Kent Island Vacations

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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

180 Pier One Road Stevensville MD
Fully refundableReserve now, pay when you stay
NT$6,908
NT$8,483 total
Aug 31 - Sep 1
includes taxes & fees
9.4/10 Exceptional! (478 reviews)
"Do not stay here unless you're a guest of a wedding on the property. They do not care about any "regular" guests - you'll be refused at the door of the restaurant/bars because their on-site weddings reserve them (even if the bar is empty). Their staff also doesn't care about hospitality - they all ..."

Reviewed on 2026/8/14

The Inn at Chesapeake Bay Beach Club
Kent Island Resort

Kent Island Resort

500 Kent Manor Dr Stevensville MD
NT$4,973
NT$6,605 total
Sep 10 - Sep 11
includes taxes & fees
Kent Island Resort
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
NT$3,126
NT$3,564 total
Aug 30 - Aug 31
includes taxes & fees
8.8/10 Excellent! (1,098 reviews)
"This is our favorite hotel to stay in while in the Annapolis area. The hotel is clean inside and out. Staff are so wonderful and genuinely care about your happiness. And a price point that trumps other hotels by far. We've stayed at another hotel that is right beside this one and were very disappointed, ..."

Reviewed on 2026/8/16

DoubleTree by Hilton Hotel Annapolis
See all 1,310 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.
See properties

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.

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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.