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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
2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
4.97 out of 5 average rating, 150 reviews
Top guest favourite
Home in Saint Michaels
Miles Aweigh
3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
4.97 out of 5 average rating, 290 reviews
Top guest favourite
Home in Saint Michaels
Shipwrights Cottage in Town!
2 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
4.99 out of 5 average rating, 162 reviews
Top guest favourite
Home in Saint Michaels
Private&Cozy/3br+2ba/1mi to town
3 bedrooms, 3 beds, 2 bathrooms
27 Jul – 1 Aug
4.94 out of 5 average rating, 79 reviews
Guest favourite
Home in Grasonville
Private Waterfront Home W/ Hot Tub, Dock & Kayaks
3 bedrooms, 3 queen beds, 2 bathrooms
13–18 Jul
4.95 out of 5 average rating, 306 reviews
Top guest favourite
Home in Saint Michaels
Ahoy St. Michaels! - A Historic Retreat
2 bedrooms, 3 beds, 2.5 bathrooms
2–7 Aug
5.0 out of 5 average rating, 51 reviews
Top guest favourite
Home in Saint Michaels
Margaret Wells House
2 bedrooms, 2 beds, 2 bathrooms
19–24 Jul
4.98 out of 5 average rating, 43 reviews
Guest favourite
Flat in Saint Michaels
Downtown St. Michaels | Porch + Pet-Friendly
3 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
4.94 out of 5 average rating, 18 reviews
Top guest favourite
Room in Saint Michaels
Secluded water - bedroom, sitting room, full bath!
2 single beds, 1 bathroom
27 Jul – 1 Aug
5.0 out of 5 average rating, 37 reviews
Home in Easton
Royal Oak Roadhouse
3 bedrooms, 3 beds, 2.5 bathrooms
19–24 Jul
Guest favourite
Home in Easton
St. Michaels Waterfront Home with Private Dock
3 bedrooms, 6 beds, 2.5 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Cottage in Easton
Cottage on Solitude Creek, Hot Tub, Pool & Firepit
2 bedrooms, 3 beds, 2 bathrooms
13–18 Oct
5.0 out of 5 average rating, 123 reviews
Top guest favourite
Home in Saint Michaels
Dr. Miller house. Best location-in the heart town
2 bedrooms, 3 beds, 1.5 bathrooms
23–28 Aug
4.92 out of 5 average rating, 216 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, 36 reviews
Top guest favourite
Cottage in Wittman
"Wittman Cottage"
3 bedrooms, 3 beds, 2 bathrooms
27 Oct – 1 Nov
4.9 out of 5 average rating, 194 reviews
Top guest favourite
Home in Tilghman Island
Panoramic water views
2 bedrooms, 2 queen beds, 1 bathroom
19–24 Jul
4.95 out of 5 average rating, 42 reviews
Top guest favourite
Cottage in Saint Michaels
La Casita on Harris Creek, St. Michaels
1 bedroom, 2 beds, 1 bathroom
28 Jul – 2 Aug
4.97 out of 5 average rating, 192 reviews
Guest favourite
Home in Sherwood
Punch Point boasts a sandy beach w/ pool and pier
5 bedrooms, 5 beds, 4.5 bathrooms
22–27 Aug
5.0 out of 5 average rating, 19 reviews