Kent Island Holidays
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Your Kent Island Holiday
Book a holiday 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 customised Kent Island holiday today.
Kent Island Holiday
Kent Island Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Baltimore Washington Intl. Thurgood Marshall Airport (BWI) |
Top Sights | Matapeake State Park, Love Point State Park and Matapeake State Park |
Our pick of the best Kent Island Hotel Deals
The Inn at Chesapeake Bay Beach Club
180 Pier One Road Stevensville MD
Fully refundableReserve now, pay when you stay
AU$368
28 Sept - 29 Sept
includes taxes & fees
9.4/10 Exceptional! (482 reviews)
"Everything was amazing. This has been the perfect place for a little staycation with my husband. Loved it all!"
Reviewed on 28 Aug 2026
Kent Island Resort
500 Kent Manor Dr Stevensville MD
AU$298
14 Sept - 15 Sept
includes taxes & fees
9.2/10 Wonderful! (181 reviews)
"A charming property and great location. The staff was pleasant and accommodating. We had dinner at the restaurant, which was fabulous."
Reviewed on 27 Aug 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 21 May 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)
Matapeake State Park features serene Chesapeake Bay views from its beach and trails. Enjoy panoramic Bay Bridge vistas while picnicking, or visit the separate dog-friendly beach area.
Paul Reed Smith Guitars
Witness master luthiers transform raw wood into world-class electric guitars at this renowned factory. The 90-minute guided tour reveals meticulous craftsmanship from wood selection to final assembly.
Frequently asked questions
How much does a Kent Island holiday package cost?
Custom build your Kent Island holiday package from a low . 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 holiday 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 holiday?
It can be difficult to know when is the ideal time to book your holiday 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 travelling 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 holiday plans, there's bound to be a package that matches your budget.
Can I choose my airline with a Kent Island Expedia holiday package?
With a holiday 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 holiday 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 holiday 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.
