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Featured St. Michaels Family Hotels

St Michaels Inn
1228 S Talbot Street St. Michaels MD
Fully refundable
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 ...

Inn at Perry Cabin
308 Watkins Ln St. Michaels MD
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. ...
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.
Hotels with Pools in St. Michaels

St Michaels Inn
1228 S Talbot Street St. Michaels MD
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)
This is a charming little inn conveniently located right in St Michaels. The staff was great, the rooms clean, and plenty of parking. In the warmer months you can enjoy the pool and roomy outdoor seating areas.
Reviewed on Nov 17, 2025

Inn at Perry Cabin
308 Watkins Ln St. Michaels MD
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

George Brooks House B&B
24500 Rolles Range Road St. Michaels MD
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
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.
Hotels With Connecting Rooms in St. Michaels

Inn at Perry Cabin
308 Watkins Ln St. Michaels MD
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. ...
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.
Hotels by Star Rating
More Hotel Options
- Hotels with a Pool in St. Michaels
- Historic Hotels in St. Michaels
- Hotels with Free Parking in St. Michaels
- Romantic Hotels in St. Michaels
- Pet-friendly Hotels in St. Michaels
- Oceanfront Hotels in St. Michaels
- Hotel Wedding Venues in St. Michaels
- Hotels with Hot Tubs in St. Michaels
- Resorts & Hotels with Spas in St. Michaels
- Beach Hotels in St. Michaels
Top Points of Interests in St. Michaels
- Hotels near St. Michaels Winery
- Hotels near Chesapeake Bay Maritime Museum
- Hotels near St. Michaels Museum
- Hotels near Windon Distilling
- Hotels near St Michaels Nature Trail
- Hotels near U.S. Naval Academy
- Hotels near Navy-Marine Corps Memorial Stadium
- Hotels near Annapolis City Dock
- Hotels near Chesapeake Bay Bridge
- Hotels near Anne Arundel Medical Center
- Hotels near Chesapeake Bay
Cities near St. Michaels
- Annapolis Hotels (19.58 mi)
- Easton Hotels (8.01 mi)
- Cambridge Hotels (17.02 mi)
- Stevensville Hotels (14.25 mi)
- Chestertown Hotels (30.99 mi)
- Grasonville Hotels (11.87 mi)
- Chesapeake Beach Hotels (17.85 mi)
- Eastern Shore Hotels (21.5 mi)
- Pasadena Hotels (29.78 mi)
- Edgewater Hotels (21.08 mi)
- Prince Frederick Hotels (25.8 mi)
- Rock Hall Hotels (24.28 mi)
- North Beach Hotels (17.4 mi)
- Tilghman Hotels (8.4 mi)
- Arnold Hotels (22.6 mi)
- Oxford Hotels (7.47 mi)
- Queenstown Hotels (14.54 mi)
- Deale Hotels (17.82 mi)
- Centreville Hotels (19.56 mi)
- Denton Hotels (22.21 mi)
