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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
2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
4.97 out of 5 average rating, 147 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, 191 reviews
Guest favourite
Home in Wittman
Waterfront cottage in Wittman Maryland
2 bedrooms, 3 beds, 1 bathroom
22–27 Aug
4.92 out of 5 average rating, 13 reviews
Top guest favourite
Home in Saint Michaels
Shipwrights Cottage in Town!
2 bedrooms, 3 beds, 2 bathrooms
12–17 Jul
4.99 out of 5 average rating, 159 reviews
Home in Bozman
Brand-New Pool! Waterfront Bozman Village Home
4 bedrooms, 6 beds, 2.5 bathrooms
4–9 Oct
4.83 out of 5 average rating, 12 reviews
Top guest favourite
Home in Tilghman Island
The Getaway
3 bedrooms, 3 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Home in Cambridge
Relaxing Retreat on the Hudson
5 bedrooms, 5 beds, 2 bathrooms
24–29 Aug
4.96 out of 5 average rating, 71 reviews
Guest favourite
Home in Grasonville
Private Waterfront Home W/ Hot Tub, Dock & Kayaks
3 bedrooms, 3 queen beds, 2 bathrooms
12–17 Jul
4.95 out of 5 average rating, 304 reviews
Guest favourite
Home in Saint Michaels
Private&Cozy/3br+2ba/1mi to town
3 bedrooms, 3 beds, 2 bathrooms
12–17 Jul
4.94 out of 5 average rating, 78 reviews
Top guest favourite
Flat in Saint Michaels
Charming Studio in the heart of St. Michael's, MD.
2 beds, 1 bathroom
12–17 Jul
4.92 out of 5 average rating, 222 reviews
Top guest favourite
Cottage in Leonardtown
Beach Front and 'Perfectly Placed'
2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
4.96 out of 5 average rating, 260 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, 289 reviews
Top guest favourite
Boutique hotel in Oxford
Sandaway Suites & Beach Boutique Hotel, Water View
1 bedroom, 1 king bed, 1 bathroom
21–26 Jul
4.97 out of 5 average rating, 166 reviews
Guest favourite
Hotel room in Oxford
Sandaway Suites & Beach Waterfront Hotel Oxford MD
1 bedroom, 1 king bed, 1 bathroom
21–26 Jul
4.96 out of 5 average rating, 51 reviews
Top guest favourite
Home in Easton
Painted Sky
5 bedrooms, 5 king beds, 4.5 bathrooms
29 Aug – 5 Sept
5.0 out of 5 average rating, 107 reviews
Top guest favourite
Home in Cambridge
Sunset Breezes - quiet waterfront retreat
3 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
4.99 out of 5 average rating, 218 reviews
Guest favourite
Place to stay in Cambridge
Wye Three Oaks
2 bedrooms, 4 beds, 1 bathroom
12–17 Jul
4.96 out of 5 average rating, 93 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