St. Michaels Vacations

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Find the Best St. Michaels Vacation Packages

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 SAR 1,126 per night from Mar 10 to Mar 11
SAR 1,126
SAR 1,363 total
includes taxes & fees
10 Mar - 11 Mar
9.4/10 Exceptional! (332 reviews)
"Never disappoints!"

Reviewed on 2 March 2025

Inn at Perry Cabin
St Michaels Inn
St Michaels Inn
2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
Fully refundableReserve now, pay when you stay
The price is SAR 304 per night from Mar 20 to Mar 21
SAR 304
SAR 334 total
includes taxes & fees
20 Mar - 21 Mar
8/10 Very Good! (1,000 reviews)
Perfect little getaway for great price
"Great location, staff was so nice, friendly and accommodating! The room was clean, bathroom could use some updating and bed was really firm so be prepared. Pillow top would definitely be beneficial. Great morning coffee, and continental breakfast was ok. Loved that they provide bottle waters. I would ..."

Reviewed on 17 February 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 SAR 709 per night from Mar 5 to Mar 6
SAR 709
SAR 862 total
includes taxes & fees
5 Mar - 6 Mar
9.6/10 Exceptional! (298 reviews)
Perfect Get-away
"Beautiful hotel in a very convenient location near everything! Clean room and a very friendly staff."

Reviewed on 22 February 2025

The Wildset
See all 1,233 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 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.

Discover the most popular places to visit in St. Michaels

Chesapeake Bay Maritime Museum

Chesapeake Bay Maritime Museum

4.5/5(15 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.

Chesapeake Bay Maritime Museum

St. Michaels Winery

4.5/5(45 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.

St. Michaels Winery

1879 Hooper Straight Lighthouse

1879 Hooper Straight Lighthouse is just one of the places to see in St. Michaels, so why not enjoy the other things to explore during your travels? Stroll along the waterfront or visit the shops in this romantic area.

1879 Hooper Straight Lighthouse