Kent Island 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 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
Southwest
CA $2,785
per person
Sep 27 - Oct 4
found 21 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Baltimore (BWI)
9.4/10 Exceptional! (1,215 reviews)
Great stay. Great neighborhood and beautiful new hotel with unusually large rooms and bathrooms.
Reviewed on Aug 10, 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 $301
CA $369 total
Aug 31 - Sep 1
includes taxes & fees
Kent Island Resort
500 Kent Manor Dr Stevensville MD
CA $226
CA $298 total
Sep 7 - Sep 8
includes taxes & fees
9.2/10 Wonderful! (172 reviews)
"I loved the kayaks!!"
Reviewed on Aug 4, 2026
Floating 2 bed 2 bath condo stunning views of the bay
Stevensville MD
7.2/10 Good! (9 reviews)
"Hands down the BEST experience I’ve had with VRBO! Kate was prompt with her communication and the boat was absolutely as she described! We are very much looking forward to going back!"
Reviewed on May 21, 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.
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.
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.
Frequently asked questions
How much does a Kent Island vacation package cost?
Custom build your Kent Island vacation package from a low CA $642. 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.
