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Search results; Over 1,000 homes in Saint Michaels

Top guest favourite
Cottage in St. Michaels
The Little Anchor Cottage, St. Michaels, MD
2 bedrooms, 3 beds, 1 private bathroom
4–9 Oct
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4.97 out of 5 average rating, 301 reviews
Featured hotel
Room in St. Michaels
Standard queen room
1 queen bed, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 3 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
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, 202 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
Home in Oxford
Stunning Chesapeake waterfront home
5 bedrooms, 9 beds, 4.5 bathrooms
27 Sept – 2 Oct
4.99 out of 5 average rating, 98 reviews
Top guest favourite
Home in St. Michaels
Ahoy St. Michaels! - A Historic Retreat
2 bedrooms, 3 beds, 2.5 bathrooms
18–23 Oct
5.0 out of 5 average rating, 63 reviews
Top guest favourite
Home in Easton
Arcadia Shores On The Cove
4 bedrooms, 7 beds, 4 bathrooms
13–18 Sept
4.95 out of 5 average rating, 20 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, 232 reviews
Top guest favourite
Guest house in St. Michaels
Secluded water, private sitting room, full bath!
1 bedroom, 2 single beds, 1 bathroom
4–9 Nov
5.0 out of 5 average rating, 45 reviews
Top guest favourite
Home in Tilghman Island
Panoramic water views
2 bedrooms, 2 queen beds, 1 bathroom
19–24 Oct
4.95 out of 5 average rating, 43 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, 58 reviews
Top guest favourite
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
Home in Easton
Royal Oak Roadhouse
3 bedrooms, 3 beds, 2.5 bathrooms
27 Sept – 2 Oct
Guest favourite
Home in Newcomb
Saint Michaels Waterfront Home
2 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.97 out of 5 average rating, 74 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
Top guest favourite
Home in St. Michaels
Historic Berkeley Hall in the heart of town
2 bedrooms, 2 beds, 1.5 bathrooms
4–9 Oct
4.96 out of 5 average rating, 217 reviews
Superhost
Home in Stevensville
Private & Peaceful Water Views, Big Deck, Games
3 bedrooms, 5 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
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