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Hotels in St. Michaels

Choose from 1271 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 $692 per night from May 21 to May 22
$692
includes taxes & fees
May 21 - May 22
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 $129 per night from May 8 to May 9
$129
includes taxes & fees
May 8 - May 9
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! (1,004 reviews)
"Staff"

Reviewed on May 2, 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 8 to May 9
$263
includes taxes & fees
May 8 - May 9
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! (311 reviews)
Fabulous
"Fabulous birthday trip! Location staff and facility were over the top! Highly Reccommend."

Reviewed on May 1, 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 8 to May 9
$253
includes taxes & fees
May 8 - May 9
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 25 to May 26
$199
includes taxes & fees
May 25 - May 26
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! (1,763 reviews)
Great location, very comfortable
"Reception was great. Amazing location. Super comfortable. Got a free bottle of wine!"

Reviewed on May 3, 2025

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
The price is $183 per night from May 28 to May 29
$183
includes taxes & fees
May 28 - May 29
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! (1,004 reviews)
"Love the rooms and the quaintness of the town!"

Reviewed on May 1, 2025

Graduate by Hilton 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 $120 per night from May 27 to May 28
$120
includes taxes & fees
May 27 - May 28
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! (1,004 reviews)
"Clean and quiet"

Reviewed on May 3, 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 25 to May 26
$170
includes taxes & fees
May 25 - May 26
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! (1,003 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 $125 per night from May 27 to May 28
$125
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! (1,006 reviews)
"Great staff. Great town. Love First Sundays in NapTown."

Reviewed on May 5, 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 $159 per night from May 13 to May 14
$159
includes taxes & fees
May 13 - May 14
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! (530 reviews)
"Exactly what we were looking for."

Reviewed on May 4, 2025

Hyatt Place Kent Narrows & Marina
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 $319 per night from May 26 to May 27
$319
includes taxes & fees
May 26 - May 27
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! (1,001 reviews)
"Beautiful property and love movie night."

Reviewed on Apr 20, 2025

Hyatt Regency Chesapeake Bay
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
The price is $125 per night from May 27 to May 28
$125
includes taxes & fees
May 27 - May 28
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 ...
8.4/10 Very Good! (1,004 reviews)
"Super clean. Nice stay"

Reviewed on May 3, 2025

DoubleTree by Hilton Hotel 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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