St. Michaels Vacations

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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!

Discover the most popular places to visit in St. Michaels

Chesapeake Bay Maritime Museum

Chesapeake Bay Maritime Museum

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.

Chesapeake Bay Maritime Museum

St. Michaels Winery

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 Winery

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.

St. Michaels Museum

St. Michaels Hotel Deals

St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
Fully refundable
$100 nightly
The price is $111 total per night from Nov 6 to Nov 7
$111 total
Nov 6 - Nov 7
Total with taxes and fees
8/10 Very Good! (1,002 reviews)
Basic room, clean and comfortable. Only complaint, it took 15 minutes to get hot water in the shower -- wasted a lot of water waiting. Good TV selection, too.

Reviewed on Oct 17, 2025

St Michaels Inn
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln, St. Michaels, MD
$382 nightly
The price is $420 total per night from Nov 18 to Nov 19
$420 total
Nov 18 - Nov 19
Total with taxes and fees
9.4/10 Exceptional! (368 reviews)
Friendly and attentive staff, good cleaning services

Reviewed on Oct 26, 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
$249 nightly
The price is $274 total per night from Nov 5 to Nov 6
$274 total
Nov 5 - Nov 6
Total with taxes and fees
9.6/10 Exceptional! (395 reviews)
We loved the FRESH (and free) breakfast. The room was great. Liked the big shower and having our own entrance. The vibe/atmosphere at the Ruse was great. Good customer service/friendly staff.

Reviewed on Oct 29, 2025

The Wildset
See all 1,275 properties in 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.

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 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.

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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.