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Search results; Over 1,000 homes in Saint Michaels

Top guest favourite
Home in St. Michaels
Historic Berkeley Hall in the heart of town
2 bedrooms, 2 beds, 1.5 private bathrooms
6–11 Sept
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4.96 out of 5 average rating, 211 reviews
Top guest favourite
Flat in St. Michaels
Blue Crab Lodge
2 bedrooms, 3 beds
16–21 Aug
4.97 out of 5 average rating, 154 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, 308 reviews
Top guest favourite
Flat in St. Michaels
Charming Studio in the heart of St. Michael's, MD.
2 beds
9–14 Aug
4.92 out of 5 average rating, 228 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, 74 reviews
Superhost
Home in St. Michaels
St. Michaels Waterfront Home with Pool
4 bedrooms, 5 beds
1–6 Oct
Top guest favourite
Home in Tilghman Island
The Getaway
3 bedrooms, 3 beds
8–13 Sept
5.0 out of 5 average rating, 28 reviews
Featured hotel
Room in St. Michaels
Standard double room
2 double beds
2–7 Aug
New place to stay
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
4 bedrooms, 6 beds
30 Sept – 5 Oct
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Cottage in St. Michaels
The Little Anchor Cottage, St. Michaels, MD
2 bedrooms, 3 beds
24–29 Aug
4.97 out of 5 average rating, 295 reviews
Top guest favourite
Cottage in St. Michaels
La Casita on Harris Creek, St. Michaels
1 bedroom, 2 beds
6–11 Sept
4.97 out of 5 average rating, 195 reviews
Guest favourite
Home in Tilghman Island
Tilghman Island Retreat By Knapps Narrows!
2 bedrooms, 3 beds
26–31 Aug
4.95 out of 5 average rating, 19 reviews
Top guest favourite
Boutique hotel in Oxford
Hotel Special: Sandaway Suite & Beach - Oxford, MD
1 bedroom, 1 king bed
23–28 Aug
4.94 out of 5 average rating, 63 reviews
Featured hotel
Room in St. Michaels
Standard king room
1 king bed
2–7 Aug
New place to stay
Home in Pasadena
Waterfront Retreat | Pool, Hot Tub & Creek Views
6 bedrooms, 8 beds
24–29 Aug
New place to stay
Top guest favourite
Guest house in Stevensville
Waterfront-View of Bay from your Bed
1 queen bed
20–25 Sept
4.99 out of 5 average rating, 358 reviews
Top guest favourite
Cottage in Easton
Cottage on Solitude Creek, Hot Tub, Pool & Firepit
2 bedrooms, 3 beds
3–8 Nov
5.0 out of 5 average rating, 125 reviews
Guest favourite
Home in Wittman
Eastern Shore Cottage – Near St. Michaels Gateway
3 bedrooms, 3 beds
16–21 Aug
4.93 out of 5 average rating, 15 reviews
Top guest favourite
Home in St. Michaels
Dr. Miller house. Best location-in the heart town
2 bedrooms, 3 beds
30 Aug – 4 Sept
4.92 out of 5 average rating, 220 reviews