Downtown St. Michaels Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Downtown St. Michaels
Inn at Perry Cabin
308 Watkins Ln St. Michaels MD
S$721
26 Oct - 27 Oct
includes taxes & fees
9.6/10 Exceptional! (405 reviews)
"Outstanding experience in every way. Staff was superior — everyone greeted us by name and was eager to ensure we had everything we needed. Meals at Stars were excellent — and the gorgeous views of the water and property enhanced the dining experience. The lit firepits and comfy seating outside were ..."
Reviewed on 29 Sept, 2026
The Wildset
209 N Talbot St St. Michaels MD
S$368
27 Oct - 28 Oct
includes taxes & fees
Parsonage Inn
210 North Talbot Street St. Michaels MD
9.2/10 Wonderful! (138 reviews)
"Lots of issues with our room and stay. Small motel room with junk in the closet, marks on wall and door, and light bulb missing. TV and DVD not working. Outside unkempt. Breakfast not ver good. Substandard for price and advertisement."
Reviewed on 21 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.
Windon Distilling
You can take time to visit Windon Distilling during your travels to St. Michaels.
Things to do
St Michaels: 2-Hour Chesapeake Bay Sail on Lady Patty
S$203
per adult
St. Michaels: 2-Hour Relaxing Chesapeake Sail on Epiphany
S$345
per adult
St. Michaels: 2-Hour Wine Tasting on Sailing Cruise Epiphany
S$380
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.