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
$94 nightly
The price is $104 total per night from Oct 1 to Oct 2
$104 total
Oct 1 - Oct 2
Total with taxes and fees
8/10 Very Good! (1,004 reviews)
"When it takes two tries to get the room key to"

Reviewed on Sep 16, 2025

St Michaels Inn
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln, St. Michaels, MD
$535 nightly
The price is $588 total per night from Oct 1 to Oct 2
$588 total
Oct 1 - Oct 2
Total with taxes and fees
9.4/10 Exceptional! (363 reviews)
"Nice place to stay. Thru can’t do enough for you to make your stay comfortable and enjoyable Rooms are beautiful and clean"

Reviewed on Sep 11, 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 Oct 6 to Oct 7
$263 total
Oct 6 - Oct 7
Total with taxes and fees
9.6/10 Exceptional! (378 reviews)
Friendly Staff
"The hotel was clean. It had modern decor. As a plus there was a restaurant on site. The staff was friendly and stayed in touch by text message. The drawbacks for us were that there was no coffee maker in the room and parking spaces were limited."

Reviewed on Sep 18, 2025

The Wildset
See all 1,288 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.

Things to do in and around St. Michaels

St. Michaels, Maryland, is perfect for outdoor, romantic, and family vacations. Visitors can enjoy the scenic boardwalk and recreational areas, as well as exciting activities like boat tours, sailing adventures, and private tours. Don't miss out on the enchanting sunset cruises that showcase the beauty of this charming town. Explore St. Michaels for a delightful getaway filled with memorable experiences.

Shopping

In St. Michaels, explore the charming Saint Michaels Village, perfect for gifts with a family-friendly vibe. If you're up for a drive, visit the Queenstown Premium Outlets 14 miles away for a variety of brand-name bargains, or check out Easton Cycle and Sport, located 9 miles away.

Recreation

At Avalon Theatre, enjoy a captivating performance in a charming atmosphere that blends culture and romance. Hog Neck Golf Course offers a scenic outdoor experience for golf enthusiasts. For ultimate relaxation, Talbot Massage provides soothing body treatments designed to rejuvenate your mind and body.

Adventure

Experience the thrills at Chesapeake Beach Water Park, located 18 miles from St. Michaels, featuring exciting water slides and family-friendly attractions. For outdoor adventure, try the Annapolis Sailing School, also 18 miles away, where you can learn to sail and enjoy the beautiful waters.

For a fun indoor adventure, head to Annapolis Bowl, located 23 miles from St. Michaels, where you can enjoy bowling and arcade games in a lively atmosphere perfect for families.

Nightlife

St. Michaels offers a charming nightlife with venues like the lively Town Dock Restaurant, perfect for waterfront dining and drinks. For a laid-back vibe, visit the St. Michaels Winery, where you can enjoy tastings and local music in a cozy setting.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around St. Michaels

St. Michaels, Maryland, is perfect for outdoor enthusiasts and families, offering a charming blend of romantic getaways and cultural experiences. Explore the local marina, visit the historical museum, and enjoy the scenic urban park. The nearby Miles River adds to the area's allure, making it an ideal destination for travelers seeking adventure and relaxation in a picturesque setting.

  • Chesapeake Bay Maritime Museum: Immerse yourself in the rich maritime history of the Chesapeake Bay at this engaging museum. Explore historic vessels, interactive exhibits, and picturesque waterfront views that celebrate the region's culture and maritime heritage.
  • St. Michaels Museum: Delve into the local history at St. Michaels Museum, where you can discover artifacts and stories that highlight the town's past. The museum's charming setting offers a glimpse into the lives of those who shaped this unique community.
  • Pickering Creek Audubon Center: Experience nature at its finest at this eco-friendly center located 7 miles from St. Michaels. With trails, wildlife observation areas, and educational programs, it’s a haven for birdwatchers and outdoor enthusiasts alike.

Tips to save on your trip to St. Michaels

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling to St. Michaels during the low season (January to March) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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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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Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.