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Hotels in St. Michaels

Choose from 1235 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 $604 per night from May 4 to May 5
$604
includes taxes & fees
May 4 - May 5
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! (344 reviews)
"A true 5-star experience from the moment we pulled up. Highly recommend a sail with Captain Sean, participating in the 5pm toast, and staying for longer than the one night that we did! We’ll be back!"

Reviewed on Apr 27, 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 $136 per night from May 1 to May 2
$136
includes taxes & fees
May 1 - May 2
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! (1,005 reviews)
Nice Stay
"Very cute property and perfect location for visiting St Michael’s. Staff was very friendly. Room was comfortable and clean. Grounds could use some TLC. Power washing furniture, trim bushes etc."

Reviewed on Apr 27, 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 $263 per night from May 4 to May 5
$263
includes taxes & fees
May 4 - May 5
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! (310 reviews)
"Great"

Reviewed on Apr 25, 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
The price is $253 per night from May 1 to May 2
$253
includes taxes & fees
May 1 - May 2
Stay at this 3-star B&B in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Perry Cabin Park and Chesapeake Bay Maritime ...
8.6/10 Excellent! (57 reviews)
"Very nice property, cozy and clean rooms, excellent service."

Reviewed on Sep 15, 2024

George Brooks House B&B
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 $199 per night from May 6 to May 7
$199
includes taxes & fees
May 6 - May 7
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! (1,755 reviews)
"Perfect"

Reviewed on Apr 27, 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 $115 per night from May 6 to May 7
$115
includes taxes & fees
May 6 - May 7
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! (1,002 reviews)
"I love the trees. I didn’t like the air wick plug in in my room though."

Reviewed on Apr 26, 2025

Country Inn & Suites by Radisson, Annapolis, MD
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 May 4 to May 5
$170
includes taxes & fees
May 4 - May 5
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! (1,002 reviews)
"Hotel was under renovation so things were covered in plastic, etc. but overall very nice."

Reviewed on Apr 23, 2025

The Westin 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
The price is $135 per night from May 27 to May 28
$135
includes taxes & fees
May 27 - May 28
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! (1,001 reviews)
"Clean and comfortable. Good location to downtown harbor area of Annapolis."

Reviewed on Apr 29, 2025

Hilton Garden Inn Annapolis Downtown
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 $275 per night from May 6 to May 7
$275
includes taxes & fees
May 6 - May 7
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! (1,000 reviews)
"Beautiful property and love movie night."

Reviewed on Apr 20, 2025

Hyatt Regency Chesapeake Bay
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 $159 per night from May 7 to May 8
$159
includes taxes & fees
May 7 - May 8
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! (526 reviews)
"The staff is always amazing!!!!"

Reviewed on Apr 25, 2025

Hyatt Place Kent Narrows & Marina
SpringHill Suites by Marriott Annapolis
SpringHill Suites by Marriott Annapolis
3 out of 5
189 Admiral Cochrane Drive, Annapolis, MD
  • 38 min drive from St. Michaels Winery
The price is $136 per night from May 1 to May 2
$136
includes taxes & fees
May 1 - May 2
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and ...
9/10 Wonderful! (1,003 reviews)
Annapolis stay
"The room was clean and the bed was very comfortable. The breakfast was also good. We enjoyed the stay. Thank you! I am hoping you won't charge for parking in the future."

Reviewed on Apr 25, 2025

SpringHill Suites by Marriott 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
The price is $193 per night from May 26 to May 27
$193
includes taxes & fees
May 26 - May 27
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! (1,005 reviews)
"We stayed in one of the 2 BDRM apartments and it was perfect for the 4 of us. We were a 15 minute walk to our family reunion and the neighborhood seemed safe, lots of people out walking their dogs, etc. The apartment was clean and very nicely furnished. We had a nice living room area where we could ..."

Reviewed on Apr 27, 2025

Graduate by Hilton 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.

Find cheap hotels in St. Michaels

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