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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! (1,002 reviews)
Basic room, clean and comfortable. Only complaint, it took 15 minutes to get hot water in the shower -- wasted a lot of water waiting. Good TV selection, too.
Reviewed on Oct 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! (368 reviews)
Friendly and attentive staff, good cleaning services
Reviewed on Oct 26, 2025

George Brooks House B&B
24500 Rolles Range Road, St. Michaels, MD
Stay at this 3-star B&B in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Perry Cabin Park and St Michaels Nature Trail ...
8.6/10 Excellent! (64 reviews)
Great, great property.
This is a true gem. The house and room were very warm, comfortable, and inviting. The staff were friendly, very helpful, and knowledgeable. Room was true to picture and description. Bed was very comfortable. Breakfast was delicious. Parking was easy and convenient. Would absolutely stay again.
Reviewed on Aug 1, 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 Chesapeake Bay
- Hotels near U.S. Naval Academy
- Hotels near Chesapeake Bay Bridge
- Hotels near Sandy Point State Park
- Hotels near Annapolis City Dock
- Hotels near Navy-Marine Corps Memorial Stadium
Cities near St. Michaels
- Annapolis Hotels (19.58 mi)
- Cambridge Hotels (17.02 mi)
- Easton Hotels (8.01 mi)
- Chestertown Hotels (30.99 mi)
- Stevensville Hotels (14.25 mi)
- Grasonville Hotels (11.87 mi)
- Chesapeake Beach Hotels (17.85 mi)
- North Beach Hotels (17.4 mi)
- Eastern Shore Hotels (21.5 mi)
- Pasadena Hotels (29.78 mi)
- Rock Hall Hotels (24.28 mi)
- Tilghman Hotels (8.4 mi)
- Edgewater Hotels (21.08 mi)
- Prince Frederick Hotels (25.8 mi)
- Arnold Hotels (22.6 mi)
- Oxford Hotels (7.47 mi)
- Centreville Hotels (19.56 mi)
- Queenstown Hotels (14.54 mi)
- Deale Hotels (17.82 mi)
- Denton Hotels (22.21 mi)
