St. Michaels Vacations from $885

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Your St. Michaels Vacation

The fascinating city of St. Michaels is calling your name. Immerse yourself in everything it has to offer with a St. Michaels vacation package that's tailored to you. You'll want to take in some sights during your trip to St. Michaels. Drop by major attractions such as St. Michaels Winery, Chesapeake Bay Maritime Museum and St. Michaels Museum. Stop daydreaming and start doing. Browse the many options on Expedia today and finally put your St. Michaels vacation plans in motion!

The Latest St. Michaels vacation packages

Price found within the past 48 hours. Click for updated prices.
Grand Hotel Ocean City Oceanfront
Americana Princess Suites and Condos
Club Ocean Villas II
Ocean Terrace Family Apartments
Boardwalk One
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St. Michaels Hotel Deals

St Michaels Inn
St Michaels Inn
2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
Fully refundable
$117 nightly
The price is $129 total per night from Jul 31 to Aug 1
$129 total
Jul 31 - Aug 1
Total includes taxes and fees
8/10 Very Good! (1,000 reviews)
Nice but aging
"This place is nice large and convenient, but is aging a little now. The breakfast is a nice to have but quite limited and bland compared with other places."

Reviewed on Jun 30, 2025

St Michaels Inn
Inn at Perry Cabin
Inn at Perry Cabin
5 out of 5
308 Watkins Ln, St. Michaels, MD
$678 nightly
The price is $746 total per night from Jul 16 to Jul 17
$746 total
Jul 16 - Jul 17
Total includes taxes and fees
9.4/10 Exceptional! (350 reviews)
Cool place but very pricey
"Fabulous place on the water. Nice pool, beautiful gardens, beautiful common areas. It seems a fair bit over priced though. We stayed for two weeknights and with the taxes, fees (and of course a $65 “resort fee” (haven’t they been banned yet) each night was pushing $800. The room was average size, ..."

Reviewed on Jun 27, 2025

Inn at Perry Cabin
The Wildset
The Wildset
2.5 out of 5
209 N Talbot St, St. Michaels, MD
Fully refundableReserve now, pay when you stay
$239 nightly
The price is $263 total per night from Jul 10 to Jul 11
$263 total
Jul 10 - Jul 11
Total includes taxes and fees
9.6/10 Exceptional! (329 reviews)
"Very nice place. The in house resturant was very good. Good location to sites. easy walk to most things."

Reviewed on Jun 27, 2025

The Wildset
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.

Find the Best St. Michaels Vacation Packages

St. Michaels Essential Information

Language
English
Currency
U.S dollars
Population
1,050
Max Temp Winter
45ºF
Max Temp Summer
80ºF
Top Sights
St. Michaels Winery, Avalon Theatre and Historical Society of Talbot County

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Frequently asked questions

How much does a St. Michaels vacation package cost?
You can snap up a vacation package to this destination from $885 on Expedia. However, how much your vacation to St. Michaels costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to St. Michaels?
You can typically find lower prices and greater availability in January, September and December. Browse our cheap St. Michaels vacation packages and you could land some excellent off-season deals.
How many days is enough for St. Michaels?
The ideal duration of your St. Michaels vacation depends on what you'd like to do. Generally, a handful of days to a week will give you enough time to go to all the main sights and discover some hidden spots along the way.
Is it worth booking a vacation package to St. Michaels?
St. Michaels has all the ingredients you need for a fantastic trip --- nature, culture and watersports are just the start. Whether you want to visit attractions like Chesapeake Bay Maritime Museum and St. Michaels Museum, or take the path less traveled, you'll have plenty to do on your St. Michaels vacation.
How to find the best St. Michaels package deals?
Use Expedia's filters to find some fabulous St. Michaels package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or search for St. Michaels package deals in the off-season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a St. Michaels vacation as a package?
You can enjoy significant savings on your next St. Michaels escape by booking a tailored vacation package. Check the "Package" heading, then enter your destination and travel dates to see some great airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to St. Michaels?
Land fantastic discounts by booking your flights in advance with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu St. Michaels break.
Does Expedia offer Book Now, Pay Later St. Michaels vacation packages?
Set off on your ideal getaway to St. Michaels with help from Expedia's Book Now, Pay Later vacations. There's no need to save up or wait until your next paycheck --- we've teamed up with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans let you spread the total cost over 3, 6 or 12 months. With no hidden charges or late payment fees, you can easily budget for your trip and snap up cheap deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.