Downtown St. Michaels Holidays
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Top hotels in Downtown St. Michaels
Inn at Perry Cabin
308 Watkins Ln St. Michaels MD
Rp8.838.627
Rp9.722.490 total
7 Sept - 8 Sept
includes taxes & fees
9.6/10 Exceptional! (397 reviews)
"Amazing experience highly recommend"
Reviewed on 16 Aug 2026
The Wildset
209 N Talbot St St. Michaels MD
Fully refundableReserve now, pay when you stay
Rp4.260.653
Rp5.132.393 total
1 Sept - 2 Sept
includes taxes & fees
9.8/10 Exceptional! (499 reviews)
"Such a quaint hotel. The staff was incredibly kind and accommodating."
Reviewed on 16 Aug 2026
Parsonage Inn
210 North Talbot Street St. Michaels MD
9.2/10 Wonderful! (137 reviews)
"The Parsonage Inn is one of the most unique buildings on the main street through St. Michael's. We stayed in a room that faced the main street and it was amazingly quiet with respect to traffic noise. The decor is very old timey ... cute, quaint, and definitely fits the picture of what a B&B is. ..."
Reviewed on 27 Jun 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.
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 Nature Trail
You can take time to visit St Michaels Nature Trail during your travels to St. Michaels.
Saint Michaels Town Hall
After visiting Saint Michaels Town Hall, 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.
Higgins Yacht Yard and Marina
Explore the waterfront in St. Michaels with a trip to Higgins Yacht Yard and Marina.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.