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Search results; Over 1,000 homes in Saint Michaels

Top guest favourite
Home in St. Michaels
Shipwrights Cottage in Town!
2 bedrooms, 3 beds, 2 bathrooms
11–16 Oct
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4.99 out of 5 average rating, 172 reviews
Top guest favourite
Flat in St. Michaels
Blue Crab Lodge
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 158 reviews
Top guest favourite
Home in St. Michaels
Miles Aweigh
3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
4.97 out of 5 average rating, 299 reviews
Top guest favourite
Home in St. Michaels
Private&Cozy/3br+2ba/1mi to town
3 bedrooms, 3 beds, 2 bathrooms
25–30 Oct
4.94 out of 5 average rating, 87 reviews
Superhost
Home in St. Michaels
St. Michaels Waterfront Home with Pool
4 bedrooms, 5 beds, 4.5 bathrooms
1–6 Oct
Guest favourite
Flat in St. Michaels
Downtown St. Michaels | Porch + Pet-Friendly
3 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 25 reviews
Top guest favourite
Home in St. Michaels
Ahoy St. Michaels! - A Historic Retreat
2 bedrooms, 3 beds, 2.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 58 reviews
Home in Easton
Royal Oak Roadhouse
3 bedrooms, 3 beds, 2.5 bathrooms
27 Sept – 2 Oct
Top guest favourite
Home in Easton
4 bdrm, 3 bath, 2,700 sqft whole house on 1 acre
4 bedrooms, 4 beds, 3 bathrooms
1–6 Sept
4.97 out of 5 average rating, 99 reviews
Top guest favourite
Cottage in St. Michaels
The Little Anchor Cottage, St. Michaels, MD
2 bedrooms, 3 beds, 1 bathroom
4–9 Oct
4.97 out of 5 average rating, 299 reviews
Guest favourite
Home in Easton
St. Michaels Waterfront Home with Private Dock
3 bedrooms, 6 beds, 2.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Home in Cambridge
Relaxing Retreat on the Hudson
5 bedrooms, 5 beds, 2 bathrooms
4–9 Oct
4.96 out of 5 average rating, 78 reviews
Top guest favourite
Home in St. Michaels
Grace Cottage, Saint Michaels Walk to everything!
2 bedrooms, 2 king beds, 2.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 15 reviews
Guest favourite
Cabin in St. Michaels
True St. Michaels 6 Acre Waterfront w/heated pool
5 bedrooms, 11 beds, 3 bathrooms
7–12 Sept
4.99 out of 5 average rating, 124 reviews
Guest favourite
Room in St. Michaels
The Snuggery Inn & Suites
1 queen bed, 1 bathroom
1–6 Sept
4.86 out of 5 average rating, 7 reviews
Top guest favourite
Home in Easton
Newly Renovated Modern Waterfront Home
5 bedrooms, 13 beds, 5.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 42 reviews
Top guest favourite
Home in St. Michaels
Historic Berkeley Hall in the heart of town
2 bedrooms, 2 beds, 1.5 bathrooms
8–13 Sept
4.96 out of 5 average rating, 216 reviews
Top guest favourite
Home in Easton
Eastern Shore Retreat!
3 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 56 reviews
Featured hotel
Room in St. Michaels
Standard queen room
1 queen bed, 1 bathroom
6–11 Sept
New place to stay