Kent County Vacation Packages
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Your Kent County Vacation
Make planning your next getaway a breeze with a Kent County vacation package. Whether it's the food scene, history or something else entirely that brings you to this destination, our packages will help you discover the best of it. During your trip to Kent County, you'll want to tick off a few of its top cities. What shouldn't you miss? Chestertown. Expedia has flights, hotels and all your other travel needs to help you create your own customized Kent County vacation today.
Top Kent County Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Kent County Hotel Deals
Lord Baltimore Hotel
20 W Baltimore St Baltimore MD
Fully refundableReserve now, pay when you stay
CA $162
CA $190 total
Aug 16 - Aug 17
includes taxes & fees
8.4/10 Very good! (3,186 reviews)
"Very interesting had a lot of fun learning about the hotel.Itself, architecture is just beautiful, still, there are some things that could be updated a little.But overall, it was a great stay."
Reviewed on Aug 12, 2026
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
CA $136
CA $155 total
Aug 30 - Aug 31
includes taxes & fees
8.8/10 Excellent! (1,098 reviews)
"The staff were all great from reception to housekeeping. Unfortunately, the hotel is nothing like a Doubletree (except for the cookies). It has been woefully neglected, obviously for a long time. Upon entering the lobby at check-in, the smell of mildew/dampness was pervasive. It was even worse in ..."
Reviewed on Aug 12, 2026
La Quinta Inn & Suites by Wyndham Baltimore BWI Airport
1734 W Nursery Rd Linthicum Heights MD
Fully refundableReserve now, pay when you stay
CA $104
CA $118 total
Aug 23 - Aug 24
includes taxes & fees
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 Kent County vacation package cost?
We make it simple to travel somewhere new, with Kent County packages starting from as little as CA $1,617. You'll have the flexibility to combine your favorite hotels, airlines and car rental. For the ultimate getaway, why not add a few activities and tours to your travel itinerary?
How do I get a cheap travel package to Kent County?
Creating your own Kent County vacation package with Expedia is one of the easiest ways to save. We offer more than 550 air carriers and 1,000,000 hotel options around the globe. With such a huge range to choose from, you'll have no worries putting together your ideal getaway.
What are the top hotels in Kent County?
Comfort Inn & Suites Chestertown and Red Roof Inn & Suites Chestertown know how to make their guests feel welcome in Rock Hall. If you also plan to explore Chestertown, check out Driftwood Inn and Mariners Motel. Both are very popular with travelers.
How far in advance should I book my Kent County vacation?
Smart travelers often book early. You can normally start comparing international fares on Expedia up to a year before your intended flight. If you've left booking to the last minute, don't worry. Bargain prices sometimes occur just weeks before departure.
What does an Expedia Kent County travel package include?
With Expedia, you can choose any combination of car rentals, hotels and flights to build your perfect Kent County travel package. Once you've made your booking, you can add on the fun stuff like day tours and activities. Don't forget — the more you bundle, the greater the savings!
What should I know before booking a Kent County travel package?
So many places to wander around, so many things to do. With a travel package, you'll be able to check more of them off your list. Combine your hotels, flights and rental cars and make big savings.
Can I choose my airline with a Kent County Expedia vacation package?
You can, and with more than 550 airlines to choose from across the globe, it's all about choice. Scroll through the available options and find out which airline fits your needs and budget.
If I'm not able to travel, can I cancel my Kent County vacation package?
Whether it's your flight or hotel, you can cancel or change it. Locked in your Kent County vacation package in the last 24 hours? You may be able to make changes at no cost. For bookings made more than 24 hours ago, you may incur a fee from your hotel, airline or car rental company. For more information, head to our Customer Service Portal. We'll help you each step of the way.
Stay near popular Kent County attractions
Washington College
8.6/10 (87 reviews)
Take a campus tour or just explore the area of Washington College, during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
Rock Hall Harbor
9.6/10 (12 reviews)
Explore the waterfront in Rock Hall with a trip to Rock Hall Harbor. While in this family-friendly area, you can savor the top-notch restaurants.
Chestertown Historic District
Find out about the history of Chestertown with a stop at Chestertown Historic District. Experience the area's festivals and art scene.
Eastern Neck National Wildlife Refuge
9.8/10 (6 reviews)
Explore the great outdoors at Eastern Neck National Wildlife Refuge, a lovely green space in Rock Hall. Experience the area's entertainment venues and theater scene.
The Mainstay
8.0/10 (2 reviews)
You can get tickets for a performance at The Mainstay on your trip to Rock Hall. While in this family-friendly area, you can savor the top-notch restaurants.
Garfield Center for the Arts at the Prince Theater
6.8/10 (5 reviews)
You can get tickets for a performance at Garfield Center for the Arts at the Prince Theater on your trip to Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
River Arts Chestertown
7.4/10 (6 reviews)
Explore the campus of River Arts Chestertown, during your travels in Chestertown. Take in the festivals in this family-friendly area.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
