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!

Ready to book your vacation to St. Michaels?

 

Choose your dates

St. Michaels Hotel Deals

Inn at Perry Cabin
Inn at Perry Cabin
5 out of 5
308 Watkins Ln, St. Michaels, MD
The price is CA $691 per night from May 4 to May 5
CA $691
CA $836 total
includes taxes & fees
May 4 - May 5
9.4/10 Exceptional! (344 reviews)
"A true 5-star experience from the moment we pulled up. Highly recommend a sail with Captain Sean, participating in the 5pm toast, and staying for longer than the one night that we did! We’ll be back!"

Reviewed on Apr. 27, 2025

Inn at Perry Cabin
St Michaels Inn
St Michaels Inn
2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
The price is CA $171 per night from May 1 to May 2
CA $171
CA $188 total
includes taxes & fees
May 1 - May 2
8/10 Very Good! (1,005 reviews)
Nice Stay
"Very cute property and perfect location for visiting St Michael’s. Staff was very friendly. Room was comfortable and clean. Grounds could use some TLC. Power washing furniture, trim bushes etc."

Reviewed on Apr. 27, 2025

St Michaels Inn
The Wildset
The Wildset
2.5 out of 5
209 N Talbot St, St. Michaels, MD
Fully refundableReserve now, pay when you stay
The price is CA $303 per night from May 4 to May 5
CA $303
CA $364 total
includes taxes & fees
May 4 - May 5
9.6/10 Exceptional! (310 reviews)
"Great"

Reviewed on Apr. 25, 2025

The Wildset
See all 1,267 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.

All Inclusive Vacations

All Inclusive Vacations

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Frequently asked questions

How much does a St. Michaels vacation package cost?
You’ll find cheap prices 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.