Kent Island Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Jennifer Crim

  • Plan, book, travel with confidence

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    Better together

    Save up to ₩234,741 when you book a flight and hotel together*
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    Find the right fit

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

    Plan, book, and manage your trip all in one place

Find the Best Kent Island Vacation Packages

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 ₩283,919 per night from Aug 24 to Aug 25
₩283,919
₩350,384 total
Aug 24 - Aug 25
includes taxes & fees
9.4/10 Exceptional! (404 reviews)
"The location was excellent. The room was perfect. We had a complaint about noise from our neighbor and we were moved to another room with an apology from the staff for our experience. This service was superior!! We WILL be back!!"

Reviewed on Jul 28, 2025

The Inn at Chesapeake Bay Beach Club
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is ₩141,151 per night from Aug 12 to Aug 13
₩141,151
₩208,278 total
Aug 12 - Aug 13
includes taxes & fees
8.8/10 Excellent! (1,813 reviews)
"Enjoyed the stay! Beautiful place!"

Reviewed on Jul 28, 2025

Historic Inns of Annapolis
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is ₩214,643 per night from Aug 17 to Aug 18
₩214,643
₩244,693 total
Aug 17 - Aug 18
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
First class
"It was pouring when we arrived, my wife and i were soaked and the staff was at the front desk with warm towels. Beginning to end first class service, attentiveness and respectful."

Reviewed on Jul 28, 2025

Graduate by Hilton Annapolis
See all 1,346 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.

Frequently asked questions

How much does a Kent Island vacation package cost?
Custom build your Kent Island vacation 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 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.