Downtown St. Michaels Holidays

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Our pick of the best Downtown St. Michaels Hotel Deals

Inn at Perry Cabin

Inn at Perry Cabin

308 Watkins Ln St. Michaels MD
AU$968
26 Aug - 27 Aug
includes taxes & fees
Inn at Perry Cabin
The Wildset

The Wildset

209 N Talbot St St. Michaels MD
AU$407
1 Sept - 2 Sept
includes taxes & fees
9.8/10 Exceptional! (493 reviews)
"NA---breakfast and bar. The rooms were clean, well stocked and pleasantly decorated."

Reviewed on 6 Aug 2026

The Wildset
Parsonage Inn

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 June 2026

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Parsonage Inn
See all 749 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays
family friendly holidays
Family Friendly Holidays
Family Friendly Holidays
golf holidays
Golf Holidays
Golf Holidays
luxury holidays
Luxury Holidays
Luxury Holidays
romantic holidays
Romantic Holidays
Romantic Holidays
ski holidays
Ski Holidays
Ski Holidays
honeymoon holidays
Honeymoon Holidays
Honeymoon Holidays
pet friendly holidays
Pet-friendly Holidays
Pet-friendly Holidays
Spa Holidays
Spa Holidays
Spa Holidays

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 travels 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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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 Nature Trail

You can take time to visit St Michaels Nature Trail during your travels to St. Michaels.
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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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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.
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Higgins Yacht Yard and Marina

Explore the waterfront in St. Michaels with a trip to Higgins Yacht Yard and Marina.
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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.