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Search results; Over 1,000 homes in Saint Michaels

Top guest favourite
Home in St. 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, 113 reviews
Top guest favourite
Flat in St. Michaels
Blue Crab Lodge
4.97 out of 5 average rating, 154 reviews, 2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
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
Cottage in St. Michaels
La Casita on Harris Creek, St. Michaels
4.97 out of 5 average rating, 194 reviews, 1 bedroom, 2 beds, 1 bathroom
6–11 Sept
Top guest favourite
Flat in St. Michaels
Charming Studio in the heart of St. Michael's, MD.
4.92 out of 5 average rating, 227 reviews, 2 beds, 1 bathroom
9–14 Aug
Featured hotel
Room in St. Michaels
Standard double room
New place to stay, 2 double beds, 1 bathroom
2–7 Aug
Guest favourite
Home in Grasonville
Private Waterfront Home W/ Hot Tub, Dock & Kayaks
4.95 out of 5 average rating, 307 reviews, 3 bedrooms, 3 beds, 2 bathrooms
16–21 Aug
Top guest favourite
Cottage in St. Michaels
The Little Anchor Cottage, St. Michaels, MD
4.97 out of 5 average rating, 295 reviews, 2 bedrooms, 3 beds, 1 bathroom
24–29 Aug
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
5.0 out of 5 average rating, 19 reviews, 4 bedrooms, 6 beds, 3 bathrooms
30 Sept – 5 Oct
Guest favourite
Home in St. Michaels
Private&Cozy/3br+2ba/1mi to town
4.94 out of 5 average rating, 83 reviews, 3 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Home in Tilghman Island
The Getaway
5.0 out of 5 average rating, 28 reviews, 3 bedrooms, 3 beds, 2 bathrooms
8–13 Sept
Featured hotel
Room in St. Michaels
Standard king room
New place to stay, 1 king bed, 1 bathroom
1–6 Aug
Top guest favourite
Home in Easton
Painted Sky
5.0 out of 5 average rating, 111 reviews, 5 bedrooms, 8 beds, 4.5 bathrooms
29 Aug – 5 Sept
Top guest favourite
Cottage in Easton
Cottage on Solitude Creek, Hot Tub, Pool & Firepit
5.0 out of 5 average rating, 125 reviews, 2 bedrooms, 3 beds, 2 bathrooms
3–8 Nov
Guest favourite
Flat in St. Michaels
Charming Apt. in St. Michaels
4.96 out of 5 average rating, 97 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
9–14 Aug
Top guest favourite
Cottage in Wittman
"Wittman Cottage"
4.9 out of 5 average rating, 197 reviews, 3 bedrooms, 3 beds, 2 bathrooms
27 Oct – 1 Nov
Top guest favourite
Home in St. Michaels
Margaret Wells House
4.98 out of 5 average rating, 46 reviews, 2 bedrooms, 2 beds, 2 bathrooms
13–18 Sept
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
Home in Easton
Royal Oak Roadhouse
3 bedrooms, 3 beds, 2.5 bathrooms
30 Aug – 4 Sept