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Hotels in St. Michaels

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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! (1,000 reviews)
"The room was clean and the staff was very helpful. Minutes to downtown St Michaels."

Reviewed on Jul 29, 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! (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! (344 reviews)
Generous people and place
"Perfect from arrival to departure. We did happy hour at the restaurant which was high value and delicious. They also have a luxurious garden fire pit and smores experience included during summer. Continental breakfast also included. It’s such a well-run, generous experience that reminds me of Sonoma ..."

Reviewed on Jul 27, 2025

The Wildset
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! (1,832 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 ...
9.4/10 Exceptional! (1,008 reviews)
"Beautiful place, very clean room, but the best thing by far was the staff. Everyone we met was friendly and helpful. Thank you so much for a greay stay!!"

Reviewed on Jul 27, 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! (1,000 reviews)
7 out of 10 stars
"The hotel is older and as we walked through we were saying how it could be (& you can tell it was) a really nice hotel. Don’t misunderstand, it was a nice hotel, but you can tell it’s ‘used’. There are scuffs on doors and walls, there are tiles broken on floors, etc. the room itself was clean. The ..."

Reviewed on Jul 27, 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! (1,015 reviews)
"The bed was wonderful! The room temperature was excellent! The accessible shower was amazing. The lovely lady who checked us in upon arrival was so helpful and friendly she deserves a raise!"

Reviewed on Jul 27, 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! (847 reviews)
Nice for a brief stay
"Great location and close to great restaurants. While pet friendly it was difficult to find a doggy potty area. The bathroom had had a leak that was barely patched and the bath had no fan. The parking was valet and we thought our car was parked in an enclosed area but we later saw it in a school parking ..."

Reviewed on Jul 24, 2025

Annapolis Waterfront Hotel, Autograph Collection
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! (1,006 reviews)
"My issue was with the bedding, it was not very comfortable"

Reviewed on Jul 24, 2025

Hyatt Regency Chesapeake Bay
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! (1,005 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
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! (1,008 reviews)
"Great location"

Reviewed on Jul 28, 2025

Hilton Garden Inn Annapolis Downtown
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.

Find cheap hotels in St. Michaels

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