Kent Island Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Jennifer Crim

Top hotels in Kent Island

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 5.371.000 ₫ per night from 24 Aug to 25 Aug
5.371.000 ₫
6.628.338 ₫ total
24 Aug - 25 Aug
includes taxes & fees
9.4/10 Exceptional! (403 reviews)
"A gem of a hotel, rooms were nicely furnished and clean, staff are wonderful, nice grounds, good food. No complaints here!"

Reviewed on 20 Jul 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
8.8/10 Excellent! (1,824 reviews)
"Great place for a quick get away!"

Reviewed on 26 Jul 2025

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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 4.158.351 ₫ per night from 17 Aug to 18 Aug
4.158.351 ₫
4.740.520 ₫ total
17 Aug - 18 Aug
includes taxes & fees
9.4/10 Exceptional! (1,008 reviews)
"Beautiful place, very clean room, but the best thing by far was the staff. Everyone we met was friendly and helpful. Thank you so much for a greay stay!!"

Reviewed on 27 Jul 2025

Graduate by Hilton Annapolis
See all 1,345 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.

Popular places to visit

Paul Reed Smith Guitars

Enjoy an outing to Paul Reed Smith Guitars during your stay in Stevensville. You can enjoy the restaurants while in the area.

Paul Reed Smith Guitars

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 1null000null000 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.