98 out of 5 average rating, 161 reviews
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Guest favourite
Flat in St. Michaels
Downtown St. Michaels | Porch + Pet-Friendly
3 bedrooms, 4 beds
4–9 Oct
4.96 out of 5 average rating, 25 reviews
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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, 177 reviews
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Top guest favourite
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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Top guest favourite
Cottage in St. Michaels
The Little Anchor Cottage, St. Michaels, MD
2 bedrooms, 3 beds
18–23 Oct
4.97 out of 5 average rating, 303 reviews
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Top guest favourite
Home in St. Michaels
Grace Cottage, Saint Michaels Walk to everything!
2 bedrooms, 2 king beds
4–9 Oct
5.0 out of 5 average rating, 17 reviews
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Guest favourite
Home in Sherwood
Chesapeake Mansion-heated pool 30acre waterfront
8 bedrooms, 11 beds
5–10 Oct
4.99 out of 5 average rating, 81 reviews
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Home in Bozman
Brand-New Pool! Waterfront Bozman Village Home
4 bedrooms, 6 beds
4–9 Oct
4.81 out of 5 average rating, 16 reviews
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Guest favourite
Home in St. Michaels
Summer Retreat — Pool, Hot Tub & Outdoor Oasis
3 bedrooms, 4 beds
1–6 Oct
4.86 out of 5 average rating, 22 reviews
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Top guest favourite
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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Houseboat in Cambridge
Loveboat, Where Love Meets The Waves.
1 bedroom, 1 bed
25–30 Oct
4.9 out of 5 average rating, 31 reviews
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Top guest favourite
Home in Easton
Eastern Shore Retreat!
3 bedrooms, 3 beds
1–6 Oct
5.0 out of 5 average rating, 58 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, 46 reviews
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Guest favourite
Home in Sherwood
Punch Point boasts a sandy beach w/ pool and pier
5 bedrooms, 5 beds
1–6 Oct
5.0 out of 5 average rating, 24 reviews
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Guest favourite
Cabin in St. Michaels
True St. Michaels 6 Acre Waterfront w/heated pool
5 bedrooms, 11 beds
4–9 Oct
4.99 out of 5 average rating, 127 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
4–9 Oct
4.92 out of 5 average rating, 231 reviews
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Guest favourite
Home in St. Michaels
Walk to Everything House
3 bedrooms, 4 beds
4–9 Oct
4.89 out of 5 average rating, 72 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
Home in Cambridge
Relaxing Retreat on the Hudson
5 bedrooms, 5 beds
4–9 Oct
4.96 out of 5 average rating, 81 reviews