Kent Island Holidays

Book a Hotel + Flight or Car together to unlock savings

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    Save up to NZ$2,400 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Kent Island Holiday

Our pick of the best Kent Island Hotel Deals

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

180 Pier One Road Stevensville MD
Fully refundableReserve now, pay when you stay
NZ$415
19 Oct - 20 Oct
includes taxes & fees
9.4/10 Exceptional! (493 reviews)
"Exceptional experience, not a detail overlooked."

Reviewed on 18 Sept 2026

The Inn at Chesapeake Bay Beach Club
Kent Island Resort

Kent Island Resort

500 Kent Manor Dr Stevensville MD
NZ$332
12 Oct - 13 Oct
includes taxes & fees
Kent Island Resort
Island Life! Kent Island Waterfront with Pool-Bring your boat!

Island Life! Kent Island Waterfront with Pool-Bring your boat!

Stevensville MD
10/10 Exceptional! (217 reviews)
"The place was great"

Reviewed on 29 Aug 2026

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Island Life! Kent Island Waterfront with Pool-Bring your boat!
See all 1,323 properties in Kent Island
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.
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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.
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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.