Skip to content

Vacation rentals in Saint Michaels

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Saint Michaels

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

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 with nature & still only 5 min from town's fine dining, shops & charm . With 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, washer/drier, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020.
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.

Vacation rentals for every style

Get the amount of space that is right for you

  • Homes
  • Hotels
  • Unique stays

Other great vacation rentals in Saint Michaels

SUPERHOST
  1. Entire residential home
  2. Saint Michaels
Carpenter St. Cottage In Town St. Michaels!
$267 per night
SUPERHOST
  1. Entire residential home
  2. Saint Michaels
The Dollhouse in Central Historic St Michaels
$200 per night
SUPERHOST
  1. Entire residential home
  2. Saint Michaels
Dr. Miller house. Best location-in the heart town
$246 per night
SUPERHOST
  1. Entire residential home
  2. Saint Michaels
Grace Cottage, Saint Michaels Walk to everything!
$555 per night
SUPERHOST
  1. Entire residential home
  2. Saint Michaels
Walk to Everything House
$225 per night
SUPERHOST
  1. Entire guest suite
  2. Saint Michaels
Charming Studio in the heart of St. Michael's, MD.
$282 per night
SUPERHOST
  1. Entire residential home
  2. Saint Michaels
Harrison House - in Town and on St Michaels Harbor
$416 per night
SUPERHOST
  1. Entire residential home
  2. Saint Michaels
Historic Berkeley Hall in the heart of town
$296 per night
SUPERHOST
  1. Entire residential home
  2. Saint Michaels
Saint Michael's Premier Rental -Heated Pool
$211 per night
SUPERHOST
  1. Entire residential home
  2. Saint Michaels
TRUE ST MICHAELS 6 ACRE WATERFRONT!!!
$465 per night
  1. Entire residential home
  2. St. Michaels
Crabber's Cove - Charming Waterfront Near St. Michaels, Kayaks & Bikes!
$470 per night
SUPERHOST
  1. Entire residential home
  2. Saint Michaels
Miles Aweigh
$375 per night