Downtown St. Michaels Holidays
Book a Hotel + Flight or Car together to unlock savings
Top hotels in Downtown St. Michaels
The Wildset
209 N Talbot St St. Michaels MD
Fully refundableReserve now, pay when you stay
The price is 5.189.323 ₫ per night from 5 Feb to 6 Feb
5.189.323 ₫
6.281.949 ₫ total
5 Feb - 6 Feb
includes taxes & fees
9.6/10 Exceptional! (416 reviews)
Clean rooms, great staff, awesome restaurant on site called Ruse & right in downtown.
Reviewed on 21 Jan 2026
Inn at Perry Cabin
308 Watkins Ln St. Michaels MD
The price is 12.468.780 ₫ per night from 27 Feb to 28 Feb
12.468.780 ₫
13.715.658 ₫ total
27 Feb - 28 Feb
includes taxes & fees
9.4/10 Exceptional! (374 reviews)
We had a great stay, hotel was very clean and food was great
Reviewed on 3 Jan 2026
Parsonage Inn
210 North Talbot Street St. Michaels MD
The price is 3.885.473 ₫ per night from 2 Feb to 3 Feb
3.885.473 ₫
4.274.020 ₫ total
2 Feb - 3 Feb
includes taxes & fees
9.2/10 Wonderful! (130 reviews)
What a great stay! Beautiful B&B in St Michael’s! Our hosts Connie and Edward were very welcoming. Had great suggestions for dining and tourist attractions within the town. Our room was clean, comfortable and was perfect for our stay. The Inn also offers bikes to explore the area as well. Each afternoon, ...
Reviewed on 11 Aug 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.
Popular places to visit
Chesapeake Bay Maritime Museum
You can study the exhibits at Chesapeake Bay Maritime Museum, a museum with a storied past, during your travels to St. Michaels. Stroll along the waterfront or experience the area's museums.
St. Michaels Winery
You can enjoy a tasting or tour at St. Michaels Winery during your travels to St. Michaels. Discover the seafood restaurants and its museums while you're in the area.
Windon Distilling
You can take time to visit Windon Distilling during your travels to St. Michaels.