Downtown St. Michaels Holidays
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Top hotels in Downtown St. Michaels
Inn at Perry Cabin
308 Watkins Ln St. Michaels MD
£426
26 Oct - 27 Oct
includes taxes & fees
The Wildset
209 N Talbot St St. Michaels MD
Fully refundableReserve now, pay when you stay
£217
5 Oct - 6 Oct
includes taxes & fees
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Saint Michaels MD
9.6/10 Exceptional! (134 reviews)
"Location was perfect and we enjoyed the sunrise every morning. Walkable to everything in St. Michael’s. Beautiful historic home and furnishings. A great stay!!"
Reviewed on 24 Aug 2026
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.
Stay near popular Downtown St. Michaels attractions
Photo by Louise Johnson
Chesapeake Bay Maritime Museum
9.4/10 (91 reviews)
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 Marina
Explore the waterfront in St. Michaels with a trip to St. Michaels Marina.
St. Michaels Winery
8.6/10 (91 reviews)
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.
Saint Michaels Town Hall
After visiting Saint Michaels Town Hall, make a plan to see the other sights and activities in St. Michaels.
1879 Hooper Straight Lighthouse
After visiting 1879 Hooper Straight Lighthouse, make a plan to see the other sights and activities in St. Michaels.
St. Michaels Museum
8.6/10 (9 reviews)
You can browse the exhibits at St. Michaels Museum, a museum with a storied past, during your travels to St. Michaels. Discover the seafood restaurants and its museums while you're in the area.
St Michaels Nature Trail
You can take time to visit St Michaels Nature Trail during your travels to St. Michaels.
Muskrat Park
After visiting Muskrat Park, make a plan to see the other sights and activities in St. Michaels.
Things to do
St Michaels: 2-Hour Chesapeake Bay Sail on Lady Patty
£119
per adult
St. Michaels: 2-Hour Relaxing Chesapeake Sail on Epiphany
£202
per adult
2 Hour Chesapeake Day Sail on Catamaran Epiphany
£183
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.