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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
30 Jul – 4 Aug
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4.97 out of 5 average rating, 291 reviews
Top guest favourite
Flat in Saint Michaels
Blue Crab Lodge
4.97 out of 5 average rating, 147 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
Top guest favourite
Cottage in Saint Michaels
La Casita on Harris Creek, St. Michaels
4.97 out of 5 average rating, 191 reviews, 1 bedroom, 2 beds, 1 bathroom
28 Jul – 2 Aug
Top guest favourite
Home in Bozman
The Cottage at Broad Creek
5.0 out of 5 average rating, 39 reviews, 1 bedroom, 1 bed, 1.5 bathrooms
5–10 Jul
Top guest favourite
Home in Saint Michaels
Shipwrights Cottage in Town!
4.99 out of 5 average rating, 158 reviews, 2 bedrooms, 3 beds, 2 bathrooms
12–17 Jul
Top guest favourite
Cottage in Leonardtown
Beach Front and 'Perfectly Placed'
4.96 out of 5 average rating, 260 reviews, 2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
Top guest favourite
Home in Cambridge
Relaxing Retreat on the Hudson
4.96 out of 5 average rating, 71 reviews, 5 bedrooms, 5 beds, 2 bathrooms
24–29 Aug
Guest favourite
Home in Grasonville
Private Waterfront Home W/ Hot Tub, Dock & Kayaks
4.95 out of 5 average rating, 303 reviews, 3 bedrooms, 3 beds, 2 bathrooms
16–21 Aug
Top guest favourite
Home in Cambridge
Sunset Breezes - quiet waterfront retreat
4.99 out of 5 average rating, 218 reviews, 3 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Cabin in Saint Michaels
True St. Michaels 6 Acre Waterfront w/heated pool
4.99 out of 5 average rating, 122 reviews, 5 bedrooms, 11 beds, 3 bathrooms
16–21 Jul
Guest favourite
Cottage in North Beach
Cozy Waterfront Cottage - Pet Friendly
4.95 out of 5 average rating, 92 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Sept
Guest favourite
Hotel room in Oxford
Sandaway Suites & Beach Waterfront Hotel Oxford MD
4.96 out of 5 average rating, 51 reviews, 1 bedroom, 1 bed, 1 bathroom
22–27 Jul
Top guest favourite
Cottage in Easton
Cottage on Solitude Creek, Hot Tub, Pool & Firepit
5.0 out of 5 average rating, 122 reviews, 2 bedrooms, 3 beds, 2 bathrooms
8–13 Aug
Superhost
Home in Royal Oak
Waterfront Paradise | Pool, Views & Serenity
5.0 out of 5 average rating, 6 reviews, 4 bedrooms, 7 beds, 4.5 bathrooms
6–11 Sept
Top guest favourite
Home in Shady Side
Canary Pointe-A popular getaway for 2!
4.98 out of 5 average rating, 264 reviews, 1 bedroom, 2 beds, 1 bathroom
27 Jul – 1 Aug
Top guest favourite
Room in Saint Michaels
Secluded water - bedroom, sitting room, full bath!
5.0 out of 5 average rating, 36 reviews, 2 single beds, 1 bathroom
27 Jul – 1 Aug
Home in McDaniel
Skipjack House | an ESVR property
3 bedrooms, 4 beds, 2 bathrooms
9–14 Jul
Top guest favourite
Home in Saint Michaels
Margaret Wells House
4.98 out of 5 average rating, 42 reviews, 2 bedrooms, 2 beds, 2 bathrooms
19–24 Jul
Top guest favourite
Guest house in Stevensville
Waterfront-View of Bay from your Bed
4.99 out of 5 average rating, 349 reviews, 1 bed, 1 bathroom
7–12 Sept