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Search results; Over 1,000 homes in Saint Michaels

Top guest favourite
Cottage in Saint Michaels
The Little Anchor Cottage, St. Michaels, MD
2 bedrooms, 3 beds, 1 private bathroom
15–20 Aug
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4.97 out of 5 average rating, 292 reviews
Top guest favourite
Flat in Saint Michaels
Blue Crab Lodge
4.97 out of 5 average rating, 150 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
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Home in Saint Michaels
Shipwrights Cottage in Town!
4.99 out of 5 average rating, 161 reviews, 2 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
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Home in Saint Michaels
Miles Aweigh
4.97 out of 5 average rating, 289 reviews, 3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
Top guest favourite
Home in Saint Michaels
Private&Cozy/3br+2ba/1mi to town
4.94 out of 5 average rating, 79 reviews, 3 bedrooms, 3 beds, 2 bathrooms
12–17 Jul
Top guest favourite
Home in Saint Michaels
Ahoy St. Michaels! - A Historic Retreat
5.0 out of 5 average rating, 51 reviews, 2 bedrooms, 3 beds, 2.5 bathrooms
2–7 Aug
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Home in Saint Michaels
Margaret Wells House
4.98 out of 5 average rating, 42 reviews, 2 bedrooms, 2 beds, 2 bathrooms
19–24 Jul
Top guest favourite
Cottage in Saint Michaels
La Casita on Harris Creek, St. Michaels
4.97 out of 5 average rating, 191 reviews, 1 bedroom, 2 beds, 1 bathroom
28 Jul – 2 Aug
Top guest favourite
Room in Saint Michaels
Secluded water - bedroom, sitting room, full bath!
5.0 out of 5 average rating, 36 reviews, 2 single beds, 1 bathroom
21–26 Jul
Guest favourite
Home in Grasonville
Private Waterfront Home W/ Hot Tub, Dock & Kayaks
4.95 out of 5 average rating, 305 reviews, 3 bedrooms, 3 beds, 2 bathrooms
12–17 Jul
Guest favourite
Flat in Saint Michaels
Downtown St. Michaels | Porch + Pet-Friendly
4.94 out of 5 average rating, 18 reviews, 3 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
Guest favourite
Room in Saint Michaels
The Snuggery Inn & Suites
4.8 out of 5 average rating, 5 reviews, 1 queen bed, 1 bathroom
12–17 Jul
Top guest favourite
Home in Saint Michaels
SM's Premier Rental Heated Pool (opens 4/3)
4.98 out of 5 average rating, 112 reviews, 2 bedrooms, 2 beds, 2 bathrooms
30 Aug – 4 Sept
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Home in Tilghman Island
Panoramic water views
4.95 out of 5 average rating, 42 reviews, 2 bedrooms, 2 beds, 1 bathroom
19–24 Jul
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Home in Tilghman Island
The Getaway
5.0 out of 5 average rating, 26 reviews, 3 bedrooms, 3 beds, 2 bathrooms
8–13 Sept
Guest favourite
Cabin in Saint Michaels
True St. Michaels 6 Acre Waterfront w/heated pool
4.99 out of 5 average rating, 123 reviews, 5 bedrooms, 11 beds, 3 bathrooms
16–21 Jul
Top guest favourite
Home in Saint Michaels
Dr. Miller house. Best location-in the heart town
4.92 out of 5 average rating, 216 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
19–24 Jul
Top guest favourite
Flat in Easton
3Br/1Ba Pondview Longsdale House
4.95 out of 5 average rating, 22 reviews, 3 bedrooms, 3 beds, 1 bathroom
16–21 Jul
Guest favourite
Flat in Saint Michaels
Charming Apt. in St. Michaels
4.97 out of 5 average rating, 93 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
26–31 Jul