Kent Island Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Jennifer Crim

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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
The Inn at Chesapeake Bay Beach Club
4 out of 5
180 Pier One Road, Stevensville, MD
The price is AU$391 per night from 9 July to 10 July
AU$391
9 July - 10 July
includes taxes & fees
9.4/10 Exceptional! (391 reviews)
"Great"

Reviewed on 21 May 2025

The Inn at Chesapeake Bay Beach Club
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Stevensville
10/10 Exceptional! (190 reviews)
So relaxing!!
"This was our first VRBO experience and it was wonderful. The rental provided more than our expectations. It was a beautiful site and extremely clean.The host was friendly, kind and easily reachable. We highly recommend this rental location and host and will check here first for future trips to this ..."

Reviewed on 15 Jun. 2025

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Island Life! Kent Island Waterfront with Pool-Bring your boat!
Circa 1700 Chesapeake Colonial home on the National Register.
Circa 1700 Chesapeake Colonial home on the National Register.
Stevensville
9.8/10 Exceptional! (52 reviews)
Great family hang out!
"We were in town for a family wedding at the Kent Resort so this location was great! We all loved exploring this fascinating house- especially our architect son! The grounds are lovely and we enjoyed using the canoe and also hanging out on the patio with our coffee and listening to the birds ..."

Reviewed on 11 May 2025

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Circa 1700 Chesapeake Colonial home on the National Register.
See all 1,343 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.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.