Kent County Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Phoenix Park Hotel
Northwest
CA $1,000
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
9.4/10 Exceptional! (2,183 reviews)
We stayed five nights for a family DC trip. The check-in was smooth and easy. Staff were friendly and helpful when I needed to have Amazon deliver a knee brace for my son. The location, being a 2-minute walk to Union Station, was a HUGE plus for us as my son couldn't walk as much as we planned. The only downside, which was nothing the hotel could control, is that the area is loud (especially if you're not from a big city). The hotel provided ear plugs. Amenities we enjoyed included: nice shampoo & conditioner, free espresso machines, and free bag-check. We'd stay here again.
Reviewed on Aug 16, 2026
Cozy Home near City Center with Hot tub
South Philadelphia
CA $4,024
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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
InterContinental Washington D.C. - The Wharf by IHG
Southwest
CA $1,756
per person
Sep 24 - Sep 28
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
9.4/10 Exceptional! (1,215 reviews)
We had a wonderful stay at the InterContinental. The hotel is in a great location. We enjoyed being on the Wharf. The river view was wonderful, and there are many great restaurants within walking distance.
Reviewed on Aug 18, 2026
The Mayflower Hotel, Autograph Collection
Downtown Washington D.C.
CA $1,240
per person
Nov 2 - Nov 6
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
8.8/10 Excellent! (1,001 reviews)
The stay was fabulous. The property was beautiful and the location was perfect.
Reviewed on Aug 17, 2026
Kent County Hotel Deals
Lord Baltimore Hotel
20 W Baltimore St Baltimore MD
Fully refundableReserve now, pay when you stay
CA $136
CA $160 total
Aug 30 - Aug 31
includes taxes & fees
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
CA $135
CA $154 total
Aug 30 - Aug 31
includes taxes & fees
La Quinta Inn & Suites by Wyndham Baltimore BWI Airport
1734 W Nursery Rd Linthicum Heights MD
Fully refundableReserve now, pay when you stay
CA $105
CA $120 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 $1,000. 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.
Ferry Park
10.0/10 (1 review)
Explore the great outdoors at Ferry Park, a lovely green space in 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.
What to do in Kent County
Ashes and Apparitions of Annapolis Ghost Tour
CA $35
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
