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Hotels in St. Michaels

Choose from 1237 St. Michaels Hotel Deals

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
The price is $517 per night from Mar 26 to Mar 27
$517
includes taxes & fees
Mar 26 - Mar 27
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! (335 reviews)
"Very enjoyable stay."

Reviewed on Mar 14, 2025

Inn at Perry Cabin
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
The price is $110 per night from Mar 26 to Mar 27
$110
includes taxes & fees
Mar 26 - Mar 27
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)
First visit
"This was the first time here and this is a good location and a good value."

Reviewed on Mar 22, 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
The price is $230 per night from Mar 26 to Mar 27
$230
includes taxes & fees
Mar 26 - Mar 27
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! (303 reviews)
"This is a very tasteful hotel, based in three buildings, and with a feeling of simple luxury. All the staff are very nice and helpful. My room was lovely, and the bed was excellent. Two tiny notes: the boat lock on the room door did not function, and one of the window blinds had a broken slat. These ..."

Reviewed on Mar 10, 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
The price is $198 per night from Mar 26 to Mar 27
$198
includes taxes & fees
Mar 26 - Mar 27
Stay at this 3.5-star B&B in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Higgins Yacht Yard and Marina and Chesapeake ...
9/10 Wonderful! (127 reviews)
"exceptional hosts: above and beyond for service, suggestions, accommodation, effort to assist . impressive found by accident, would reccommend and visit AGAIN"

Reviewed on Mar 17, 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
The price is $180 per night from Mar 31 to Apr 1
$180
includes taxes & fees
Mar 31 - Apr 1
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! (1,727 reviews)
"Love the convenience that we valet parked the car and didn’t need it again until we checked out. Felt totally safe as we walked around to first class shops and restaurants. The property was clean and comfortable. We had an issue with the pillows on the bed. Too new and full. Called to the desk and ..."

Reviewed on Mar 23, 2025

Historic Inns of 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
The price is $101 per night from Apr 1 to Apr 2
$101
includes taxes & fees
Apr 1 - Apr 2
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 ...
8.8/10 Excellent! (1,001 reviews)
"well kept"

Reviewed on Mar 25, 2025

Country Inn & Suites by Radisson, Annapolis, MD
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
The price is $125 per night from Mar 31 to Apr 1
$125
includes taxes & fees
Mar 31 - Apr 1
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! (1,000 reviews)
"Recommend"

Reviewed on Mar 25, 2025

Crowne Plaza Annapolis by IHG
The Westin Annapolis
The Westin Annapolis
4 out of 5
100 Westgate Cir, Annapolis, MD
  • 37 min drive from St. Michaels Winery
The price is $170 per night from Apr 6 to Apr 7
$170
includes taxes & fees
Apr 6 - Apr 7
Stay at this 4-star spa hotel in Annapolis. Enjoy a full-service spa, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. ...
8.6/10 Excellent! (999 reviews)
"I loved it"

Reviewed on Mar 20, 2025

The Westin 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
The price is $283 per night from Apr 21 to Apr 22
$283
includes taxes & fees
Apr 21 - Apr 22
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! (1,002 reviews)
"we arrived early and we were checked right in"

Reviewed on Mar 17, 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
The price is $96 per night from Apr 13 to Apr 14
$96
includes taxes & fees
Apr 13 - Apr 14
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 ...
8.6/10 Excellent! (1,004 reviews)
"Beautiful room. Staff was great."

Reviewed on Mar 23, 2025

Hilton Garden Inn Annapolis Downtown
Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & Marina
3 out of 5
3028 KENT NARROW WAY S, Grasonville, MD
  • 31 min drive from St. Michaels Winery
The price is $121 per night from Apr 23 to Apr 24
$121
includes taxes & fees
Apr 23 - Apr 24
Stay at this 3-star business-friendly hotel in Grasonville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
9.4/10 Exceptional! (502 reviews)
"Loved the location on the waterfront and the views from the room. Our room had a small kitchen which was convenient."

Reviewed on Mar 22, 2025

Hyatt Place Kent Narrows & Marina
Courtyard by Marriott Annapolis
Courtyard by Marriott Annapolis
3 out of 5
2559 Riva Rd, Annapolis, MD
  • 38 min drive from St. Michaels Winery
The price is $106 per night from Mar 30 to Mar 31
$106
includes taxes & fees
Mar 30 - Mar 31
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.4/10 Very Good! (986 reviews)
"Friendly staff"

Reviewed on Mar 24, 2025

Courtyard by Marriott Annapolis
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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