St. Michaels Vacations from $864

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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.
Empress Motel

Empress Motel

2 out of 5
Downtown Ocean City
Price was $1,086, price is now $864 per person
$864
per person
Oct 2 - Oct 6
found 3 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Salisbury (SBY)
7.8/10 Good! (122 reviews)
Room smelled like mold

Reviewed on Aug 23, 2025

Sahara Motel

Sahara Motel

2.5 out of 5
Downtown Ocean City
Price was $1,220, price is now $885 per person
$885
per person
Oct 2 - Oct 6
found 3 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Salisbury (SBY)
7.8/10 Good! (385 reviews)
Was no toilet paper holder in bathroom

Reviewed on Aug 23, 2025

Ocean Terrace Family Apartments

Ocean Terrace Family Apartments

3 out of 5
Downtown Ocean City
Save 100% on your flight
Price was $1,948, price is now $1,444 per person
$1,444
per person
Oct 2 - Oct 6
found 3 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Salisbury (SBY)
8.4/10 Very Good! (28 reviews)
The unit was outdated, small, and had mismatched and old furniture. The shower in one of our bathrooms wouldn’t drain. The oven did not work. There was only one television. Concerns couldn’t be communicated because the staff hardly spoke English (although they were very nice). The unit was in a really nice location - 1.5 blocks from the boardwalk and beach. We liked the outside showers.

Reviewed on Aug 9, 2025

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was $1,574, price is now $1,199 per person
$1,199
per person
Oct 2 - Oct 6
found 3 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Salisbury (SBY)
9/10 Wonderful! (3,117 reviews)
Great room, great location, great service!

Reviewed on Aug 23, 2025

Beach Walk

Beach Walk

2 out of 5
Downtown Ocean City
Price was $1,478, price is now $1,141 per person
$1,141
per person
Oct 2 - Oct 6
found 3 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Salisbury (SBY)
7.6/10 Good! (81 reviews)
We love the location and price. It’s the only place I’ve seen so far that has nearly ocean front view from the porch without paying ocean front prices. It’s small, quaint, and safe feeling. Very friendly staff. It has some shortcomings that would be easy to rectify, such as no handles on the cupboards and drawers (at least in family room #18), we had to make tape handles to be able to open cupboards. The fridge had its handle broken off, light bulbs were burnt out, lots of dirt where the floor meets the walls, the carpet is very greasy and stained, mini blinds are messed up. These things could bother someone with higher expectations. But for us, the only thing that really bothered us was that even though it has a kitchenette, it is completely bare…. no utensils or dishes. They really should specify this in their description of the room. Even when I called the hotel to ask I was told “I don’t know if there’s silverware in there.”. If they put a little more effort into its upkeep it would be absolutely perfect. But we come every year and will continue to do so, we love it despite its imperfections.

Reviewed on Aug 16, 2025

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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

The Wildset

The Wildset

2.5 out of 5
209 N Talbot St, St. Michaels, MD
$235 nightly
The price is $259 total per night from Aug 26 to Aug 27
$259 total
Aug 26 - Aug 27
Total with taxes and fees
9.6/10 Exceptional! (361 reviews)
"Our room was lovely and exactly as described online. Loved the complementary snacks. Breakfast was delicious. We were particularly impressed with the guest services. Everyone was gracious, helpful, and welcoming. Dining at Ruse is a must!! Make reservations in advance. The food and service are ..."

Reviewed on Aug 15, 2025

The Wildset
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln, St. Michaels, MD
$629 nightly
The price is $692 total per night from Sep 4 to Sep 5
$692 total
Sep 4 - Sep 5
Total with taxes and fees
9.4/10 Exceptional! (360 reviews)
"IPC is a "hidden gem." It was great, from "soup to nuts." Especially the staff, who were all friendly, polite, knowledgeable, flexible, and helpful. Thanks to all of them on our behalf, please: staff are what make all the difference at any resort. (SPA treatments are a must.) Just one suggestion: ..."

Reviewed on Aug 14, 2025

Inn at Perry Cabin
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
Fully refundable
$87 nightly
The price is $96 total per night from Sep 1 to Sep 2
$96 total
Sep 1 - Sep 2
Total with taxes and fees
8/10 Very Good! (1,002 reviews)
"This may sound like a backhanded compliment, but there was nothing spectacular about this hotel. However, everything about it was very very, very good! And sometimes, that's perfect! The hospitality was exceptional, complementary breakfast was outstanding, and the pool is in better condition than ..."

Reviewed on Aug 18, 2025

St Michaels Inn
See all 1,292 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.

Find the best attractions in and around St. Michaels

St. Michaels, Maryland, is perfect for outdoor enthusiasts and families, offering a charming blend of romantic getaways and cultural experiences. Explore the local marina, visit the historical museum, and enjoy the scenic urban park. The nearby Miles River adds to the area's allure, making it an ideal destination for travelers seeking adventure and relaxation in a picturesque setting.

  • Chesapeake Bay Maritime Museum: Immerse yourself in the rich maritime history of the Chesapeake Bay at this engaging museum. Explore historic vessels, interactive exhibits, and picturesque waterfront views that celebrate the region's culture and maritime heritage.
  • St. Michaels Museum: Delve into the local history at St. Michaels Museum, where you can discover artifacts and stories that highlight the town's past. The museum's charming setting offers a glimpse into the lives of those who shaped this unique community.
  • Pickering Creek Audubon Center: Experience nature at its finest at this eco-friendly center located 7 miles from St. Michaels. With trails, wildlife observation areas, and educational programs, it’s a haven for birdwatchers and outdoor enthusiasts alike.

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.

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Frequently asked questions

How much does a St. Michaels vacation package cost?
You can snap up a vacation package to this destination from $864 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.