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Search results; Over 1,000 homes in Saint Michaels

Top guest favourite
Cottage in Saint Michaels
The Little Anchor Cottage, St. Michaels, MD
2 bedrooms, 3 beds, 1 private bathroom
15–20 Aug
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4.97 out of 5 average rating, 292 reviews
Top guest favourite
Flat in Saint Michaels
Blue Crab Lodge
4.97 out of 5 average rating, 149 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
Top guest favourite
Cottage in Saint Michaels
La Casita on Harris Creek, St. Michaels
4.97 out of 5 average rating, 191 reviews, 1 bedroom, 2 beds, 1 bathroom
28 Jul – 2 Aug
Top guest favourite
Home in Saint Michaels
Shipwrights Cottage in Town!
4.99 out of 5 average rating, 161 reviews, 2 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
5.0 out of 5 average rating, 14 reviews, 4 bedrooms, 6 beds, 3 bathrooms
12–17 Sept
Guest favourite
Houseboat in Cambridge
Loveboat, Where Love Meets The Waves.
5.0 out of 5 average rating, 8 reviews, 1 bedroom, 1 bed, 1 bathroom
25–30 Jul
Top guest favourite
Home in Bozman
The Cottage at Broad Creek
5.0 out of 5 average rating, 40 reviews, 1 bedroom, 1 bed, 1.5 bathrooms
20–25 Jul
Top guest favourite
Home in Cambridge
Relaxing Retreat on the Hudson
4.96 out of 5 average rating, 71 reviews, 5 bedrooms, 5 beds, 2 bathrooms
24–29 Aug
Top guest favourite
Flat in Saint Michaels
Charming Studio in the heart of St. Michael's, MD.
4.92 out of 5 average rating, 223 reviews, 2 beds, 1 bathroom
12–17 Jul
Top guest favourite
Home in Saint Michaels
Private&Cozy/3br+2ba/1mi to town
4.94 out of 5 average rating, 79 reviews, 3 bedrooms, 3 beds, 2 bathrooms
12–17 Jul
Guest favourite
Home in Tilghman Island
Tilghman Island Retreat By Knapps Narrows!
4.94 out of 5 average rating, 17 reviews, 2 bedrooms, 3 beds, 2 bathrooms
10–15 Aug
Top guest favourite
Home in Leonardtown
Water's Edge Cottage | Luxury Retreat
4.99 out of 5 average rating, 132 reviews, 2 bedrooms, 2 beds, 2 bathrooms
2–7 Oct
Guest favourite
Flat in Saint Michaels
Charming Apt. in St. Michaels
4.97 out of 5 average rating, 93 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
26–31 Jul
Top guest favourite
Cottage in Easton
Cottage on Solitude Creek, Hot Tub, Pool & Firepit
5.0 out of 5 average rating, 123 reviews, 2 bedrooms, 3 beds, 2 bathrooms
13–18 Oct
Top guest favourite
Cottage in Leonardtown
Beach Front and 'Perfectly Placed'
4.96 out of 5 average rating, 260 reviews, 2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
Superhost
Room in Saint Michaels
The Snuggery Suites
5.0 out of 5 average rating, 4 reviews, 1 queen bed, 1 bathroom
10–15 Jul
Guest favourite
Hotel room in Oxford
Sandaway Suites & Beach | Town View Eastern Shore
5.0 out of 5 average rating, 22 reviews, 1 bedroom, 1 bed, 1 bathroom
30 Jul – 4 Aug
Guest favourite
Place to stay in Cambridge
Wye Three Oaks
4.96 out of 5 average rating, 95 reviews, 2 bedrooms, 4 beds, 1 bathroom
12–17 Jul
Home in Easton
Sunset's Edge - Family Retreat Near St. Michaels
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
16–21 Jul