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Vacation rentals in Saint Michaels

Vacation rentals in Saint Michaels

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Saint Michaels

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

  • St. Michaels-Historic Dist.  Margaret Wells House
    SUPERHOSTEntire cottage · 4 guests · 2 beds · 2 bathrooms
    St. Michaels-Historic Dist. Margaret Wells House

    The 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.

    What guests are saying:

    “My friends and I got the privilege to spend a girls weekend in Missy’s beautiful historical home. The location was fantastic.....we parked the car and walked everywhere. Close to quaint little boutiques and fabulous restaurants. Missy was so thoughtful to suggest places to eat for dinner and added a brief description of each place. Which was very helpful for our planning. Her home was absolutely sparkling upon arriving. So clean.....beautifully and tastefully decorated. Checking in and out was so easy. I’m already planning a future trip back to Saint Michael’s with my husband and I know exactly where we will be staying......at Missy’s. Thank you Missy”

  • Miles Aweigh
    SUPERHOSTEntire house · 6 guests · 4 beds · 2 bathrooms
    Miles Aweigh

    Our cottage is less than a mile from St. Michaels town center. Restaurants, shopping, Chesapeake Maritime Museum, Easton-Tilghman Island. Bike, walk or drive...our home has been recently updated with new furnishings throughout!

    What guests are saying:

    “I cannot say enough good things about this property, as well as Michele and Chris. The house and property were immaculate, we felt extremely comfortable there, and the owners were very hospitable. We enjoyed the many areas to sit outside, and the house was very cozy. Had all the amenities we could need! It's only a mile from the heart of St. Michaels, which was very convenient. We hope to be back next year!”

  • Spacious apartment, private entrance - water views
    SUPERHOSTEntire house · 2 guests · 1 bed · 1 bathroom
    Spacious apartment, private entrance - water views

    We want you to be as comfortable as we would want to be if we were staying here for business or pleasure. 20 minutes from Annapolis, private apartment, separate entrance, parking, queen comfort bed, kitchenette, WIFI --professional work space. Amenities include a breakfast basket with homemade treats and special surprises. Discount for weekly or monthly rentals and returning guests. Includes an onsite "Uber" driver. Near Old Stein Inn & stores. Perfect for "overflow" guests & academy parents.

    What guests are saying:

    “My son and I stayed here while he competed in a lacrosse showcase in the area. Linda and her place- absolutely wonderful! The place was perfect and comfortable. We appreciated the thoughtful touches like the snacks & drinks and coffee for the morning. Linda made this a very pleasant stay. I hope to stay at her place again if we are in the area in the future.”

Holiday rentals for every style

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Popular amenities for Saint Michaels holiday rentals

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

Other great holiday rentals in Saint Michaels

Quiet and welcoming
SUPERHOSTPrivate room
Quiet and welcoming
Price:£52 / night
"Happy Campers" Waterfront Apartment!
SUPERHOSTEntire guest house
"Happy Campers" Waterfront Apartment!
Price:£119 / night
Sailwinds Loft at Cambridge Creek
SUPERHOSTEntire guest suite
Sailwinds Loft at Cambridge Creek
Price:£75 / night
New Hotel Chic
SUPERHOSTEntire house
New Hotel Chic
Price:£111 / night
Wall to Wall Cool- Filled with Original Art and Sculpture
PlusEntire flat
Wall to Wall Cool- Filled with Original Art and Sculpture
Price:£80 / night
Boutique by the Bay
SUPERHOSTEntire flat
Boutique by the Bay
Price:£139 / night
Gorgeous Cottage: Easy Walk into St Michaels Town!
Entire guest suite
Gorgeous Cottage: Easy Walk into St Michaels Town!
Price:£31 / night
Bartlett Pear Inn, Green Anjou Suite
Room in boutique hotel
Bartlett Pear Inn, Green Anjou Suite
Price:£100 / night
Waterfront Cottage Near St. Michaels and Easton
SUPERHOSTEntire house
Waterfront Cottage Near St. Michaels and Easton
Price:£199 / night
Quiet Country Getaway
SUPERHOSTPrivate room
Quiet Country Getaway
Price:£119 / night
Bartlett Pear Inn, Forelle Suite
Room in boutique hotel
Bartlett Pear Inn, Forelle Suite
Price:£115 / night
Wye River Cottage and Horse Barn
SUPERHOSTEntire cottage
Wye River Cottage and Horse Barn
Price:£107 / night
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