Downtown St. Michaels Vacation Packages
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Top Holiday Package Deals in Downtown St. Michaels
Price found within the past 48 hours. Click for updated prices.
Castle in the Sand
Midtown Ocean City
CA $2,304
per person
Oct 15 - Oct 17
found 21 hours ago
Roundtrip flight included
Victoria (YYJ) to Salisbury (SBY)
8.8/10 Excellent! (1,019 reviews)
Second time staying at this hotel, always have a good time here the staff is always friendly and accommodating. I also love the restaurant on site. They’re happy hour buy one get one is a must and the fact that it’s right on the beach is another win.
Reviewed on Sep 11, 2026
Downtown St. Michaels Hotel Deals
Inn at Perry Cabin
308 Watkins Ln St. Michaels MD
CA $897
CA $986 total
Sep 13 - Sep 14
includes taxes & fees
9.6/10 Exceptional! (402 reviews)
"It’s so lovely and elegant I almost don’t want to tell people it’s there. Stunning, perfect in every way."
Reviewed on Sep 8, 2026
The Wildset
209 N Talbot St St. Michaels MD
Fully refundableReserve now, pay when you stay
CA $332
CA $399 total
Oct 5 - Oct 6
includes taxes & fees
9.8/10 Exceptional! (512 reviews)
"Room was clean and staff was super helpful and kind!"
Reviewed on Sep 11, 2026
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 Aug 24, 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 trip 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 trip 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.
Things to do
St Michaels: 2-Hour Chesapeake Bay Sail on Lady Patty
CA $220
per adult
2 Hour Chesapeake Day Sail on Catamaran Epiphany
CA $339
per adult
2-Hour Relaxing Chesapeake Day Sail on Lady Patty
CA $221
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.