
Kent Island Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NT$25,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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
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

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

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
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 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.
Explore a world of travel with Expedia
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- St John's College
- Visit Maryland
- Visit Naval Academy
- Captain Avery Museum
- Annapolis Landing Marina
- Prince George's Stadium
- Rose Haven Vacations
- Visit Stevensville
- U.s. Naval Academy
- Compass Pointe Golf Courses
- Annapolis Harbour Center
- Queenstown Premium Outlets
- Shadyside Park
- Mcdaniel Vacations
- Ellen O. Moyer Nature Park at Back Creek
- Severna Park Vacations
- Kunta Kinte–Alex Haley Memorial
- Visit Oyster Harbor
- Annapolis Vacations
- Westfield Annapolis Mall
- Hammond-Harwood House
- Visit Edgewater
- Chesapeake Beach Railway Museum
- Annapolis Sailing School
- Sandy Point State Park
- Maryland State House
- Visit Queenstown
- Visit Annapolis
- The Third Haven Friends Meeting House
- Renditions Golf Club
- William Paca House
- Marley Vacations
- Queenstown Harbor Golf Club
- Maryland Quiet Waters Park
- Visit Gibson Island
- Anne Arundel Medical Center
- Bay Bridge Market Place Shopping Center
- Maryland Vacations
- Car rental Chester
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- Avis Rental Cars in Stevensville
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- Car rentals in Budget Newport News Apo-900 Bland Blvd
- Firefly Rental Cars in Annapolis
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
