Kent Island Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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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
Fully refundableReserve now, pay when you stay
The price is S$346 per night from 1 Dec to 2 Dec
S$346
includes taxes & fees
1 Dec - 2 Dec
9.4/10 Exceptional! (367 reviews)
"Love this property and Knoxie's is the best"

Reviewed on 19 Nov,2024

The Inn at Chesapeake Bay Beach Club
Kent Island Resort
Kent Island Resort
3.5 out of 5
500 Kent Manor Dr, Stevensville, MD
Fully refundable
The price is S$299 per night from 1 Dec to 2 Dec
S$299
includes taxes & fees
1 Dec - 2 Dec
9/10 Wonderful! (89 reviews)
"Wonderful stay, charming inn."

Reviewed on 14 Nov,2024

Kent Island Resort
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 S$205 per night from 24 Nov to 25 Nov
S$205
includes taxes & fees
24 Nov - 25 Nov
8.8/10 Excellent! (1,690 reviews)
"Love the hotel and stay here when I’m in town. Very happy to see the key system replaced, the old system was terrible. The WiFi still a bit slow for business and the room has no updated USB-C charging, no wireless charging and no clock. The staff is exceptional and that matters most!"

Reviewed on 18 Nov,2024

Historic Inns of Annapolis
See all 1,280 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 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.