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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
1–6 Sept
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4.97 out of 5 average rating, 192 reviews
Top guest favourite
Flat in St. Michaels
Blue Crab Lodge
4.97 out of 5 average rating, 151 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
Superhost
Home in St. Michaels
St. Michaels Waterfront Home with Pool
New place to stay, 4 bedrooms, 5 beds, 4.5 bathrooms
1–6 Oct
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
5.0 out of 5 average rating, 16 reviews, 4 bedrooms, 6 beds, 3 bathrooms
30 Sept – 5 Oct
Top guest favourite
Home in Cambridge
Relaxing Retreat on the Hudson
4.96 out of 5 average rating, 73 reviews, 5 bedrooms, 5 beds, 2 bathrooms
24–29 Aug
Top guest favourite
Boutique hotel in Oxford
Hotel Special: Sandaway Suite & Beach - Oxford, MD
4.94 out of 5 average rating, 63 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
Top guest favourite
Flat in St. Michaels
Charming Studio in the heart of St. Michael's, MD.
4.92 out of 5 average rating, 225 reviews, 2 beds, 1 bathroom
26–31 Jul
Home in Easton
Royal Oak Roadhouse
3 bedrooms, 3 beds, 2.5 bathrooms
19–24 Jul
Guest favourite
Houseboat in Cambridge
Loveboat, Where Love Meets The Waves.
5.0 out of 5 average rating, 9 reviews, 1 bedroom, 1 bed, 1 bathroom
29 Jul – 3 Aug
Guest favourite
Flat in St. Michaels
Charming Apt. in St. Michaels
4.96 out of 5 average rating, 96 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
26–31 Jul
Home in Pasadena
Spacious Family Home in Pasadena
New place to stay, 3 bedrooms, 4 beds, 2.5 bathrooms
26–31 Jul
Guest favourite
Home in Tilghman Island
Tilghman Island Retreat By Knapps Narrows!
4.94 out of 5 average rating, 17 reviews, 2 bedrooms, 3 beds, 2 bathrooms
10–15 Aug
Top guest favourite
Guest house in Stevensville
Waterfront-View of Bay from your Bed
4.99 out of 5 average rating, 353 reviews, 1 bed, 1 bathroom
7–12 Sept
Top guest favourite
Room in St. Michaels
Secluded water - bedroom, sitting room, full bath!
5.0 out of 5 average rating, 38 reviews, 2 single beds, 1 bathroom
10–15 Aug
Guest favourite
Home in St. Michaels
Private&Cozy/3br+2ba/1mi to town
4.94 out of 5 average rating, 80 reviews, 3 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
Guest favourite
Home in Grasonville
Private Waterfront Home W/ Hot Tub, Dock & Kayaks
4.95 out of 5 average rating, 306 reviews, 3 bedrooms, 3 beds, 2 bathrooms
16–21 Aug
Top guest favourite
Cottage in Easton
Cottage on Solitude Creek, Hot Tub, Pool & Firepit
5.0 out of 5 average rating, 124 reviews, 2 bedrooms, 3 beds, 2 bathrooms
25–30 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
Home in Leonardtown
Water's Edge Cottage | Luxury Retreat
4.99 out of 5 average rating, 135 reviews, 2 bedrooms, 2 beds, 2 bathrooms
2–7 Oct