St. Michaels Vacations

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Find the Best St. Michaels Vacation Packages

St. Michaels Hotel Deals

St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
The price is ₩139,380 per night from Sep 1 to Sep 2
₩139,380
₩153,321 total
Sep 1 - Sep 2
includes taxes & fees
8/10 Very Good! (1,003 reviews)
"We had a great time during our visit. Pool could use more seating and umbrellas. Rooms a bit dated. Overall, great time and would return. Great value for your money"

Reviewed on Jul 31, 2025

St Michaels Inn
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln, St. Michaels, MD
The price is ₩816,906 per night from Sep 1 to Sep 2
₩816,906
₩988,464 total
Sep 1 - Sep 2
includes taxes & fees
9.4/10 Exceptional! (356 reviews)
"Staff were wonderful, beautiful property and the restaurant was great. We enjoyed the complementary 5pm champagne toast and historical stories."

Reviewed on Aug 1, 2025

Inn at Perry Cabin
The Wildset

The Wildset

2.5 out of 5
209 N Talbot St, St. Michaels, MD
The price is ₩273,133 per night from Aug 19 to Aug 20
₩273,133
₩330,933 total
Aug 19 - Aug 20
includes taxes & fees
9.6/10 Exceptional! (348 reviews)
"Great location to all the shops and dining in the area. The room was spacious, very clean, and well decorated. Also loved the welcome gift for the dogs. Staff was also friendly and helpful. We had a wonderful stay."

Reviewed on Aug 2, 2025

The Wildset
See all 1,286 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.

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?
January, February and March are great times to search for cheap St. Michaels vacation packages. Traveling in quieter periods means you can typically find better prices on accommodations and flights.
How many days is enough for St. Michaels?
With a well-organized travel plan, you can easily visit the main St. Michaels sights in a handful of days. But if you want to venture off the beaten track or go on day tours, consider booking your St. Michaels vacation for longer.
Is it worth booking a vacation package to St. Michaels?
Well known for its watersports, culture and nature, a St. Michaels vacation is a hit with all kinds of travelers. Be sure to check out key sights like Chesapeake Bay Maritime Museum and St. Michaels Museum, and consider renting a set of wheels for day trips to experience even more.
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.
How to plan a trip to St. Michaels?

  1. Choose when to get away: Check your diary and get packing. Your favorite season and the available activities will also help you decide when to escape to St. Michaels.
  2. Plan your budget wisely: As well as the price of your hotel, you'll need to factor in other expenses. These include transportation, flights and food. Also, set aside some extra funds for unexpected expenses that may arise during your trip to St. Michaels.
  3. Set the duration of your trip: Start by compiling a list of the activities and sights you want to get to in St. Michaels. Then, estimate how long you'll need for each, including any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a personalized 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.