Kent Island Vacation Packages

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Your Kent Island Vacation

Book a vacation package to Kent Island and travel on your own terms. You'll fall in love with its watersports, history and culture. Looking for ideas about where to stay on your trip to Kent Island? Chester is a top city you won't want to miss. Expedia has flights, hotels, car rentals and more to help you curate your own customized Kent Island vacation today.

Top Kent Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Hotel Laurel

DoubleTree by Hilton Hotel Laurel

4 out of 5
West Laurel
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Baltimore (BWI)
8.2/10 Very Good! (1,000 reviews)
This is definitely not four stars facility. More like two and half. Our stay for one night was ok. Sheets were clean. Fridge was missing in the cabinet in our room.

Reviewed on Aug. 14, 2025

The St. Gregory Hotel

The St. Gregory Hotel

4 out of 5
Downtown Washington D.C.
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Washington (WAS)
8.6/10 Excellent! (1,005 reviews)
Good location, friendly staff, great breakfast, clean and quiet rooms, best sleep in a week

Reviewed on Aug. 12, 2025

The Churchill Hotel near Embassy Row

The Churchill Hotel near Embassy Row

4 out of 5
Northwest
per person
Oct 31 - Nov 4
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Washington (DCA)
8.8/10 Excellent! (1,821 reviews)
I really enjoyed staying at a smaller hotel with charm! The staff is so nice and the location is great. Would stay here again.

Reviewed on Aug. 16, 2025

Club Quarters Hotel in Washington DC

Club Quarters Hotel in Washington DC

3 out of 5
Downtown Washington D.C.
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Washington (WAS)
8.8/10 Excellent! (1,624 reviews)
Dog friendly and plenty of dining options in walking distance! Also very quiet, I would come back

Reviewed on Aug. 14, 2025

Sagamore Pendry Baltimore

Sagamore Pendry Baltimore

5 out of 5
Fells Point
per person
Oct 3 - Oct 6
found 17 hours ago
Roundtrip flight included
Calgary (YYC) to Baltimore (BWI)
9.4/10 Exceptional! (1,009 reviews)
Staying at the Sagamore Pendry had been on my bucket list for years, and I finally made it happen for a special anniversary. The hotel is undeniably elegant, with exceptional staff and a clean, well-maintained atmosphere that reflects its historic charm. However, I couldn’t help but feel underwhelmed given the premium price point. There are several other hotels in the area offering comparable quality at a significantly lower cost. While the Pendry delivers a solid experience, it felt more like paying for a name than indulging in true luxury. I’m glad I checked it off my list, but I wouldn’t return—especially when value and experience don’t quite align.

Reviewed on Aug. 14, 2025

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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
Fully refundableReserve now, pay when you stay
The price is CA $311 per night from Aug 25 to Aug 26
CA $311
CA $380 total
Aug 25 - Aug 26
includes taxes & fees
9.4/10 Exceptional! (410 reviews)
"Beautiful setting on Maryland Eastern Shore."

Reviewed on Aug. 15, 2025

The Inn at Chesapeake Bay Beach Club
Floating 2 bed 2 bath condo stunning views of the bay

Floating 2 bed 2 bath condo stunning views of the bay

2 out of 5
Stevensville
8/10 Very Good! (4 reviews)
"Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby."

Reviewed on Jun. 7, 2025

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Floating 2 bed 2 bath condo stunning views of the bay
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Stevensville
9.8/10 Exceptional! (11 reviews)
"The property is excellent for entertaining and family gatherings. Everything was clean and tastefully appointed."

Reviewed on Aug. 14, 2025

Get rates
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
See all 1,351 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Kent Island

Chesapeake Exploration Center

Learn about the events happening at Chesapeake Exploration Center during your trip to Kent Narrows. Stroll along the area's marina or simply enjoy its seafood restaurants.

Chesapeake Exploration Center

Frequently asked questions

How much does a Kent Island vacation package cost?
Custom build your Kent Island vacation package from a low CA $624. 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.