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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 location

Reviewed on Jan 19, 2026

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! (416 reviews)
Clean rooms, great staff, awesome restaurant on site called Ruse & right in downtown.

Reviewed on Jan 21, 2026

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

Reviewed on Jan 3, 2026

Inn at Perry Cabin
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! (1,005 reviews)
Staff were extremely helpful and responsive when the first room was moldy/mildewy and helped get us into a new room quickly

Reviewed on Jan 19, 2026

DoubleTree by Hilton Hotel 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! (1,010 reviews)
Parking was close and convenient. Easy to access.

Reviewed on Jan 19, 2026

Crowne Plaza Annapolis by IHG
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 ...
9/10 Wonderful! (1,898 reviews)
YES

Reviewed on Jan 20, 2026

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
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! (1,008 reviews)
Hotel is obviously not new. However it is very well maintained, very clean and we had a pleasant stay. Staff were professional and polite and allowed us an early checkin. Onsite restaurant was pretty good as well. Would stay again.

Reviewed on Jan 21, 2026

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
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)
I LOVED IT AS DID MY KIDS!!!!!

Reviewed on Jan 21, 2026

Hyatt Regency Chesapeake Bay
The Westin Annapolis

The Westin Annapolis

4 out of 5
100 Westgate Cir Annapolis MD
  • 37 min drive from St. Michaels Winery
Book a stay at this spa hotel in Annapolis. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
8.6/10 Excellent! (1,002 reviews)
Clean room. Front desk was great and attentive. Ms. Shirley's restaurant is walking distance which is an amazing plus.

Reviewed on Jan 22, 2026

The Westin Annapolis
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! (899 reviews)
Very welcoming and room very clean.

Reviewed on Jan 4, 2026

Annapolis Waterfront Hotel, Autograph Collection
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
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 ...
9/10 Wonderful! (1,006 reviews)
The staff was so Friendly and helpful the Hotel was clean and decorated so nicely. Very good experience I can’t wait to get back to that Jacuzzi lol

Reviewed on Jan 18, 2026

Country Inn & Suites by Radisson, Annapolis, MD
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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