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 refundableReserve now, pay when you stay
The price is 2.575.615 ₫ per night from 21 Jul to 22 Jul
2.575.615 ₫
2.833.177 ₫ total
21 Jul - 22 Jul
includes taxes & fees
8.2/10 Very good! (1,001 reviews)
"This is not an Inn, it is a motel with rooms opening to parking lot. Rooms could use maintenance - the ac unit was incredibly loud, paint was peeling, a crack in outer door, dirty corners. Breakfast was ample and very good."

Reviewed on 14 Jul 2026

St Michaels Inn
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln St. Michaels MD
The price is 17.485.830 ₫ per night from 2 Aug to 3 Aug
17.485.830 ₫
19.234.413 ₫ total
2 Aug - 3 Aug
includes taxes & fees
9.6/10 Exceptional! (391 reviews)
"Staff were awesome, location is awesome. Best place to stay in St. Michael's."

Reviewed on 27 Jun 2026

Inn at Perry Cabin
The Wildset

The Wildset

2.5 out of 5
209 N Talbot St St. Michaels MD
The price is 6.274.945 ₫ per night from 11 Aug to 12 Aug
6.274.945 ₫
7.558.815 ₫ total
11 Aug - 12 Aug
includes taxes & fees
9.8/10 Exceptional! (475 reviews)
"Rooms nice. Breakfast was ok. Quiche was cold. Should have been kept hot. Good location. Staff very nice and helpful."

Reviewed on 13 Jul 2026

The Wildset
See all 1,265 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.

Stay near popular St. Michaels attractions

A lighthouse on stilts with a green roof, surrounded by water and greenery.
Photo by Louise Johnson
Open Photo by Louise Johnson

Chesapeake Bay Maritime Museum

9.4/10 (91 reviews)
Explore maritime heritage at this waterfront museum featuring the historic Hooper Strait Lighthouse and indigenous Chesapeake Bay watercraft. Watch shipwrights craft vessels while enjoying Miles River views.
See properties

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.

Explore a world of travel with Expedia