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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
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
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
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
4 bedrooms, 6 beds, 3 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Flat in St. Michaels
Charming Studio in the heart of St. Michael's, MD.
2 beds, 1 bathroom
16–21 Aug
4.92 out of 5 average rating, 229 reviews
Superhost
Home in St. Michaels
St. Michaels Waterfront Home with Pool
4 bedrooms, 5 beds, 4.5 bathrooms
1–6 Oct
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
Barn in Queenstown
Waterfront Modern Guest Barn
3 bedrooms, 5 beds, 2.5 bathrooms
16–21 Aug
4.99 out of 5 average rating, 85 reviews
Home in Chester
NEW I Waterfront, HotTub, Dock, Fire Pit, GameRoom
4 bedrooms, 4 king beds, 3.5 bathrooms
30 Aug – 4 Sept
New place to stay
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, 198 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, 42 reviews
Guest favourite
Cabin in St. Michaels
True St. Michaels 6 Acre Waterfront w/heated pool
5 bedrooms, 11 beds, 3 bathrooms
7–12 Sept
4.99 out of 5 average rating, 124 reviews
Guest favourite
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, 85 reviews
Top guest favourite
Cottage in Easton
Cottage on Solitude Creek, Hot Tub, Pool & Firepit
2 bedrooms, 3 beds, 2 bathrooms
3–8 Nov
5.0 out of 5 average rating, 125 reviews
Top 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
Guest favourite
Hotel room in Oxford
Sandaway Suites & Beach Waterfront Hotel Oxford MD
1 bedroom, 1 king bed, 1 bathroom
23–28 Aug
4.95 out of 5 average rating, 59 reviews
Top guest favourite
Home in Leonardtown
Water's Edge Cottage | Luxury Retreat
2 bedrooms, 2 beds, 2 bathrooms
26–31 Oct
4.99 out of 5 average rating, 137 reviews
Home in Easton
Royal Oak Roadhouse
3 bedrooms, 3 beds, 2.5 bathrooms
30 Aug – 4 Sept