St. Michaels Vacation Packages
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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!
Top St. Michaels Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Comfort Inn & Suites Chestertown
CA $1,065
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Salisbury (SBY)
8.6/10 Excellent! (968 reviews)
Too many fly on the first floor, also the sheet is not clean, please make sure check sheet while you clean room
Reviewed on Sep 20, 2026
Ready to book your vacation to St. Michaels?
St. Michaels Hotel Deals
St Michaels Inn
1228 S Talbot Street St. Michaels MD
Fully refundableReserve now, pay when you stay
CA $120
CA $132 total
Sep 24 - Sep 25
includes taxes & fees
Inn at Perry Cabin
308 Watkins Ln St. Michaels MD
CA $846
CA $931 total
Oct 13 - Oct 14
includes taxes & fees
9.6/10 Exceptional! (403 reviews)
"Fantastic place; one of those that you don’t want to leave the property until the very sad time to go. Lovely staff, all of them, amazing food."
Reviewed on Sep 20, 2026
The Wildset
209 N Talbot St St. Michaels MD
Fully refundableReserve now, pay when you stay
CA $335
CA $404 total
Oct 5 - Oct 6
includes taxes & fees
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 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.
Saint Michaels Village
You can search for that perfect souvenir at Saint Michaels Village during your trip to St. Michaels. Stroll along this romantic area's waterfront, or simply enjoy its seafood restaurants.
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.
Saint Michaels Town Hall
After visiting Saint Michaels Town Hall, make a plan to see the other sights and activities in St. Michaels.
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 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.
Perry Cabin Park
After visiting Perry Cabin Park, make a plan to see the other sights and activities in St. Michaels. Stroll along the waterfront or visit the shops in this romantic area.
What to do in St. Michaels
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
St. Michaels: 2-Hour Relaxing Chesapeake Sail on Epiphany
CA $374
per adult
Frequently asked questions
How much does a St. Michaels vacation package cost?
You'll find cheap prices from CA $877 on Expedia for your St. Michaels break. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your vacation to St. Michaels costs.
What are the cheapest months to go to St. Michaels?
If you're looking to snag a cheap St. Michaels vacation package, consider planning a trip in January, February and March. You'll usually find lower rates on flights and hotels during these months — perfect for budget-conscious travellers.
How many days is enough for St. Michaels?
Usually, a handful of days is enough to go to the main attractions during your St. Michaels vacation. However, if you prefer to have more time to relax or go on day trips, consider extending your itinerary.
Is it worth booking a vacation package to St. Michaels?
Well known for its watersports, culture and nature, a St. Michaels vacation offers something for everyone. Be sure to visit major sights like Chesapeake Bay Maritime Museum and St. Michaels Museum, and consider renting some wheels for day trips to discover even more.
How to find the best St. Michaels package deals?
Bagging a cheap St. Michaels package deal is a cinch with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, apply a few filters and see what's available. You can personalize your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most affordable St. Michaels package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a St. Michaels vacation as a package?
You can enjoy significant savings on your next St. Michaels break by booking a tailored vacation package. Click on the "Package" heading, then select your travel dates and destination to browse some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to St. Michaels?
If you've got your St. Michaels vacation dates confirmed, book as soon as you can to grab some incredible deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for quick escapes.
How to plan a trip to St. Michaels?
- Pick the ideal time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to go to St. Michaels.
- Calculate your budget: Make sure you have enough money to cover everything from transportation and meals to experiences and flights. Your accommodations will likely be the biggest expense during your trip to St. Michaels.
- Decide how long to go for: Now that you're up to speed on St. Michaels, you can figure out the perfect length of your vacation. Pull together a draft itinerary and give yourself enough time to cover everything you want to see.
- Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a tailored St. Michaels vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
