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Search results; Over 1,000 homes in Saint Michaels

Guest favourite
Cabin in St. Michaels
True St. Michaels 6 Acre Waterfront w/heated pool
5 bedrooms, 11 beds, 3 private bathrooms
4–9 Oct
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4.99 out of 5 average rating, 125 reviews
Guest favourite
Home in St. Michaels
Miles Aweigh
3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
4.96 out of 5 average rating, 302 reviews
Top guest favourite
Flat in St. Michaels
Blue Crab Lodge
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 160 reviews
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Home in St. Michaels
Shipwrights Cottage in Town!
2 bedrooms, 3 beds, 2 bathrooms
11–16 Oct
4.99 out of 5 average rating, 174 reviews
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, 62 reviews
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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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, 16 reviews
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Home in St. Michaels
Margaret Wells House
2 bedrooms, 2 beds, 2 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 52 reviews
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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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
Guest favourite
Home in St. Michaels
Cozy, Family-Friendly Log Cabin-St. Michaels
4 bedrooms, 5 beds, 3 bathrooms
19–24 Sept
5.0 out of 5 average rating, 17 reviews
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, 228 reviews
Top guest favourite
Cottage in St. Michaels
La Casita on Harris Creek, St. Michaels
1 bedroom, 2 beds, 1 bathroom
23–28 Sept
4.98 out of 5 average rating, 201 reviews
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
Top guest favourite
Home in Easton
Newly Renovated Modern Waterfront Home
5 bedrooms, 13 beds, 5.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 44 reviews
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Home in Easton
Eastern Shore Retreat!
3 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 58 reviews
Guest favourite
Home in St. Michaels
Summer Retreat — Pool, Hot Tub & Outdoor Oasis
3 bedrooms, 4 beds, 3.5 bathrooms
20–25 Sept
4.86 out of 5 average rating, 21 reviews
Top guest favourite
Guest house in Easton
Chill in The Crib! Easton, Maryland
1 bedroom, 1 queen bed, 1 bathroom
30 Nov – 5 Dec
4.99 out of 5 average rating, 657 reviews
Guest favourite
Home in Wittman
Sewell Point Bungalow
3 bedrooms, 4 beds, 1 bathroom
4–9 Oct
4.94 out of 5 average rating, 16 reviews