St. Michaels Vacations from $318

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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.
Ashore Resort & Beach Club

Ashore Resort & Beach Club

3.5 out of 5
North Ocean City
Save 100% on your flight
per person
May 30 - Jun 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
8.2/10 Very Good! (1,107 reviews)
The dining place was very poor communication and poor selection of food and drinks.

Reviewed on Apr 25, 2025

Boardwalk One

Boardwalk One

3 out of 5
Downtown Ocean City
Save 100% on your flight
per person
Jul 12 - Jul 17
found 18 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
7.2/10 Good! (143 reviews)
Rooms are huge and have everything you need.

Reviewed on Sep 18, 2023

Club Ocean Villas II

Club Ocean Villas II

3.5 out of 5
North Ocean City
Save 100% on your flight
per person
Jul 15 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Salisbury (SBY)
8.8/10 Excellent! (53 reviews)
2nd floor apartment, clean and very cold upon arrival. It was too cold that the central air vents were condensating too much. The apartment is 1 block away from the beach ⛱️. Very close to CVS, Wawa, and Food Lion supermarket. Also, Starbucks, Mcdonald, and other restaurants. Basic amenities provided in the unit and in kitchen. Towels provided needed another washing. Washer and dryer provided in the unit. Outside deck with chairs and umbrella provided to sit outside. Living Room furniture is adequate but needs a steam cleaning. TVs in all the rooms functional. The plants at the entrance need to be trimmed it's an annoyance.

Reviewed on Jul 29, 2024

Monte Carlo Boardwalk Oceanfront Ocean City

Monte Carlo Boardwalk Oceanfront Ocean City

3 out of 5
Downtown Ocean City
Save 100% on your flight
per person
May 30 - Jun 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
7.8/10 Good! (1,001 reviews)
I thought this property worked out great for a short family getway trip and thought the staff was very friendly. The only thing I was not a fan of was the parking options, no gym and no breakfast.

Reviewed on Apr 25, 2025

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Save 100% on your flight
per person
May 30 - Jun 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
9/10 Wonderful! (2,643 reviews)
Everything was wonderful

Reviewed on Apr 25, 2025

Find the Best St. Michaels Vacation Packages

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

Ready to book your vacation to St. Michaels?

 

Choose your dates

St. Michaels Hotel Deals

Inn at Perry Cabin
Inn at Perry Cabin
5 out of 5
308 Watkins Ln, St. Michaels, MD
The price is $604 per night from May 4 to May 5
$604
includes taxes & fees
$549 per night
May 4 - May 5
9.4/10 Exceptional! (343 reviews)
"Peaceful and great views !"

Reviewed on Apr 22, 2025

Inn at Perry Cabin
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 $119 per night from May 8 to May 9
$119
includes taxes & fees
$108 per night
May 8 - May 9
8/10 Very Good! (1,002 reviews)
"Nice, very clean clean, safe and peaceful place to stay when visiting St. Michael’s. Highly recommend."

Reviewed on Apr 21, 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
The price is $263 per night from Apr 28 to Apr 29
$263
includes taxes & fees
$239 per night
Apr 28 - Apr 29
9.6/10 Exceptional! (309 reviews)
"We loved staying here and would recommend this hotel to anyone. It was so clean, convenient to all the shops,and restaurants and we loved all the little touches like breakfast, the bikes, and the nightly s'mores."

Reviewed on Apr 15, 2025

The Wildset
See all 1,235 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.

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 $318 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.

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

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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.