St. Michaels Vacations from $240

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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.
Gold Leaf Hotel of Dewey - Rehoboth Beach

Gold Leaf Hotel of Dewey - Rehoboth Beach

2.5 out of 5
Price was $263, price is now $240 per person
$240
per person
Jan 9 - Jan 11
found 7 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Salisbury (SBY)
8.8/10 Excellent! (1,014 reviews)
Little old and dated couch was very uncomfortable but price is right and very friendly but could be little cleaner and updated

Reviewed on Oct 12, 2025

Bethany Beach Ocean Suites Residence Inn by Marriott

Bethany Beach Ocean Suites Residence Inn by Marriott

3 out of 5
Downtown Bethany Beach
Price was $409, price is now $333 per person
$333
per person
Jan 9 - Jan 11
found 7 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Salisbury (SBY)
9/10 Wonderful! (763 reviews)
Bugs on window sill in dining area. Grease trap on sidewalk was leaking. All other public areas were EXCELLENT. Housekeeping could have cleaned the toilet . Greeter in load/unload area was very helpful and pleasant. I think his name was Olem. Front desk staff was pleasant and friendly and knowledgeable. Overall we have no complaints. We had a pleasant stay.

Reviewed on Oct 1, 2025

Atlantic Oceanside Dewey

Atlantic Oceanside Dewey

2.5 out of 5
Price was $595, price is now $529 per person
$529
per person
Jan 9 - Jan 11
found 7 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Salisbury (SBY)
8/10 Very Good! (971 reviews)
Room was ok. Great location. One issue, you have to pay to park at the hotel? Was unaware of this since none of the othe hotels in the area do this. So when shopping around, the rate looks lower than what it really is. Seems a little shady.

Reviewed on Oct 12, 2025

Hyatt Place Dewey Beach

Hyatt Place Dewey Beach

3 out of 5
Price was $318, price is now $287 per person
$287
per person
Jan 9 - Jan 11
found 7 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Salisbury (SBY)
8.8/10 Excellent! (1,001 reviews)
Room needed work bathroom door would not close

Reviewed on Oct 18, 2025

Residence Inn by Marriott Ocean City

Residence Inn by Marriott Ocean City

3 out of 5
Midtown Ocean City
Price was $309, price is now $281 per person
$281
per person
Jan 9 - Jan 11
found 7 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Salisbury (SBY)
9/10 Wonderful! (1,002 reviews)
Especially the staff everyone was so nice so polite and so helpful when we had an emergency they were right there to help us the lady at the front desk. Paula was extremely helpful to us getting our dinner cooked and it turned out to be an awesome fun relaxing trip mostly due to the staff of this facility they were awesome. I would recommend it to anyone that has headed that way.

Reviewed on Oct 18, 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

St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
Fully refundable
$93 nightly
The price is $103 total per night from Oct 22 to Oct 23
$103 total
Oct 22 - Oct 23
Total with taxes and fees
8/10 Very Good! (1,002 reviews)
"Basic room, clean and comfortable. Only complaint, it took 15 minutes to get hot water in the shower -- wasted a lot of water waiting. Good TV selection, too."

Reviewed on Oct 17, 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
$239 nightly
The price is $263 total per night from Oct 28 to Oct 29
$263 total
Oct 28 - Oct 29
Total with taxes and fees
9.6/10 Exceptional! (391 reviews)
"Lovely property and friendly attentive staff. Appreciated the text updates with info and reminders of service options. Enjoyed the complimentary breakfast and smore option in the evenings. The ruse restaurant was also fantastic, had dinner there our first evening and thoroughly enjoyed it. The unique ..."

Reviewed on Oct 12, 2025

The Wildset
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln, St. Michaels, MD
$400 nightly
The price is $440 total per night from Nov 17 to Nov 18
$440 total
Nov 17 - Nov 18
Total with taxes and fees
9.4/10 Exceptional! (366 reviews)
"Staff is outstanding in every aspect. Add upgrades to rooms in furniture and painting, add sugar free syrup and pancakes for breakfast. Tours and Toast were lovely."

Reviewed on Oct 17, 2025

Inn at Perry Cabin
See all 1,296 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.

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

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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 $240 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.

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