St. Michaels Holidays

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Top hotels in St. Michaels

Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln, St. Michaels, MD
The price is S$892 per night from 1 Sept to 2 Sept
S$892
1 Sept - 2 Sept
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 S$308 per night from 19 Aug to 20 Aug
S$308
19 Aug - 20 Aug
includes taxes & fees
9.6/10 Exceptional! (346 reviews)
"Site was exactly as advertised. The team was very responsive, and the service at breakfast wonderful. My only complaint would be the excessive (in my opinion) property lighting all through the night."

Reviewed on 31 Jul, 2025

The Wildset
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
Fully refundable
The price is S$133 per night from 1 Sept to 2 Sept
S$133
1 Sept - 2 Sept
includes taxes & fees
8/10 Very Good! (1,002 reviews)
Great place to stay!
"Loved everything about this stay from the friendly staff, comfortable room and pristine pool. Enjoyed the continental breakfast each morning. Close to restaurants and shopping. A lovely outside area where we enjoyed the music of the mockingbirds. Anyone visiting St. Michaels should consider a stay ..."

Reviewed on 31 Jul, 2025

St Michaels Inn
See all 1,286 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.