Kent County Vacations & Trips from $482
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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 destinations in Kent County
Chestertown
Rock Hall
The Latest Kent County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Cozy Home near City Center with Hot tub
South Philadelphia
$2,507
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philadelphia (PHL)
10/10 Exceptional! (3 reviews)
This was the perfect place for my group and our needs. Enough beds with options; a dark, quiet room in the basement, a shared room with a two full beds, the top floor king size suite, even a pull out sofa! All useful accommodations for a party of 5 or more. To top it off, the roof top hot tub with a city skyline view was incredible! It was a great location too, in walking distance to our venue in South Philly. Everything worked out perfectly, and I'm grateful that this option was available. Thank you!
Reviewed on Mar 2, 2026
Find the Best Kent County Vacation Packages
Kent County Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Baltimore Washington Intl. Thurgood Marshall Airport (BWI) |
Top Sights | Eastern Neck National Wildlife Refuge, Ferry Park and Rock Hall Harbor |
Kent County Hotel Deals
Lord Baltimore Hotel
20 W Baltimore St Baltimore MD
$137 nightly
$161 total
Aug 13 - Aug 14
Total with taxes and fees
8.4/10 Very Good! (3,192 reviews)
"Good hotel with excellent location"
Reviewed on Aug 12, 2026
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
$98 nightly
$111 total
Aug 30 - Aug 31
Total with taxes and fees
8.8/10 Excellent! (1,087 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
$76 nightly
$87 total
Aug 23 - Aug 24
Total with taxes and 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.
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.
What to do in Kent County
Annapolis Harbor and U.S. Naval Academy Cruise
$34
per adult
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
