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Search results; Over 1,000 homes in Saint Michaels

Top guest favourite
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, 171 reviews
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, 158 reviews
Featured hotel
Room in St. Michaels
Standard queen room
1 queen bed, 1 bathroom
6–11 Sept
New place to stay
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
Top guest favourite
Home in St. Michaels
Ahoy St. Michaels! - A Historic Retreat
2 bedrooms, 3 beds, 2.5 bathrooms
3–8 Sept
5.0 out of 5 average rating, 57 reviews
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
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, 49 reviews
Top guest favourite
Home in St. Michaels
Historic Berkeley Hall in the heart of town
2 bedrooms, 2 beds, 1.5 bathrooms
8–13 Sept
4.96 out of 5 average rating, 215 reviews
Guest favourite
Home in Easton
St. Michaels Waterfront Home with Private Dock
3 bedrooms, 6 beds, 2.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 18 reviews
Superhost
Home in Stevensville
Private & Peaceful | Water Views, Big Deck, Games
3 bedrooms, 5 beds, 3 bathrooms
13–18 Sept
New place to stay
Top guest favourite
Home in Tilghman Island
The Getaway
3 bedrooms, 3 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 31 reviews
Superhost
Boutique hotel in Oxford
Sandaway Suites & Beach | Town View Eastern Shore
1 bedroom, 1 queen bed, 1 bathroom
1–6 Sept
4.8 out of 5 average rating, 5 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, 299 reviews
Top guest favourite
Home in St. Michaels
Dr. Miller house. Best location-in the heart town
2 bedrooms, 3 beds, 1.5 bathrooms
20–25 Sept
4.92 out of 5 average rating, 224 reviews
Top guest favourite
Flat in St. Michaels
Charming Studio in the heart of St. Michael's, MD.
2 beds, 1 bathroom
20–25 Sept
4.92 out of 5 average rating, 230 reviews
Guest favourite
Home in Chester
Kent Island Escape
2 bedrooms, 4 beds, 2 bathrooms
5–10 Oct
4.98 out of 5 average rating, 43 reviews
Guest favourite
Home in Newcomb
Saint Michaels Waterfront Home
2 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.99 out of 5 average rating, 70 reviews
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
Top guest favourite
Guest suite in Tilghman Island
Black Walnut Cove Retreat, Tilghman Island
1 bedroom, 4 beds, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 181 reviews