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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
2 bedrooms, 3 beds
19–24 Jul
4.97 out of 5 average rating, 151 reviews
Superhost
Home in St. Michaels
St. Michaels Waterfront Home with Pool
4 bedrooms, 5 beds
1–6 Oct
New place to stay
Top guest favourite
Boutique hotel in Oxford
Hotel Special: Sandaway Suite & Beach - Oxford, MD
1 bedroom, 1 king bed
2–7 Aug
4.94 out of 5 average rating, 63 reviews
Top guest favourite
Home in Cambridge
Relaxing Retreat on the Hudson
5 bedrooms, 5 beds
24–29 Aug
4.96 out of 5 average rating, 73 reviews
Home in Easton
Royal Oak Roadhouse
3 bedrooms, 3 beds
19–24 Jul
Guest favourite
Houseboat in Cambridge
Loveboat, Where Love Meets The Waves.
1 bedroom, 1 bed
29 Jul – 3 Aug
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Flat in St. Michaels
Charming Studio in the heart of St. Michael's, MD.
2 beds
26–31 Jul
4.92 out of 5 average rating, 225 reviews
Home in Pasadena
Spacious Family Home in Pasadena
3 bedrooms, 4 beds
26–31 Jul
New place to stay
Guest favourite
Flat in St. Michaels
Charming Apt. in St. Michaels
1 bedroom, 2 beds
26–31 Jul
4.96 out of 5 average rating, 96 reviews
Top guest favourite
Guest house in Stevensville
Waterfront-View of Bay from your Bed
1 queen bed
7–12 Sept
4.99 out of 5 average rating, 353 reviews
Top guest favourite
Room in St. Michaels
Secluded water - bedroom, sitting room, full bath!
2 single beds
10–15 Aug
5.0 out of 5 average rating, 38 reviews
Guest favourite
Home in Grasonville
Private Waterfront Home W/ Hot Tub, Dock & Kayaks
3 bedrooms, 3 queen beds
16–21 Aug
4.95 out of 5 average rating, 306 reviews
Guest favourite
Home in Tilghman Island
Tilghman Island Retreat By Knapps Narrows!
2 bedrooms, 3 beds
10–15 Aug
4.94 out of 5 average rating, 18 reviews
Top guest favourite
Cottage in Easton
Cottage on Solitude Creek, Hot Tub, Pool & Firepit
2 bedrooms, 3 beds
25–30 Aug
5.0 out of 5 average rating, 124 reviews
Guest favourite
Home in St. Michaels
Private&Cozy/3br+2ba/1mi to town
3 bedrooms, 3 beds
9–14 Aug
4.94 out of 5 average rating, 80 reviews
Top guest favourite
Home in Cambridge
Sunset Breezes - quiet waterfront retreat
3 bedrooms, 5 beds
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
25–30 Jul
4.96 out of 5 average rating, 96 reviews
Top guest favourite
Home in Leonardtown
Water's Edge Cottage | Luxury Retreat
2 bedrooms, 2 beds
2–7 Oct
4.99 out of 5 average rating, 135 reviews