St. Michaels Holidays

  • Plan, book, travel with confidence
    • payments icon
    Better together
    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

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 S$127 per night from 16 Dec to 17 Dec
S$127
includes taxes & fees
16 Dec - 17 Dec
8/10 Very Good! (1,003 reviews)
"This property is not fancy but it is a very good value. Rooms could use a little face lift but everything is clean, functional and useable. Mattress was excellent; TV only 24 inches but OK. Breakfast was fine."

Reviewed on 22 Nov,2024

St Michaels Inn
Inn at Perry Cabin
Inn at Perry Cabin
5 out of 5
308 Watkins Ln, St. Michaels, MD
The price is S$467 per night from 17 Dec to 18 Dec
S$467
includes taxes & fees
17 Dec - 18 Dec
9.4/10 Exceptional! (322 reviews)
"Everything about this property was exceptional! Definitely will be back!"

Reviewed on 10 Nov,2024

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$324 per night from 25 Nov to 26 Nov
S$324
includes taxes & fees
25 Nov - 26 Nov
9.6/10 Exceptional! (283 reviews)
"I loved the quiet charm of the hotel along with the modern amenities. The staff were all very kind, helpful, and professional."

Reviewed on 18 Nov,2024

The Wildset
See all 1,228 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?
From as low as . Yes, you read that right. Our St. Michaels packages are the best way to make your budget stretch further. Combine your flights, hotels and rental car and get to know this wonderful destination.
How do I get a cheap travel package to St. Michaels?
Combine your bookings with Expedia to save on your next trip. With over 550 airlines and 1,000,000 hotel options globally, your St. Michaels holiday package can be customized exactly to suit your travel style. With all that extra money, why not add some exciting experiences and tours? It’s an easy way to unlock even more savings. That dream holiday to St. Michaels is much closer than you thought!
Where should I stay in St. Michaels?
We recommend staying near the action. Many people like to book hotels within easy reach of popular sights, such as St. Michaels Winery, Chesapeake Bay Maritime Museum and St. Michaels Museum.
What are the top hotels in St. Michaels?
If it’s your first visit to St. Michaels, reserve a room at Dollhouse In Central Historic St Michaels or The Wildset. Both will make you feel at home and are popular options with many savvy travellers.
How far in advance should I book my St. Michaels holiday?
It can be hard to know exactly when is the perfect time to book your St. Michaels holiday. But typically the earlier you book, the lower the prices. Sometimes, you can lock in your flights and hotels nearly 12 months prior to your departure date. If you’re thinking of a last-minute getaway, no need to worry! There are plenty of fantastic deals announced on Expedia all the time.
What does an Expedia St. Michaels travel package include?
Hotels, flights and car rentals — we bring you all the best deals. All you have to do is figure out your favourite combination. Once you’ve made your booking, you can add on the fun stuff like activities and sightseeing tours. Our travel packages make it easy to customize an exciting St. Michaels trip.
What should I know before booking a St. Michaels travel package?
Get set to save with an Expedia travel package. Bundle your flights, rental cars and hotels and be rewarded with terrific discounts. You’re not limited to hotels, though. Book with us and select from beachfront villas, rural cottages and even ranches and treehouses!
Can I choose my airline with a St. Michaels Expedia holiday package?
The choice is all yours! We offer more than 550 airlines all over the world, so you can design your St. Michaels holiday according to your budget and travel needs.
If I'm not able to travel, can I cancel my St. Michaels holiday package?
Because we understand life can be unpredictable, the answer is yes. For further details, head to our Customer Service Portal. But generally speaking, if you’ve booked your St. Michaels holiday package in the last 24 hours, you may be able to cancel or change it for no charge. Your airline, hotel or car rental company may charge a fee if your booking is older than that.

* 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.