
Downtown St. Michaels Vacations from $741
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The Latest Downtown St. Michaels Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Boardwalk One
Downtown Ocean City
Price was $891, price is now $741 per person
$741
per person
Feb 1 - Feb 8
found 15 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Salisbury (SBY)
7.4/10 Good! (170 reviews)
Got better than what I expected for the price. Front desk ladies were happy & helpfully. Only thing that would be nice would be some type of dimmer lights for night, outlets near beds & softer beds. Will definately be staying here again! Full kitchen with full size fridge saved us $ not having to eat out. It's like a hotel sized condo.
Reviewed on Oct 1, 2025

The Shore House
West Ocean City
Save 100% on your flight
Price was $4,346, price is now $3,299 per person
$3,299
per person
Feb 1 - Feb 8
found 15 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Salisbury (SBY)
6.8/10 (598 reviews)
Overall it was perfect for country calling. There’s a shuttle at the hotel next door that we took everyday down to the entrance for $5 cash. The beds were comfortable, clean and the shower water was hot. I almost ended up cancelling though because during the off season it is nearly impossible to reach the hotel!! I called probably 10 times and couldn’t get an answer on my booking until Expedia themselves contacted me about changing the days we were staying. While the location was great, convenient and good for the price for country calling, the lack of communication was just shocking. As someone who travels often this customer service really needs to improve or I think sales will really suffer.
Reviewed on Oct 5, 2025

Miramar Condominiums
Downtown Ocean City
Price was $1,631, price is now $1,313 per person
$1,313
per person
Feb 1 - Feb 8
found 15 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Salisbury (SBY)
9.4/10 Exceptional! (15 reviews)
Stayed in unit 505 and it was beautiful! We loved it!
Reviewed on Aug 23, 2025

Beach Walk
Downtown Ocean City
Save 100% on your flight
Price was $4,313, price is now $3,577 per person
$3,577
per person
Feb 1 - Feb 8
found 15 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Salisbury (SBY)
7.6/10 Good! (95 reviews)
Everything was exactly what you would expect for a budget friendly room, only complaint was that the steps and porch going to 3rd floor was sketchy and theres a large soft spot on 3rd floor side landing
Reviewed on Oct 17, 2025

Grand Hotel Ocean City Oceanfront
Downtown Ocean City
Price was $915, price is now $762 per person
$762
per person
Feb 1 - Feb 8
found 15 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Salisbury (SBY)
9/10 Wonderful! (3,316 reviews)
Clean room , great view , efficient check in
Reviewed on Dec 11, 2025
Downtown St. Michaels Hotel Deals

Inn at Perry Cabin
308 Watkins Ln St. Michaels MD
$517 nightly
The price is $568 total per night from Dec 14 to Dec 15
$568 total
Dec 14 - Dec 15
Total with taxes and fees
9.4/10 Exceptional! (371 reviews)
Fantastic resort; beautiful with lots of great history. Highly recommend the historic walking tour with Jay.
Reviewed on Nov 12, 2025

The Wildset
209 N Talbot St St. Michaels MD
Fully refundableReserve now, pay when you stay
$219 nightly
The price is $241 total per night from Dec 14 to Dec 15
$241 total
Dec 14 - Dec 15
Total with taxes and fees
9.6/10 Exceptional! (408 reviews)
Nice large room. Free breakfast was good.
Reviewed on Dec 7, 2025

Parsonage Inn
210 North Talbot Street St. Michaels MD
$200 nightly
The price is $220 total per night from Jan 1 to Jan 2
$220 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
9.2/10 Wonderful! (130 reviews)
What a great stay! Beautiful B&B in St Michael’s! Our hosts Connie and Edward were very welcoming. Had great suggestions for dining and tourist attractions within the town. Our room was clean, comfortable and was perfect for our stay. The Inn also offers bikes to explore the area as well. Each afternoon, ...
Reviewed on Aug 11, 2025
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.
Discover the most popular places to visit in Downtown St. Michaels

Chesapeake Bay Maritime Museum
4.5/5(15 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 Winery
4.5/5(45 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.
St. Michaels Museum
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.


















