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
SAR 314
SAR 346 total
31 Aug - 1 Sep
includes taxes & fees
8/10 Very Good! (1,011 reviews)
"The rooms, though dated, are clean. I did bring to the attention of the manager that the towel bar in my bathroom was coming off. The handrail to walk down the steps into the pool was also loose, which I think is a safety hazard. The manager acknowledged he knew about it, but despite tons of cosmetic ..."
Reviewed on 28 August 2026
Inn at Perry Cabin
308 Watkins Ln St. Michaels MD
SAR 1,811
SAR 1,992 total
23 Sep - 24 Sep
includes taxes & fees
The Wildset
209 N Talbot St St. Michaels MD
Fully refundableReserve now, pay when you stay
SAR 897
SAR 1,081 total
23 Sep - 24 Sep
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.
St. Michaels Marina
Explore the waterfront in St. Michaels with a trip to St. Michaels Marina.
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 Nature Trail
You can take time to visit St Michaels Nature Trail during your travels to St. Michaels.
Saint Michaels Town Hall
Located in the St. Michaels Historic District, this town hall adds charm to the area's preserved 19th-century architecture. Explore the surrounding brick sidewalks while discovering the town's rich maritime heritage.
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 travelers.
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 traveling 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.
