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Search results; Over 1,000 homes in Saint Michaels

Top guest favourite
Cottage in St. Michaels
La Casita on Harris Creek, St. Michaels
1 bedroom, 2 beds, 1 private bathroom
13–18 Sept
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4.97 out of 5 average rating, 195 reviews
Top guest favourite
Flat in St. Michaels
Blue Crab Lodge
2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
4.97 out of 5 average rating, 157 reviews
Featured hotel
Room in St. Michaels
Standard queen room
1 queen bed, 1 bathroom
16–21 Aug
New place to stay
Top guest favourite
Home in St. Michaels
Shipwrights Cottage in Town!
2 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
4.99 out of 5 average rating, 169 reviews
Top guest favourite
Guest house in Stevensville
Waterfront-View of Bay from your Bed
1 queen bed, 1 bathroom
21–26 Sept
4.99 out of 5 average rating, 360 reviews
Top guest favourite
Place to stay in Cambridge
Wye Three Oaks
2 bedrooms, 4 beds, 1 bathroom
7–12 Sept
4.96 out of 5 average rating, 104 reviews
Top guest favourite
Cottage in St. Michaels
The Little Anchor Cottage, St. Michaels, MD
2 bedrooms, 3 beds, 1 bathroom
24–29 Aug
4.97 out of 5 average rating, 297 reviews
Top guest favourite
Home in Bozman
The Cottage at Broad Creek
1 bedroom, 1 bed, 1.5 bathrooms
11–16 Sept
5.0 out of 5 average rating, 48 reviews
Top guest favourite
Home in St. Michaels
Historic Berkeley Hall in the heart of town
2 bedrooms, 2 beds, 1.5 bathrooms
6–11 Sept
4.96 out of 5 average rating, 212 reviews
Top guest favourite
Flat in St. Michaels
Charming Studio in the heart of St. Michael's, MD.
2 beds, 1 bathroom
30 Aug – 4 Sept
4.92 out of 5 average rating, 229 reviews
Top guest favourite
Flat in Chester
Cozy Waterfront Apartment Chester, MD
1 bedroom, 1 queen bed, 1 bathroom
16–21 Aug
4.96 out of 5 average rating, 297 reviews
Guest favourite
Houseboat in Cambridge
Loveboat, Where Love Meets The Waves.
1 bedroom, 1 bed, 1 bathroom
22–27 Aug
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Houseboat in Solomons
Good Vibe Villa, Tiny houseboat
1 queen bed, 1 bathroom
23–28 Aug
4.97 out of 5 average rating, 197 reviews
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, 297 reviews
Top guest favourite
Guest suite in Tilghman Island
Black Walnut Cove Retreat, Tilghman Island
1 bedroom, 4 beds, 1 bathroom
23–28 Aug
4.97 out of 5 average rating, 180 reviews
Top guest favourite
Home in Easton
Eastern Shore Retreat!
3 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
5.0 out of 5 average rating, 56 reviews
Top guest favourite
Home in St. Michaels
Dr. Miller house. Best location-in the heart town
2 bedrooms, 3 beds, 1.5 bathrooms
30 Aug – 4 Sept
4.92 out of 5 average rating, 224 reviews
Townhouse in Queenstown
Golf, Kayaks, Outlets, Water Access, Fire Pit!
3 bedrooms, 4 beds, 1.5 bathrooms
17–22 Aug
New place to stay
Guest favourite
Home in St. Michaels
Cozy, Family-Friendly Log Cabin-St. Michaels
4 bedrooms, 5 beds, 3 bathrooms
25–30 Aug
5.0 out of 5 average rating, 15 reviews