St. Michaels Vacations
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Find the Best St. Michaels Vacation Packages
St. Michaels Hotel Deals
St Michaels Inn
1228 S Talbot Street St. Michaels MD
Fully refundableReserve now, pay when you stay
NT$2,841
NT$3,125 total
Oct 19 - Oct 20
includes taxes & fees
8/10 Very Good! (1,001 reviews)
"When booking using the word "Inn" at St. Michaels, I assumed the property would have more of a warm bed and breakfast feel. It was actually a motor lodge/motel feel. The staff was amazing."
Reviewed on 2026/10/8
Inn at Perry Cabin
308 Watkins Ln St. Michaels MD
NT$16,385
NT$18,023 total
Nov 8 - Nov 9
includes taxes & fees
9.6/10 Exceptional! (405 reviews)
"Outstanding experience in every way. Staff was superior — everyone greeted us by name and was eager to ensure we had everything we needed. Meals at Stars were excellent — and the gorgeous views of the water and property enhanced the dining experience. The lit firepits and comfy seating outside were ..."
Reviewed on 2026/9/29
The Wildset
209 N Talbot St St. Michaels MD
Fully refundableReserve now, pay when you stay
NT$7,314
NT$8,844 total
Nov 3 - Nov 4
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)
Explore maritime heritage at this waterfront museum featuring the historic Hooper Strait Lighthouse and indigenous Chesapeake Bay watercraft. Watch shipwrights craft vessels while enjoying Miles River views.
Saint Michaels Village
This historic waterfront town showcases Maryland's maritime heritage through preserved colonial architecture. Explore the Maritime Museum or enjoy fresh seafood while watching sailboats glide across the harbor.
St. Michaels Winery
8.6/10 (91 reviews)
Sample the Eastern Shore's finest wines in this historic Old Mill District winery. Enjoy guided tastings of 18 handcrafted varieties while learning about Maryland's unique terroir.
1879 Hooper Straight Lighthouse
This rare screwpile lighthouse, relocated from Chesapeake Bay, offers a glimpse into 19th-century maritime life. Climb the spiral staircase to the lantern room for sweeping bay views and authentic keeper's quarters.
Perry Cabin Park
This 9.5-acre community space offers well-maintained sports fields and a playground for active recreation. Enjoy a peaceful picnic in the pavilion or join a local baseball game in this serene St. Michaels gathering spot.
St. Michaels Museum
8.6/10 (9 reviews)
Step into three restored 19th-century buildings that reveal the rich history of this Chesapeake Bay town. Explore exhibits on Frederick Douglass's local connections through walking tours of historic St. Michaels.
Windon Distilling
LYON RUM crafts small-batch American spirits in a historic St. Michaels mill using traditional methods. Sample their handcrafted rums in the welcoming tasting room while learning about their cane-to-glass process.
St Michaels Nature Trail
You can take time to visit St Michaels Nature Trail during your travels to St. Michaels.
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?
- 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.
- 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.
- 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.
- 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.
