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Search results; Over 1,000 homes in Saint Michaels

Guest favorite
Home in St. Michaels
Restored 1850s home, walk to everything
2 bedrooms, 4 beds, 1.5 baths
Aug 16 – 21
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4.87 out of 5 average rating, 141 reviews
Top guest favorite
Apartment in St. Michaels
Above a coffee shop in downtown St. Michaels
4.97 out of 5 average rating, 157 reviews, 2 bedrooms, 3 beds, 1 bath
Aug 16 – 21
Top guest favorite
Home in St. Michaels
Historic shipwright’s cottage with a balcony
4.99 out of 5 average rating, 169 reviews, 2 bedrooms, 3 beds, 2 baths
Aug 16 – 21
Guest favorite
Home in Grasonville
Waterfront home with a dock and hot tub
4.95 out of 5 average rating, 308 reviews, 3 bedrooms, 3 beds, 2 baths
Aug 16 – 21
Top guest favorite
Apartment in St. Michaels
Historic 1850s building on Talbot Street
4.92 out of 5 average rating, 229 reviews, 2 beds, 1 bath
Aug 16 – 21
Top guest favorite
Home in St. Michaels
Creek-view cottage with pool, near town
4.97 out of 5 average rating, 297 reviews, 3 bedrooms, 4 beds, 2 baths
Sep 28 – Oct 3
Top guest favorite
Home in Tilghman Island
Island home with a fire pit and hammock
5.0 out of 5 average rating, 31 reviews, 3 bedrooms, 3 beds, 2 baths
Sep 8 – 13
Top guest favorite
Cottage in St. Michaels
1880s cottage one block from downtown
4.97 out of 5 average rating, 297 reviews, 2 bedrooms, 3 beds, 1 bath
Aug 24 – 29
Home in Bozman
Waterfront with a dock, pool, and hot tub
4.8 out of 5 average rating, 15 reviews, 4 bedrooms, 6 beds, 2.5 baths
Oct 4 – 9
Top guest favorite
Home in Leonardtown
Waterfront cottage with Potomac River views
4.99 out of 5 average rating, 137 reviews, 2 bedrooms, 2 beds, 2 baths
Oct 26 – 31
Top guest favorite
Home in St. Michaels
Historic 1840s home, 3 blocks to water
4.96 out of 5 average rating, 212 reviews, 2 bedrooms, 2 beds, 1.5 baths
Sep 6 – 11
Top guest favorite
Home in St. Michaels
Historic duplex 3 blocks from water
4.92 out of 5 average rating, 223 reviews, 2 bedrooms, 3 beds, 1.5 baths
Aug 30 – Sep 4
Top guest favorite
Cottage in Wittman
Waterfront with kayaks, dock, and sunsets
4.9 out of 5 average rating, 198 reviews, 3 bedrooms, 3 beds, 2 baths
Oct 27 – Nov 1
Guest favorite
Apartment in St. Michaels
British-themed flat in an 1850s building
4.96 out of 5 average rating, 98 reviews, 1 bedroom, 2 beds, 1.5 baths
Aug 16 – 21
Top guest favorite
Home in Stevensville
Waterfront with swim spa, sauna, and dock
5.0 out of 5 average rating, 22 reviews, 4 bedrooms, 6 beds, 3 baths
Sep 30 – Oct 5
Top guest favorite
Home in Tilghman Island
Waterfront cottage with panoramic harbor views
4.95 out of 5 average rating, 43 reviews, 2 bedrooms, 2 beds, 1 bath
Aug 29 – Sep 3
Superhost
Home in St. Michaels
New waterfront home with a private pool
4 bedrooms, 5 beds, 4.5 baths
Oct 1 – 6
Top guest favorite
Hotel room in Oxford
Private beach on a 19th-century estate
4.95 out of 5 average rating, 59 reviews, 1 bedroom, 1 bed, 1 bath
Aug 23 – 28
Guest favorite
Home in Easton
Gated carriage house on 80 acres
4.85 out of 5 average rating, 163 reviews, 5 bedrooms, 7 beds, 2 baths
Aug 13 – 18