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Search results; Over 1,000 homes in Saint Michaels

Top guest favourite
Home in Saint Michaels
SM's Premier Rental Heated Pool (opens 4/3)
2 bedrooms, 2 beds, 2 private bathrooms
30 Aug – 4 Sept
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4.98 out of 5 average rating, 112 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
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
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 Saint Michaels
Shipwrights Cottage in Town!
4.99 out of 5 average rating, 159 reviews, 2 bedrooms, 3 beds, 2 bathrooms
12–17 Jul
Guest favourite
Houseboat in Cambridge
Loveboat, Where Love Meets The Waves.
5.0 out of 5 average rating, 5 reviews, 1 bedroom, 1 bed, 1 bathroom
8–13 Jul
Top guest favourite
Home in Tilghman Island
The Getaway
5.0 out of 5 average rating, 26 reviews, 3 bedrooms, 3 beds, 2 bathrooms
8–13 Sept
Home in Bozman
Brand-New Pool! Waterfront Bozman Village Home
4.83 out of 5 average rating, 12 reviews, 4 bedrooms, 6 beds, 2.5 bathrooms
4–9 Oct
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
21–26 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 Saint Michaels
Private&Cozy/3br+2ba/1mi to town
4.94 out of 5 average rating, 78 reviews, 3 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
Flat in Saint Michaels
Charming Studio in the heart of St. Michael's, MD.
4.92 out of 5 average rating, 222 reviews, 2 beds, 1 bathroom
12–17 Jul
Guest favourite
Home in Grasonville
Private Waterfront Home W/ Hot Tub, Dock & Kayaks
4.95 out of 5 average rating, 304 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
Cottage in Easton
Cottage on Solitude Creek, Hot Tub, Pool & Firepit
5.0 out of 5 average rating, 123 reviews, 2 bedrooms, 3 beds, 2 bathrooms
13–18 Oct
Top guest favourite
Home in Saint Michaels
Miles Aweigh
4.97 out of 5 average rating, 289 reviews, 3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
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
7–12 Oct
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