St. Michaels Holidays

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Your St. Michaels Holiday

With a St. Michaels holiday package, say goodbye to endless planning and hello to trouble-free adventure. Every detail of your escape has been taken care of before you go, so you can get on with experiencing this fantastic city. Every trip to St. Michaels needs a well-crafted itinerary. Fill yours with big-name attractions like St. Michaels Winery, Chesapeake Bay Maritime Museum and St. Michaels Museum. Your ideal St. Michaels holiday is only clicks away. Explore flights, hotels and more on Expedia for an adventure that's tailored just for you.

St. Michaels Holiday

St. Michaels Essential Information

Language
English
Currency
U.S dollars
Population
1,050
Max Temp Winter
7ºC
Max Temp Summer
27ºC
Top Sights
St. Michaels Winery, Avalon Theatre and St. Michaels Museum

Our pick of the best St. Michaels Hotel Deals

St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
Fully refundable
The price is AU$185 per night from 4 Aug to 5 Aug
AU$185
4 Aug - 5 Aug
includes taxes & fees
8/10 Very Good! (1,001 reviews)
Good choice for us
"Overall we felt the room was clean , comfortable, and quiet. We used the pool and enjoyed the exercise and opportunity to meet and chat with other guests. The service was accommodating and friendly. We definitely would chose this hotel again."

Reviewed on 30 Jul. 2025

St Michaels Inn
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln, St. Michaels, MD
The price is AU$1,158 per night from 28 Aug to 29 Aug
AU$1,158
28 Aug - 29 Aug
includes taxes & fees
9.4/10 Exceptional! (355 reviews)
"The setting is spectacular and the staff could not have been kinder and more helpful."

Reviewed on 13 Jul. 2025

Inn at Perry Cabin
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 AU$371 per night from 18 Aug to 19 Aug
AU$371
18 Aug - 19 Aug
includes taxes & fees
9.6/10 Exceptional! (345 reviews)
Generous people and place
"Perfect from arrival to departure. We did happy hour at the restaurant which was high value and delicious. They also have a luxurious garden fire pit and smores experience included during summer. Continental breakfast also included. It’s such a well-run, generous experience that reminds me of Sonoma ..."

Reviewed on 27 Jul. 2025

The Wildset
See all 1,281 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 Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a St. Michaels holiday package cost?
You can snap up a holiday package to this destination on Expedia. However, how much your holiday 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?
January, February and March are great times to search for cheap St. Michaels holiday packages. Travelling in quieter periods means you can typically find better prices on accommodation and flights.
How many days is enough for St. Michaels?
With a well-organised travel plan, you can easily visit the main St. Michaels sights in a handful of days. But if you want to venture off the beaten track or go on day tours, consider booking your St. Michaels holiday for longer.
Is it worth booking a holiday package to St. Michaels?
Well known for its watersports, culture and nature, a St. Michaels holiday is a hit with all kinds of travellers. Be sure to check out key sights like Chesapeake Bay Maritime Museum and St. Michaels Museum, and consider renting a set of wheels for day trips to experience even more.
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 holiday package as soon as possible.
Is it cheaper to book a St. Michaels holiday as a package?
You can enjoy significant savings on your next St. Michaels escape by booking a tailored holiday 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 holiday 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.
How to plan a trip to St. Michaels?

  1. Choose when to get away: Check your diary and get packing. Your favourite season and the available activities will also help you decide when to escape to St. Michaels.
  2. Plan your budget wisely: As well as the price of your hotel, you'll need to factor in other expenses. These include transportation, flights and food. Also, set aside some extra funds for unexpected expenses that may arise during your trip to St. Michaels.
  3. Set the duration of your trip: Start by compiling a list of the activities and sights you want to get to in St. Michaels. Then, estimate how long you'll need for each, including any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a personalised St. Michaels holiday package.

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