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Search results; Over 1,000 homes in Saint Michaels

Top guest favourite
Home in Saint 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, 112 reviews
Top guest favourite
Flat in Saint Michaels
Blue Crab Lodge
4.97 out of 5 average rating, 150 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
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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
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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
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
Boutique hotel in Oxford
Sandaway Suites & Beach Boutique Hotel, Water View
4.97 out of 5 average rating, 167 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 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
Home in Easton
Royal Oak Roadhouse
3 bedrooms, 3 beds, 2.5 bathrooms
19–24 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
27 Jul – 1 Aug
Top 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
26–31 Jul
Top guest favourite
Flat in Saint Michaels
Charming Studio in the heart of St. Michael's, MD.
4.92 out of 5 average rating, 224 reviews, 2 beds, 1 bathroom
14–19 Jul
Guest favourite
Flat in Saint Michaels
Charming Apt. in St. Michaels
4.96 out of 5 average rating, 95 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
26–31 Jul
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
30 Aug – 4 Sept
Top guest favourite
Home in Bozman
The Cottage at Broad Creek
5.0 out of 5 average rating, 41 reviews, 1 bedroom, 1 bed, 1.5 bathrooms
20–25 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 Cambridge
Sunset Breezes - quiet waterfront retreat
4.99 out of 5 average rating, 218 reviews, 3 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
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Home in Saint Michaels
Miles Aweigh
4.97 out of 5 average rating, 290 reviews, 3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
Top 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
24–29 Jul
Top guest favourite
Home in Easton
Arcadia Shores On The Cove
5.0 out of 5 average rating, 15 reviews, 4 bedrooms, 7 beds, 4 bathrooms
13–18 Sept