Talbot County Holidays
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Top destinations in Talbot County
St. Michaels
Easton
Top hotels in Talbot County
St Michaels Inn
1228 S Talbot Street St. Michaels MD
Fully refundableReserve now, pay when you stay
S$125
13 Oct - 14 Oct
includes taxes & fees
8/10 Very good! (1,001 reviews)
"The location was the biggest plus for us with this stay - the hotel is right next to town and it's just a quick walk over to the grocery store. The staff was friendly and our room was ready on ti"
Reviewed on 22 Sept, 2026
The Tidewater Inn
101 E Dover St Easton MD
S$265
29 Sept - 30 Sept
includes taxes & fees
Inn at Perry Cabin
308 Watkins Ln St. Michaels MD
S$846
13 Oct - 14 Oct
includes taxes & fees
9.6/10 Exceptional! (403 reviews)
"Fantastic place; one of those that you don’t want to leave the property until the very sad time to go. Lovely staff, all of them, amazing food."
Reviewed on 20 Sept, 2026
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 Talbot County holiday package cost?
The most affordable Talbot County package is , so your dream trip can become a reality — without burning a hole in your pocket. Combine flights, hotels and car rentals to custom build a package that fits you.
How do I get a cheap travel package to Talbot County?
If you love bargains, bundle your bookings into a Talbot County holiday package. Whether you're searching for flights, hotels, day tours or rental cars, you can book everything in one place. You'll have endless choice at your fingertips too. Expedia has more than 550 airlines and 1,000,000 properties across the globe to choose from. Fly with who you prefer, stay in a place you like and save your hard-earned money — now that's the perfect getaway!
What are the top hotels in Talbot County?
For hotels in St. Michaels with friendly service and cosy beds, you can't beat Best Western Plus Easton Inn & Suites and Days Inn by Wyndham Easton. If you're visiting Easton as well, you'll get a solid night's sleep at Quality Inn or St Michaels Inn.
How far in advance should I book my Talbot County holiday?
Your best bet is to book early. Airlines generally advertise flight tickets nearly 12 months in advance, and this is when you can land some of the lowest prices. Just been told you should take all your holiday days in a few weeks? That's fine too — Expedia are never short on fantastic deals to send you on the getaway of your dreams, at a price you can afford.
What does an Expedia Talbot County travel package include?
It's up to you! You can choose from a variety of Talbot County bundles, such as a rental car, hotel and flight. You can also book a hotel with a flight, or a flight with a rental car. Once you've made your booking, you can add the fun stuff like activities and experiences. Whatever your ideal Talbot County escape looks like, you're sure to save!
What should I know before booking a Talbot County travel package?
So many places to travel to, so many things to experience. With a travel package, you'll be able to cross more of them off your list. Combine your flights, hotels and rental cars and land big savings.
Can I choose my airline with a Talbot County Expedia holiday package?
Yes, you can. Expedia has access to more than 550 airline partners across the globe, so fly with the carrier that suits your travel preferences.
If I'm not able to travel, can I cancel my Talbot County holiday package?
You can cancel your Talbot County booking if your plans have been upended. Whether you'll be charged a fee or not depends on your airline, hotel or car rental company. You may be able to cancel or change free of charge if you booked in the last 24 hours. Visit our Customer Service Portal to find out more.
Stay near popular Talbot County attractions
Photo by Louise Johnson
Chesapeake Bay Maritime Museum
9.4/10 (91 reviews)
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.
St. Michaels Marina
Explore the waterfront in St. Michaels with a trip to St. Michaels Marina.
Saint Michaels Village
You can browse for the perfect souvenirs at Saint Michaels Village during your stay in St. Michaels. Stroll along this romantic area's waterfront or simply enjoy its seafood restaurants.
St. Michaels Winery
8.6/10 (91 reviews)
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.
Avalon Theatre
9.0/10 (37 reviews)
You can get tickets for a performance at Avalon Theatre during your stay in Easton. Experience the festivals and museums in this family-friendly area.
Wye Landing
8.0/10 (1 review)
Explore the waterfront in Wye Mills with a trip to Wye Landing. Discover the seafood restaurants and its festivals while you're in the area.
Academy of the Arts
8.6/10 (13 reviews)
You can spend an afternoon browsing the exhibits at Academy of the Arts during your travels in Easton. Experience the festivals and museums in this family-friendly area.
Saint Michaels Town Hall
After visiting Saint Michaels Town Hall, make a plan to see the other sights and activities in St. Michaels.
What to do in Talbot County
St. Michaels: 2-Hour Relaxing Chesapeake Sail on Epiphany
S$343
per adult
St. Michaels: 2-Hour Wine Tasting on Sailing Cruise Epiphany
S$378
per adult
St Michaels: 2-Hour Chesapeake Bay Sail on Lady Patty
S$202
per adult
* 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.
