Kent Island Vacation Packages
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Your Kent Island Vacation
Book a vacation package to Kent Island and travel on your own terms. You'll fall in love with its watersports, history and culture. Looking for ideas about where to stay on your trip to Kent Island? Chester is a top city you won't want to miss. Expedia has flights, hotels, car rentals and more to help you curate your own customized Kent Island vacation today.
Top Kent Island Vacation Deals
Price found within the past 48 hours. Click for updated prices.
InterContinental Washington D.C. - The Wharf by IHG
The Wharf
CA $799
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
9.4/10 Exceptional! (1,223 reviews)
Teddy is the reason my family will be coming back—and why I’ll recommend the InterContinental at The Wharf to anyone visiting the area.
The hotel is lovely and convenient, the rooms spacious and clean, and the staff warm and helpful. But Teddy took hospitality to another level.
My kids came back from an epic concert STARVING at 11:30 on a Sunday night. I shuffled down to the lobby in my pajamas, hoping to find a bag of chips or something to keep the teenagers alive until morning.
I found Teddy and asked if he knew anywhere I could still get food. He said, “Pizza and pasta okay? Follow me. I’ll take you to where we go.”
And he did! He walked me down the block to a lively Italian place I never would have found on my own, went inside, and made sure they would take care of me. Then he disappeared back into the night like the angel he was. Within 15 minutes, I was back at the hotel with pizzas.
I’d never been to The Wharf and had no idea where I was or what might still be open. Teddy could have simply pointed me in a direction. Instead, he immediately took it upon himself to solve my problem and literally walked me to the solution.
That is hospitality. The beautiful hotel may have gotten us there the first time. Teddy is the reason we’ll come back.
Reviewed on Sep 24, 2026
Ready to book your vacation to Kent Island?
Kent Island Hotel Deals
The Inn at Chesapeake Bay Beach Club
180 Pier One Road Stevensville MD
Fully refundableReserve now, pay when you stay
CA $270
CA $336 total
Oct 19 - Oct 20
includes taxes & fees
9.4/10 Exceptional! (496 reviews)
"Good stay. I wish I could have used the spa. It was closed on tuesdays. I also wish they could have provided free breakfast for the price that they charge per room"
Reviewed on Sep 25, 2026
Kent Island Resort
500 Kent Manor Dr Stevensville MD
CA $194
CA $263 total
Oct 12 - Oct 13
includes taxes & fees
9.2/10 Wonderful! (187 reviews)
"Excellent time, loved the property and speaking with the staff who were always helpful and friendly. Our room was beautiful and just added to the experience."
Reviewed on Sep 22, 2026
Floating 2 bed 2 bath condo stunning views of the bay
Stevensville MD
7.4/10 Good! (10 reviews)
"Kate and her husband were amazing. They helped us every step of the way. Even met us there to help learn our way around the boat. Definitely going again"
Reviewed on Sep 2, 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.
Stay near popular Kent Island attractions
Matapeake State Park
7.6/10 (4 reviews)
You can take time to visit Matapeake State Park during your travels to Stevensville. You can enjoy the restaurants while in the area.
Paul Reed Smith Guitars
Enjoy an outing to Paul Reed Smith Guitars during your stay in Stevensville. You can enjoy the restaurants while in the area.
Chesapeake Exploration Center
Learn about the events happening at Chesapeake Exploration Center during your trip to Kent Narrows. Stroll along the area's marina or simply enjoy its seafood restaurants.
Frequently asked questions
How much does a Kent Island vacation package cost?
Custom build your Kent Island vacation package from a low CA $705. Pick from any combination of hotels, flights and rental cars to craft the getaway you've been dreaming of. Remember to add on one or two experiences!
How do I get a cheap travel package to Kent Island?
Bundling your hotel and flight with Expedia won't just save valuable time — it'll save you a pretty penny too. A Kent Island vacation package makes it a breeze to put together your dream adventure. With more than 550 airlines worldwide to pick from, finding flights that fit your busy schedule will be no sweat. Not only that, we've got over 1,000,000 hotel options globally to choose from. Talk about choice! Whatever your budget, Expedia puts more of the world within your reach.
How far in advance should I book my Kent Island vacation?
It can be difficult to know when is the ideal time to book your vacation to Kent Island. But typically the earlier you book, the more affordable the prices. In some cases, you can secure your flights and hotels up to a year before your departure date. If you're thinking of a last-minute getaway, no need to panic! There are terrific bargains popping up on Expedia every single day.
What does an Expedia Kent Island travel package include?
That depends on what you want. If you're traveling alone, you might decide to bundle hotels and flights. Taking the whole family to Kent Island? A travel package including flights, hotels and rental cars might be a better fit. Expedia gives you the freedom to tailor your travel package.
What should I know before booking a Kent Island travel package?
A package can be easier on the hip pocket than individually booking all you need for your trip. For example, bundle your hotels, flights and rental cars and save a pretty penny. No matter your vacation plans, there's bound to be a package that matches your budget.
Can I choose my airline with a Kent Island Expedia vacation package?
With a vacation package, you're in control. Whether you're looking to fly to Kent Island in coach or first class, simply select from the available airline options. Expedia has access to more than 550 airline partners throughout the world.
If I'm not able to travel, can I cancel my Kent Island vacation package?
It's hard to predict what tomorrow might bring, so it's good to know that you can change or cancel your Kent Island vacation package. If you made your booking in the last 24 hours, you may be eligible for a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal to find out more.
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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.
