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Vacation rentals in Saint Michaels

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Top-rated vacation rentals in Saint Michaels

Guests agree: these stays are highly rated for location, cleanliness, and more.

The Little Anchor Cottage, St. Michaels, MD
SUPERHOST
Entire cottage · 4 guests · 3 beds · 1 bath

The Little Anchor Cottage, St. Michaels, MDWelcome to the Little Anchor cottage in St. Michaels, Maryland! The cottage was built in late 1880s and is located in the charming Historic District, where you can enjoy the convenience of walking one block to the downtown shops and restaurants on S. Talbot street. And for another 5 to 15 minute walk, you can reach more waterfront dining on St. Michaels Harbor with its boat slips, boat ramps, the Chesapeake Bay Maritime Museum, Muskrat Park and Hollis Park.

St. Michaels-Historic Dist.  Margaret Wells House
SUPERHOST
Entire cottage · 4 guests · 2 beds · 2 baths

St. Michaels-Historic Dist. Margaret Wells HouseThe Margaret Wells House is in the heart of the Historic District between the main street and water. Enjoy a total renovation of this charming home. A short walk to the water's edge, Inn at Perry Cabin, Chesapeake Bay Maritime Museum, restaurants, shops, winery, brewery and local market. A perfect spot for a couple's Shore weekend getaway or attending a wedding, nearby. Our nightly pricing includes coffee, tea, fresh linens on beds, hand-milled natural soap, fresh bath towels and wash cloths.

La Casita on Harris Creek, St. Michaels
SUPERHOST
Entire cottage · 3 guests · 2 beds · 1 bath

La Casita on Harris Creek, St. MichaelsNewly constructed architecturally unique guesthouse inspired by the historic barns of the Chesapeake. Stay in luxury on a secluded 40 acre farm on Harris Creek, be at one w/nature & still be close enough to enjoy the fine dining, shops & charm that is St Michaels. 5 minutes from town, 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020

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Popular amenities for Saint Michaels vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

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Saint Michaels downtown! Walk to everything!!
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Historic Berkeley Hall in the heart of town
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Dr. Miller house. Best location-in the heart town
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Furnished Cottage...Best place!
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Gorgeous Cottage: Easy Walk into St Michaels Town!
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Small Historic House Downtown St Michaels
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Walk to Everything House
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Miles Aweigh

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