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$805
26 Oct - 27 Oct
includes taxes & fees
Inn at Perry Cabin
The Wildset

The Wildset

209 N Talbot St St. Michaels MD
Fully refundableReserve now, pay when you stay
AU$411
5 Oct - 6 Oct
includes taxes & fees
The Wildset
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

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

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John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
See all 756 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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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 travels 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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Muskrat Park

After visiting Muskrat Park, make a plan to see the other sights and activities in St. Michaels.
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Activities

St Michaels: 2-Hour Chesapeake Bay Sail on Lady Patty

St Michaels: 2-Hour Chesapeake Bay Sail on Lady Patty

AU$222
per adult
St Michaels: 2-Hour Chesapeake Bay Sail on Lady Patty
Epiphany

2 Hour Chesapeake Day Sail on Catamaran Epiphany

AU$342
per adult
2 Hour Chesapeake Day Sail on Catamaran Epiphany
St. Michaels: 2-Hour Relaxing Chesapeake Sail on Epiphany

St. Michaels: 2-Hour Relaxing Chesapeake Sail on Epiphany

AU$377
per adult
St. Michaels: 2-Hour Relaxing Chesapeake Sail on Epiphany
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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.