Downtown St. Michaels Vacations

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Downtown St. Michaels Hotel Deals

Inn at Perry Cabin

Inn at Perry Cabin

308 Watkins Ln St. Michaels MD
NT$16,367
NT$18,004 total
Oct 26 - Oct 27
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 2026/9/29

Inn at Perry Cabin
The Wildset

The Wildset

209 N Talbot St St. Michaels MD
Fully refundableReserve now, pay when you stay
NT$7,614
NT$9,171 total
Oct 27 - Oct 28
includes taxes & fees
The Wildset
Parsonage Inn

Parsonage Inn

210 North Talbot Street St. Michaels MD
NT$9,238
NT$10,162 total
Nov 1 - Nov 2
includes taxes & fees
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 2026/8/21

Parsonage Inn
See all 751 properties in Downtown St. Michaels
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

A lighthouse on stilts with a green roof, surrounded by water and greenery.
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 trip to St. Michaels. Stroll along the waterfront or experience the area's museums.
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A marina with several sailboats docked in calm waters.

St. Michaels Marina

Explore the waterfront in St. Michaels with a trip to St. Michaels Marina.
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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.
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Saint Michaels Town Hall

After visiting Saint Michaels Town Hall, make a plan to see the other sights and activities in St. Michaels.
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1879 Hooper Straight Lighthouse

After visiting 1879 Hooper Straight Lighthouse, make a plan to see the other sights and activities in St. Michaels.
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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 trip to St. Michaels. Discover the seafood restaurants and its museums while you're in the area.
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St Michaels Nature Trail

You can take time to visit St Michaels Nature Trail during your travels to St. Michaels.
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Windon Distilling

You can take time to visit Windon Distilling during your travels to St. Michaels.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.