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Search results; Over 1,000 homes in Saint Michaels

Top guest favourite
Home in St. Michaels
Small Historic House Downtown St Michaels
1 bedroom, 1 bed, 1 private bathroom
26–31 Oct
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4.89 out of 5 average rating, 236 reviews
Top guest favourite
Flat in St. Michaels
Blue Crab Lodge
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 158 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, 299 reviews
Superhost
Home in Stevensville
Private & Peaceful | Water Views, Big Deck, Games
3 bedrooms, 5 beds, 3 bathrooms
13–18 Sept
New place to stay
Top guest favourite
Flat in St. Michaels
Charming Studio in the heart of St. Michael's, MD.
2 beds, 1 bathroom
20–25 Sept
4.92 out of 5 average rating, 230 reviews
Top guest favourite
Boutique hotel in Oxford
Sandaway Suites & Beach Boutique Hotel, Water View
1 bedroom, 1 king bed, 1 bathroom
9–14 Sept
4.97 out of 5 average rating, 169 reviews
Home in Easton
Royal Oak Roadhouse
3 bedrooms, 3 beds, 2.5 bathrooms
27 Sept – 2 Oct
Featured hotel
Room in St. Michaels
Standard queen room
1 queen bed, 1 bathroom
6–11 Sept
New place to stay
Guest favourite
Hotel room in Oxford
Sandaway Suites & Beach Waterfront Hotel Oxford MD
1 bedroom, 1 king bed, 1 bathroom
9–14 Sept
4.95 out of 5 average rating, 60 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, 24 reviews
Top guest favourite
Home in St. Michaels
Historic Berkeley Hall in the heart of town
2 bedrooms, 2 beds, 1.5 bathrooms
8–13 Sept
4.96 out of 5 average rating, 215 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, 139 reviews
Top guest favourite
Home in Easton
Arcadia Shores On The Cove
4 bedrooms, 7 beds, 4 bathrooms
1–6 Sept
4.94 out of 5 average rating, 18 reviews
Guest favourite
Home in Grasonville
Private Waterfront Home W/ Hot Tub, Dock & Kayaks
3 bedrooms, 3 queen beds, 2 bathrooms
13–18 Sept
4.95 out of 5 average rating, 308 reviews
Top 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, 86 reviews
Top guest favourite
Home in Bozman
The Cottage at Broad Creek
1 bedroom, 1 bed, 1.5 bathrooms
11–16 Sept
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Home in St. Michaels
Ahoy St. Michaels! - A Historic Retreat
2 bedrooms, 3 beds, 2.5 bathrooms
3–8 Sept
5.0 out of 5 average rating, 57 reviews
Guest favourite
Home in Sherwood
Punch Point boasts a sandy beach w/ pool and pier
5 bedrooms, 5 beds, 4.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Home in St. Michaels
Dr. Miller house. Best location-in the heart town
2 bedrooms, 3 beds, 1.5 bathrooms
20–25 Sept
4.92 out of 5 average rating, 224 reviews