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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! (1,001 reviews)
Good value and close to downtown.

Reviewed on Dec 31, 2025

St Michaels Inn
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! (412 reviews)
Super clean room! Excellent breakfast. Very comfortable bed and linens. Great happy hour downstairs. Love making s'mores by the fire pit. Very lovely staff. Great to see Veronica again!

Reviewed on Dec 30, 2025

The Wildset
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! (373 reviews)
We had a great stay, hotel was very clean and food was great

Reviewed on Jan 3, 2026

Inn at Perry Cabin
George Brooks House B&B

George Brooks House B&B

3 out of 5
24500 Rolles Range Road St. Michaels MD
  • 22 min walk from St. Michaels Winery
Stay at this B&B in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Perry Cabin Park and St Michaels Nature Trail are located ...
8.6/10 Excellent! (65 reviews)
We were in St. Michaels for a wedding. We are planning on returning for a longer stay in the future.

Reviewed on Nov 2, 2025

George Brooks House B&B
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 B&B in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Perry Cabin Park and Higgins Yacht Yard and Marina are ...
9.2/10 Wonderful! (130 reviews)
What a great stay! Beautiful B&B in St Michael’s! Our hosts Connie and Edward were very welcoming. Had great suggestions for dining and tourist attractions within the town. Our room was clean, comfortable and was perfect for our stay. The Inn also offers bikes to explore the area as well. Each afternoon, ...

Reviewed on Aug 11, 2025

Parsonage Inn
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
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the ...
8.6/10 Excellent! (1,003 reviews)
The room was excellent, and the staff was as well. Special kudos to Jody behind the desk. The hotel bar /restaurant is fantastic and the bartender, Carlos, was amazing! We had a great time in the bar ringing in the new year.

Reviewed on Jan 1, 2026

DoubleTree by Hilton Hotel 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
Book a stay at this 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! (1,003 reviews)
Pleasant staff. Good location to walk to restaurants, shops.

Reviewed on Dec 30, 2025

Graduate by Hilton Annapolis
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! (1,907 reviews)
Staff was exceptionally friendly & helpful. Room clean & tastefully appointed. Location was perfectly situated in the old town & near antique stores, Main Street & the harbor. Great getaway!

Reviewed on Jan 1, 2026

Historic Inns of Annapolis
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
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.6/10 Excellent! (1,018 reviews)
Easy

Reviewed on Jan 4, 2026

Crowne Plaza Annapolis by IHG
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
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff ...
8.8/10 Excellent! (895 reviews)
Was disappointed that I expected a balcony but got the parking lot view and no balcony. Rooms were changed from my reservation for a King bed to two full size beds without my knowledge. Beds were comfortable. Shower water pressure was not the best. Very beautiful downtown with lots of shopping and ...

Reviewed on Jan 2, 2026

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
Book a stay at this 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! (1,005 reviews)
Great rooms, amenities, staff

Reviewed on Dec 29, 2025

Hyatt Regency Chesapeake Bay
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
Book a stay at this 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! (1,007 reviews)
Everything was clean and in working order in the room. Staff was friendly and efficient. Location was perfect. Would definitely stay here again.

Reviewed on Jan 2, 2026

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.

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