St. Michaels Vacations from $837

Book a Hotel + Flight or Car together to unlock savings

Choose one or more items to build your trip:
    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to $580 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

Food, history, entertainment and more … There's a whole lot to discover with a St. Michaels vacation package. And with the ability to easily customize your city getaway, you know it'll be one that's difficult to forget. A trip to St. Michaels is a wonderful opportunity to go sightseeing. Make sure you visit popular attractions like St. Michaels Winery, Chesapeake Bay Maritime Museum and St. Michaels Museum. Stop dreaming and start doing. Explore the wide range of options on Expedia today and put your St. Michaels vacation plans into gear!

The Latest St. Michaels Vacation Packages

Ashore Resort & Beach Club

Ashore Resort & Beach Club

3.5 out of 5
North Ocean City
per person
May 24 - May 27
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
8.2/10 Very Good! (230 reviews)
Hôtel is in good condition the room is clean, they have plenty of parking. The staff were not very friendly, they forgot to provide us with sheets for the sofa bed but they brought them up upon request but then we realized they didn’t provide additional pillows. The bath wash bottle was empty. I understand that most missing item could be replaced with a phone call to front desk but it’s Anoying that we have to reach out they should inspect the room before assigning it to guest.

Reviewed on Apr 16, 2024

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
per person
Jul 11 - Jul 14
Roundtrip non-stop flight included
Detroit (DTW) to Salisbury (SBY)
8.8/10 Excellent! (1,987 reviews)
Your have a view of the broadwalk and beach ⛱️

Reviewed on Apr 19, 2024

Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
North Ocean City
per person
May 24 - May 27
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
7.8/10 Good! (1,815 reviews)
Everything was great !

Reviewed on Apr 15, 2024

The Americana Hotel

The Americana Hotel

2.5 out of 5
Downtown Ocean City
per person
Jul 7 - Jul 11
Roundtrip non-stop flight included
Detroit (DTW) to Salisbury (SBY)
8.4/10 Very Good! (1,003 reviews)
I stayed there for a convention last weekend April 12-14th 2024 and I was amazed how clean and peaceful this hotel was. I really enjoyed my stay here and I’m definitely booking for next years convention. You get a 5 star for me

Reviewed on Apr 18, 2024

Flamingo Motel

Flamingo Motel

2 out of 5
Midtown Ocean City
per person
Jul 7 - Jul 11
Roundtrip non-stop flight included
Detroit (DTW) to Salisbury (SBY)
7.6/10 Good! (909 reviews)
It was quite and it was a nice view of the beach

Reviewed on Apr 1, 2024

Prices and availability subject to change. Additional terms may apply.

St. Michaels Essential Information

Language
English
Currency
U.S dollars
Population
1,050
Max Temp Winter
45ºF
Max Temp Summer
80ºF
Top Sights
St. Michaels Winery, Avalon Theatre and Historical Society of Talbot County

St. Michaels Hotel Deals

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 $108 per night from May 1 to May 2
$108
per night
May 1 - May 2
8/10 Very Good! (1,001 reviews)
"Very clean, staff was very helpful and friendly!"

Reviewed on Apr 16, 2024

St Michaels Inn
Inn at Perry Cabin
Inn at Perry Cabin
5 out of 5
308 Watkins Ln, St. Michaels, MD
The price is $493 per night from Apr 21 to Apr 22
$493
per night
Apr 21 - Apr 22
9.4/10 Exceptional! (292 reviews)
"The room was clean and quaint. The bed was comfortable. The staff were friendly and helpful."

Reviewed on Feb 25, 2024

Inn at Perry Cabin
The Wildset
The Wildset
2.5 out of 5
209 N Talbot St, St. Michaels, MD
The price is $249 per night from Apr 21 to Apr 22
$249
per night
Apr 21 - Apr 22
9.6/10 Exceptional! (219 reviews)
Great time
"It was a clean and trendy lodging"

Reviewed on Apr 3, 2024

The Wildset
See all 1,219 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.

Explore other types of vacation packages

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?
From as low as $837. Yes, you read that right. Our St. Michaels packages are the best way to make your budget stretch further. Combine your flights, hotels and rental car and get to know this wonderful destination.
How do I get a cheap travel package to St. Michaels?
Combine your bookings with Expedia to save on your next trip. With over 550 airlines and 1,000,000 hotel options globally, your St. Michaels vacation package can be customized exactly to suit your travel style. With all that extra money, why not add some exciting experiences and tours? It’s an easy way to unlock even more savings. That dream vacation to St. Michaels is much closer than you thought!
Where should I stay in St. Michaels?
We recommend staying near the action. Many people like to book hotels within easy reach of popular sights, such as St. Michaels Winery, Chesapeake Bay Maritime Museum and St. Michaels Museum.
What are the top hotels in St. Michaels?
If it’s your first visit to St. Michaels, reserve a room at Dollhouse In Central Historic St Michaels or The Wildset. Both will make you feel at home and are popular options with many savvy travelers.
How far in advance should I book my St. Michaels vacation?
It can be hard to know exactly when is the perfect time to book your St. Michaels vacation. But typically the earlier you book, the lower the prices. Sometimes, you can lock in your flights and hotels nearly 12 months prior to your departure date. If you’re thinking of a last-minute getaway, no need to worry! There are plenty of fantastic deals announced on Expedia all the time.
What does an Expedia St. Michaels travel package include?
Hotels, flights and car rentals — we bring you all the best deals. All you have to do is figure out your favorite combination. Once you’ve made your booking, you can add on the fun stuff like activities and sightseeing tours. Our travel packages make it easy to customize an exciting St. Michaels trip.
What should I know before booking a St. Michaels travel package?
Get set to save with an Expedia travel package. Bundle your flights, rental cars and hotels and be rewarded with terrific discounts. You’re not limited to hotels, though. Book with us and select from beachfront villas, rural cottages and even ranches and treehouses!
Can I choose my airline with a St. Michaels Expedia vacation package?
The choice is all yours! We offer more than 550 airlines all over the world, so you can design your St. Michaels vacation according to your budget and travel needs.
If I'm not able to travel, can I cancel my St. Michaels vacation package?
Because we understand life can be unpredictable, the answer is yes. For further details, head to our Customer Service Portal. But generally speaking, if you’ve booked your St. Michaels vacation package in the last 24 hours, you may be able to cancel or change it for no charge. Your airline, hotel or car rental company may charge a fee if your booking is older than that.

Discover the most popular places to visit in St. Michaels

Image for 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
Image for St. Michaels Winery

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
Image for St. Michaels Museum

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

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.