St. Michaels Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in St. Michaels

St Michaels Inn
St Michaels Inn
2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
Fully refundable
The price is 3.181.711 ₫ per night from 1 Jul to 2 Jul
3.181.711 ₫
3.499.987 ₫ total
1 Jul - 2 Jul
includes taxes & fees
8/10 Very Good! (1,002 reviews)
"The hotel is near to the town of St. Michaels. It is reasonably priced. I have stayed at this hotel several times over the yrars. I think it is time for the hotel to be refurbished and updated."

Reviewed on 20 Jun 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 17.850.086 ₫ per night from 6 Jul to 7 Jul
17.850.086 ₫
21.598.578 ₫ total
6 Jul - 7 Jul
includes taxes & fees
9.4/10 Exceptional! (347 reviews)
"Beautiful white buildings surrounded by lush hydrangeas and immaculate gardens manicured meticulously. Our delux King room was extremely spacious and comfortable and lots of mirrors and great large towels. Cannot wait to go back."

Reviewed on 11 Jun 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 5.722.689 ₫ per night from 26 Jun to 27 Jun
5.722.689 ₫
6.869.840 ₫ total
26 Jun - 27 Jun
includes taxes & fees
9.6/10 Exceptional! (323 reviews)
"Great relatively new property in down St Michaels. Walkable to everything. On site restaurant Ruse was ver good. We’ll be back"

Reviewed on 10 Jun 2025

The Wildset
See all 1,280 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.

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.

Popular places to visit

Chesapeake Bay Maritime Museum

Chesapeake Bay Maritime Museum

You can study the exhibits at Chesapeake Bay Maritime Museum, a museum with a storied past, during your travels to St. Michaels. Stroll along the waterfront or experience the area's museums.

Chesapeake Bay Maritime Museum

St. Michaels Winery

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 Nature Trail

You can take time to visit St Michaels Nature Trail during your travels to St. Michaels. Stroll along this romantic area's waterfront or simply enjoy its seafood restaurants.

St Michaels Nature Trail