St. Michaels Vacation Rentals
Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Vacation Rentals in St. Michaels
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, 106 reviews
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, 109 reviews
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, 27 reviews
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, 5 reviews
Cozy place close to the city dock
Cozy place close to the city dock
10.0 out of 10, Exceptional, 55 reviews
Pool and Bay Views on wrap around deck in Kent Island
Pool and Bay Views on wrap around deck in Kent Island
9.6 out of 10, Exceptional, 21 reviews
Directly Across from Gate One & Steps from the Waterfront
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, 182 reviews
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
9.8 out of 10, Exceptional, 15 reviews
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, 187 reviews
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
9.6 out of 10, Exceptional, 5 reviews
Firefly Cottage at the Cape, community beach, stand alone house, hot tub, pets.
Firefly Cottage at the Cape, community beach, stand alone house, hot tub, pets.
10.0 out of 10, Exceptional, 62 reviews
Recently Renovated Annapolis Home - Conveniently Located
Recently Renovated Annapolis Home - Conveniently Located
10.0 out of 10, Exceptional, 44 reviews
Chesapeake Houseboat Getaway on Kent Island, Maryland
Chesapeake Houseboat Getaway on Kent Island, Maryland
10.0 out of 10, Exceptional, 8 reviews
Waterfront Cottage on the Eastern Shore
Waterfront Cottage on the Eastern Shore
9.4 out of 10, Exceptional, 3 reviews
The price is ¥94,283
per night
Jun 18 - Jun 19
Charming Annapolis WaterVIEW Home
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, 43 reviews
The price is ¥62,803
per night
Jul 10 - Jul 11
Relax on Kent Island in 3 Bedroom Home w/Waterview
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, 19 reviews
The price is ¥22,973
per night
Jun 26 - Jun 27
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
10.0 out of 10, Exceptional, 28 reviews
Gorgeous dog-friendly retreat w/ fireplace, patio, & firepit - centrally located
Gorgeous dog-friendly retreat w/ fireplace, patio, & firepit - centrally located
10.0 out of 10, Exceptional, 6 reviews
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
10.0 out of 10, Exceptional, 25 reviews
Indulge or be still near Naval Academy/ Annapolis
Indulge or be still near Naval Academy/ Annapolis
9.2 out of 10, Wonderful, 9 reviews
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Other types of properties in St. Michaels you may be interested in
The price is ¥23,610
per night
Jul 7 - Jul 8
The price is ¥117,578
per night
Jun 19 - Jun 20
The price is ¥43,915
per night
Jul 1 - Jul 2
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Search for holiday rentals in St. Michaels on Expedia! You can easily find your home rentals, villas, holiday apartments in St. Michaels using one of the methods below:
- View our selection of featured holiday rentals in St. Michaels
- Use the map to find apartments and other holiday homes in the St. Michaels neighbourhood you prefer
- Enter your travel dates to view the best deals on holiday rentals in St. Michaels while they last
Look no further and take a look at our great range of rental properties in St. Michaels!
Frequently asked questions
Recent reviews of St. Michaels propertiesExpedia verified reviews
![Hilton Garden Inn Annapolis](http://images.trvl-media.com/lodging/2000000/1650000/1641200/1641168/f7bcd5fc_y.jpg)
Hilton Garden Inn Annapolis
5/5 Excellent
"Good"
A verified traveler stayed at Hilton Garden Inn Annapolis
Posted 17 hours ago