St. Michaels Vacations from $901

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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!

The Latest St. Michaels vacation packages

Price found within the past 48 hours. Click for updated prices.
Cayman Suites Hotel

Cayman Suites Hotel

2 out of 5
North Ocean City
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
7.6/10 Good! (1,003 reviews)
The coffee is good and the bed is good but the pillows are uncomfortable. The area really nice and the beach near of the place.

Reviewed on Aug 15, 2025

Sea Breeze Inn

Sea Breeze Inn

2 out of 5
Downtown Ocean City
Save 100% on your flight
per person
Sep 23 - Sep 28
found 17 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
6/10 (641 reviews)
2 minutes easy walk to the Boardwalk at the Gorgeous Beach

Reviewed on Jun 26, 2025

Sea Bay Hotel

Sea Bay Hotel

2.5 out of 5
Midtown Ocean City
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
8.2/10 Very Good! (495 reviews)
We stayed one night at Sea Bay Hotel — it was clean, comfortable, and a good experience.

Reviewed on Aug 14, 2025

Beach Walk

Beach Walk

2 out of 5
Downtown Ocean City
Save 100% on your flight
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
7.8/10 Good! (77 reviews)
Shower was very tiny. No place to sit in room other than bed.

Reviewed on Aug 3, 2025

Kokomo Suites

Kokomo Suites

2.5 out of 5
North Ocean City
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
7.6/10 Good! (323 reviews)
The hotel is not completely remodeled. We stayed on the second floor. The bathroom was old and worn. However, the room was clean and there’s a lot of space. There are full size beds, not queens. The pool was very nice and they have plenty of parking. Overall, the place rates “good”.

Reviewed on Aug 14, 2025

Don't see what you're looking for?
See all available trips from Columbus to St. Michaels
View all trips

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

St. Michaels Museum

You can browse the exhibits at St. Michaels Museum, a museum with a storied past, during your trip to St. Michaels. Discover the seafood restaurants and its museums while you're in the area.

St. Michaels Museum

St. Michaels Hotel Deals

St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
Fully refundable
$100 nightly
The price is $111 total per night from Sep 1 to Sep 2
$111 total
Sep 1 - Sep 2
Total includes taxes and fees
8/10 Very Good! (1,001 reviews)
"Very nice stay"

Reviewed on Aug 13, 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
$235 nightly
The price is $259 total per night from Aug 18 to Aug 19
$259 total
Aug 18 - Aug 19
Total includes taxes and fees
9.6/10 Exceptional! (356 reviews)
"The room was stark, no artwork, flowers or anything warm and inviting. A shelf in the bathroom for guests' personal toiletries is badly needed as well."

Reviewed on Aug 13, 2025

The Wildset
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln, St. Michaels, MD
$610 nightly
The price is $671 total per night from Aug 24 to Aug 25
$671 total
Aug 24 - Aug 25
Total includes taxes and fees
9.4/10 Exceptional! (358 reviews)
"Love the cozy vibe & beautiful landscape"

Reviewed on Aug 8, 2025

Inn at Perry Cabin
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.

Things to do in and around St. Michaels

St. Michaels, Maryland, is perfect for outdoor, romantic, and family vacations. Visitors can enjoy the scenic boardwalk and recreational areas, as well as exciting activities like boat tours, sailing adventures, and private tours. Don't miss out on the enchanting sunset cruises that showcase the beauty of this charming town. Explore St. Michaels for a delightful getaway filled with memorable experiences.

Shopping

In St. Michaels, explore the charming Saint Michaels Village, perfect for gifts with a family-friendly vibe. If you're up for a drive, visit the Queenstown Premium Outlets 14 miles away for a variety of brand-name bargains, or check out Easton Cycle and Sport, located 9 miles away.

Recreation

At Avalon Theatre, enjoy a captivating performance in a charming atmosphere that blends culture and romance. Hog Neck Golf Course offers a scenic outdoor experience for golf enthusiasts. For ultimate relaxation, Talbot Massage provides soothing body treatments designed to rejuvenate your mind and body.

Adventure

Experience the thrills at Chesapeake Beach Water Park, located 18 miles from St. Michaels, featuring exciting water slides and family-friendly attractions. For outdoor adventure, try the Annapolis Sailing School, also 18 miles away, where you can learn to sail and enjoy the beautiful waters.

For a fun indoor adventure, head to Annapolis Bowl, located 23 miles from St. Michaels, where you can enjoy bowling and arcade games in a lively atmosphere perfect for families.

Nightlife

St. Michaels offers a charming nightlife with venues like the lively Town Dock Restaurant, perfect for waterfront dining and drinks. For a laid-back vibe, visit the St. Michaels Winery, where you can enjoy tastings and local music in a cozy setting.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Tips to save on your trip to St. Michaels

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling to St. Michaels during the low season (January to March) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a St. Michaels vacation package cost?
You can snap up a vacation package to this destination from $901 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?
You can typically find lower prices and greater availability in January, September and December. Browse our cheap St. Michaels vacation packages and you could land some excellent off-season deals.
How many days is enough for St. Michaels?
The ideal duration of your St. Michaels vacation depends on what you'd like to do. Generally, a handful of days to a week will give you enough time to go to all the main sights and discover some hidden spots along the way.
Is it worth booking a vacation package to St. Michaels?
St. Michaels has all the ingredients you need for a fantastic trip — nature, culture and watersports are just the start. Whether you want to visit attractions like Chesapeake Bay Maritime Museum and St. Michaels Museum, or take the path less traveled, you'll have plenty to do on your St. Michaels vacation.
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.
Does Expedia offer Book Now, Pay Later St. Michaels vacation packages?
Set off on your ideal getaway to St. Michaels with help from Expedia's Book Now, Pay Later vacations. There's no need to save up or wait until your next paycheck — we've teamed up with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans let you spread the total cost over 3, 6 or 12 months. With no hidden charges or late payment fees, you can easily budget for your trip and snap up cheap deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.