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Hotels in St. Michaels

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Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln, St. Michaels, MD
  • 13 min walk from St. Michaels Winery
Book a stay at this luxury hotel in St. Michaels. Enjoy free WiFi, free valet parking, and a full-service spa. Our guests praise the helpful staff in our reviews. ...
9.4/10 Exceptional! (355 reviews)
"The setting is spectacular and the staff could not have been kinder and more helpful."

Reviewed on Jul 13, 2025

Inn at Perry Cabin
The Wildset

The Wildset

2.5 out of 5
209 N Talbot St, St. Michaels, MD
  • 10 min walk from St. Michaels Winery
Stay at this hotel in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
9.6/10 Exceptional! (346 reviews)
"Site was exactly as advertised. The team was very responsive, and the service at breakfast wonderful. My only complaint would be the excessive (in my opinion) property lighting all through the night."

Reviewed on Jul 31, 2025

The Wildset
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
  • 19 min walk from St. Michaels Winery
Book a stay at this business-friendly hotel in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8/10 Very Good! (1,003 reviews)
"We had a great time during our visit. Pool could use more seating and umbrellas. Rooms a bit dated. Overall, great time and would return. Great value for your money"

Reviewed on Jul 31, 2025

St Michaels Inn
Parsonage Inn

Parsonage Inn

3.5 out of 5
210 North Talbot Street, St. Michaels, MD
  • 12 min walk from St. Michaels Winery
Stay at this 3.5-star B&B in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Perry Cabin Park and Higgins Yacht Yard and ...
9.2/10 Wonderful! (129 reviews)
"Beautiful Victorian Cottage Home. Outstanding service and breakfast. Wonderful hosts made us feel right @ home!"

Reviewed on Apr 18, 2025

Parsonage Inn
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle, Annapolis, MD
  • 37 min drive from St. Michaels Winery
Book a stay at this historic hotel in Annapolis. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,813 reviews)
"Enjoyed the stay! Beautiful place!"

Reviewed on Jul 28, 2025

Historic Inns of Annapolis
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St, Annapolis, MD
  • 37 min drive from St. Michaels Winery
Stay at this 4-star business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and ...
9.2/10 Wonderful! (1,000 reviews)
First class
"It was pouring when we arrived, my wife and i were soaked and the staff was at the front desk with warm towels. Beginning to end first class service, attentiveness and respectful."

Reviewed on Jul 28, 2025

Graduate by Hilton Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court, Annapolis, MD
  • 39 min drive from St. Michaels Winery
Stay at this 4-star business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the ...
8.4/10 Very Good! (1,005 reviews)
Great place to stay
"The suite was very comfortable and open. The bed was very nice and comfortable. From the time we entered the main lobby we were made very welcoming. There's one restaurant at the hotel that provides you with a good variety of food. The bartender (Carlos) is from the area and recommended several places ..."

Reviewed on Aug 1, 2025

DoubleTree by Hilton Hotel Annapolis
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

3 out of 5
2600 Housley Road, Annapolis, MD
  • 40 min drive from St. Michaels Winery
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (1,002 reviews)
"Just stayed overnight but what a nice room! Like a small apartment."

Reviewed on Jul 30, 2025

Country Inn & Suites by Radisson, Annapolis, MD
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4 out of 5
80 Compromise St, Annapolis, MD
  • 36 min drive from St. Michaels Winery
Stay at this 4-star eco-certified hotel in Annapolis. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.8/10 Excellent! (848 reviews)
"We were pleased with the staff, room and the view. We were disappointed that there was no restaurant or bar on the property as the description led us to believe."

Reviewed on Jul 31, 2025

Annapolis Waterfront Hotel, Autograph Collection
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

3 out of 5
174 West Street, Annapolis, MD
  • 37 min drive from St. Michaels Winery
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
8.4/10 Very Good! (1,000 reviews)
"Great location"

Reviewed on Jul 28, 2025

Hilton Garden Inn Annapolis Downtown
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd, Annapolis, MD
  • 40 min drive from St. Michaels Winery
Stay at this 3.5-star business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.6/10 Excellent! (1,003 reviews)
Nice hotel, but elevators are slow!
"It was a very short stop on our way to vacation. Check-in went fine, quick and efficient. Unfortunately one of room keys did not work, so I had to head back down to get it re-programmed. This happens often, so it is not knock on the hotel. The elevators, however, are the slowest I have ever encountered ..."

Reviewed on Jul 24, 2025

Crowne Plaza Annapolis by IHG
SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

3 out of 5
189 Admiral Cochrane Drive, Annapolis, MD
  • 38 min drive from St. Michaels Winery
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and ...
9/10 Wonderful! (1,002 reviews)
"Good breakfast included. Laundry worked perfectly and close enough to DC and Annapoli"

Reviewed on Jul 31, 2025

SpringHill Suites by Marriott Annapolis
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.

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