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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, 193 reviews
Top guest favourite
Cottage in St. Michaels
The Little Anchor Cottage, St. Michaels, MD
4.97 out of 5 average rating, 293 reviews, 2 bedrooms, 3 beds, 1 bathroom
15–20 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
Room in St. Michaels
Secluded water - bedroom, sitting room, full bath!
5.0 out of 5 average rating, 39 reviews, 2 single beds, 1 bathroom
10–15 Aug
Top guest favourite
Home in Easton
Eastern Shore Retreat!
5.0 out of 5 average rating, 53 reviews, 3 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
Home in Bozman
Brand-New Pool! Waterfront Bozman Village Home
4.85 out of 5 average rating, 13 reviews, 4 bedrooms, 6 beds, 2.5 bathrooms
4–9 Oct
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
Superhost
Home in Royal Oak
Waterfront Family Retreat - mins from St. Michaels
5.0 out of 5 average rating, 3 reviews, 6 bedrooms, 9 beds, 4.5 bathrooms
30 Aug – 4 Sept
Guest favourite
Home in Newcomb
Saint Michaels Waterfront Home
4.99 out of 5 average rating, 67 reviews, 2 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
Top guest favourite
Home in Oxford
Stunning Chesapeake waterfront home
4.99 out of 5 average rating, 93 reviews, 5 bedrooms, 9 beds, 4.5 bathrooms
2–7 Aug
Top guest favourite
Home in St. Michaels
Grace Cottage, Saint Michaels Walk to everything!
5.0 out of 5 average rating, 11 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
2–7 Aug
Top guest favourite
Room in Cambridge
Waterfront Room at Happy Campers
5.0 out of 5 average rating, 61 reviews, 1 queen bed, 1 bathroom
24–29 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, 226 reviews, 2 beds, 1 bathroom
9–14 Aug
Top guest favourite
Flat in St. Michaels
Blue Crab Lodge
4.97 out of 5 average rating, 152 reviews, 2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
Top guest favourite
Home in St. Michaels
Shipwrights Cottage in Town!
4.99 out of 5 average rating, 163 reviews, 2 bedrooms, 3 beds, 2 bathrooms
16–21 Aug
Top guest favourite
Home in St. Michaels
Ahoy St. Michaels! - A Historic Retreat
5.0 out of 5 average rating, 51 reviews, 2 bedrooms, 3 beds, 2.5 bathrooms
2–7 Aug
Top guest favourite
Home in Leonardtown
Water's Edge Cottage | Luxury Retreat
4.99 out of 5 average rating, 134 reviews, 2 bedrooms, 2 beds, 2 bathrooms
2–7 Oct
Guest favourite
Home in St. Michaels
Private&Cozy/3br+2ba/1mi to town
4.94 out of 5 average rating, 81 reviews, 3 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Home in St. Michaels
Historic Berkeley Hall in the heart of town
4.96 out of 5 average rating, 210 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
30 Aug – 4 Sept