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Hotels in St. Michaels

Choose from 1282 St. Michaels Hotel Deals

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! (1,004 reviews)
"We enjoyed our 3 day stay at St Michaels inn everyone was friendly and the free breakfast was good"

Reviewed on Jun 28, 2025

St Michaels Inn
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! (350 reviews)
Cool place but very pricey
"Fabulous place on the water. Nice pool, beautiful gardens, beautiful common areas. It seems a fair bit over priced though. We stayed for two weeknights and with the taxes, fees (and of course a $65 “resort fee” (haven’t they been banned yet) each night was pushing $800. The room was average size, ..."

Reviewed on Jun 27, 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! (329 reviews)
"Very nice place. The in house resturant was very good. Good location to sites. easy walk to most things."

Reviewed on Jun 27, 2025

The Wildset
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! (1,789 reviews)
"Perfect for those that love American history"

Reviewed on Jun 29, 2025

Historic Inns of 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! (1,003 reviews)
"The warm cookie at check-in from Tyler was a thoughtful and welcoming gesture. I appreciated the friendly front desk team, the clean and comfortable room, and the hotel’s convenient location. The overall ambiance was inviting and well cared for."

Reviewed on Jun 29, 2025

DoubleTree by Hilton Hotel Annapolis
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! (1,010 reviews)
"Parking situation was awful and needs to be rethought. The extra cost for parking was ridiculous and spaces not sufficient for hotel capacity."

Reviewed on Jun 27, 2025

Hilton Garden Inn Annapolis Downtown
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! (830 reviews)
"The room was very nice. But the staff who serviced the room was not very good. Many days we did not have a shower mat, or extra toilet paper, or extra towels."

Reviewed on Jun 21, 2025

Annapolis Waterfront Hotel, Autograph Collection
Sonesta ES Suites Annapolis
Sonesta ES Suites Annapolis
3 out of 5
170 Admiral Cochrane Dr, Edgewater, MD
  • 38 min drive from St. Michaels Winery
Book a stay at this business-friendly hotel in Edgewater. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (828 reviews)
"Need to do more thorough cleanings. Staff was helpful"

Reviewed on Jun 25, 2025

Sonesta ES Suites Annapolis
Best Western Annapolis
Best Western Annapolis
2.5 out of 5
2520 Riva Rd, Annapolis, MD
  • 39 min drive from St. Michaels Winery
Book a stay at this business-friendly hotel in Annapolis. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
7.8/10 Good! (1,007 reviews)
Comfortable Stay
"Beds were very comfortable. Location close to everything."

Reviewed on Jun 29, 2025

Best Western 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! (1,009 reviews)
"Property was clean. Staff was friendly. Beds and pillows were not very comfortable. Breakfast had a good variety but stayed the same. Good location."

Reviewed on Jun 30, 2025

Country Inn & Suites by Radisson, Annapolis, MD
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 ...
9.4/10 Exceptional! (1,010 reviews)
"We enjoyed our stay. Friendly. Comfortable. Parking is pricey."

Reviewed on Jun 28, 2025

Graduate by Hilton Annapolis
Hyatt Regency Chesapeake Bay
Hyatt Regency Chesapeake Bay
4 out of 5
100 Heron Blvd, Cambridge, MD
  • 40 min drive from St. Michaels Winery
Stay at this 4-star beach resort in Cambridge. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
8.6/10 Excellent! (1,001 reviews)
"The Hyatt is a great stay. Balconies outside need painting. Staff and amenities otherwise are great."

Reviewed on Jun 22, 2025

Hyatt Regency Chesapeake Bay
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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