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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! (1,003 reviews)
This was in a great location and a really cool atmosphere. We would definitely stay here again!

Reviewed on Nov 25, 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! (369 reviews)
Fantastic resort; beautiful with lots of great history. Highly recommend the historic walking tour with Jay.

Reviewed on Nov 12, 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! (406 reviews)
Clean modern room, Large bathroom

Reviewed on Nov 26, 2025

The Wildset
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
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! (1,009 reviews)
No hot shower in Suite for three days

Reviewed on Nov 19, 2025

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 ...
8.8/10 Excellent! (1,905 reviews)
Location perfect

Reviewed on Nov 23, 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
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! (1,027 reviews)
Clean, friendly staff. Restaurant/ bar food was excellent and staff in the restaurant/ bar were fun and accommodating!

Reviewed on Nov 26, 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
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! (1,010 reviews)
While it was a quick trip, we were very pleased with the late-check-in

Reviewed on Nov 24, 2025

Hilton Garden Inn Annapolis Downtown
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! (954 reviews)
clean and sanitized

Reviewed on Nov 20, 2025

Sonesta ES Suites 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
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 ...
8.8/10 Excellent! (1,009 reviews)
We liked the overall stay. We did have some issues but because the staff handled it with such grace and concern, we have no need to elaborate. Chrissy and Ashley were particularly empathetic and always willing to help or just extend an ear to listen. While no place is perfect, the service here was ...

Reviewed on Nov 25, 2025

Country Inn & Suites by Radisson, Annapolis, MD
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! (1,003 reviews)
Staff was fantastic, and although it was cooler due to the fall weather, there was still quite a few activities., Especially if you golf. Overall, slightly overpriced for the off-season in Cambridge, but clearly on point for warmer weather.

Reviewed on Nov 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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