Kent Island Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Beacon Hotel & Corporate Quarters

Beacon Hotel & Corporate Quarters

3.5 out of 5
Downtown Washington D.C.
Price was CA $921, price is now CA $629 per person
CA $629
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
7.6/10 Good! (1,006 reviews)
The young lady at the front desk was absolutely delightful...the rooms were clean but very cold and the hot water wasnt so hot. Outside of that the place was close to everything, clean, and safe.

Reviewed on Apr 8, 2026

The Westin DC Downtown

The Westin DC Downtown

4 out of 5
Downtown Washington D.C.
Price was CA $1,314, price is now CA $823 per person
CA $823
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
8.8/10 Excellent! (1,005 reviews)
No one is friendly here. The front desk, cleaning staff, bell service, no one. Not a great place for customer service

Reviewed on Apr 8, 2026

InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
Southwest
Price was CA $1,294, price is now CA $845 per person
CA $845
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Washington (DCA)
9.4/10 Exceptional! (1,068 reviews)
The room was very spacious, clean comfortable. It’s in a prime location with easy access to major attractions.

Reviewed on Apr 9, 2026

Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Downtown Washington D.C.
Price was CA $2,196, price is now CA $1,468 per person
CA $1,468
per person
Jun 14 - Jun 21
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Washington (DCA)
8.6/10 Excellent! (1,008 reviews)
No seating on balcony.

Reviewed on Apr 5, 2026

Lyle Washington D.C.

Lyle Washington D.C.

4.5 out of 5
Northwest
Price was CA $1,050, price is now CA $739 per person
CA $739
per person
May 21 - May 25
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
9.4/10 Exceptional! (1,668 reviews)
The hotel has comfortable, clean rooms, and a friendly staff.

Reviewed on Apr 6, 2026

Ready to book your vacation to Kent Island?

 

Choose your dates

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 $257 per night from Apr 12 to Apr 13
CA $257
CA $321 total
Apr 12 - Apr 13
includes taxes & fees
9.4/10 Exceptional! (446 reviews)
Beautiful Boutique Hotel on the eastern shore right over the Bay bridge great restaurant Little market that’s amazing nice spa and very pretty and accommodating hotel would highly recommend it!

Reviewed on Apr 4, 2026

The Inn at Chesapeake Bay Beach Club
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 MD
10/10 Exceptional! (17 reviews)
It’s beautiful place inside and out!

Reviewed on Apr 8, 2026

Get rates
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Chesapeake Houseboat Getaway on Kent Island, Maryland

Chesapeake Houseboat Getaway on Kent Island, Maryland

Stevensville MD
10/10 Exceptional! (51 reviews)
The houseboat was an absolute dream. We loved everything about it and really enjoyed our two night stay. Julia has thought of everything to make your stay comfortable. It was immaculate, well stocked and all the decor was beautiful. We would love to come back.

Reviewed on Apr 2, 2026

Get rates
Chesapeake Houseboat Getaway on Kent Island, Maryland
See all 1,300 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

Can I cancel my flight booking to Kent Island due to COVID-19?
If you haven't booked yet, go over the terms and conditions of your preferred airline. If you've already reserved your flight to Kent Island, click through to our Customer Service Portal. It will help you determine which COVID-19 policies apply to your reservation and advise the next steps.
What's the best way to find cheap flights to Kent Island that have flexible change policies?
We know that travel arrangements can change from one minute to the next, so locking in a flexible fare with Expedia is always a wise idea. Tick the "No change fee" box directly below the "Flexible change policies" filter. Your affordable, flexible flight to Kent Island is only a few clicks away.
What are some of the general tips for travelers to Kent Island during the COVID-19 outbreak?
With new COVID-19 rules and measures in place, travel looks a bit different at present. These are some handy things to know before you pack your suitcase for Kent Island:
  • Before locking in your flight, see if any travel bans or restrictions apply — in both your destination and origin. Get up-to-date information by reviewing government and travel websites.
  • When you pass through airport screening, do not remove your face mask. You will be required to lower it briefly for identification purposes. Passengers who refuse to wear a mask may be denied entry or boarding.
  • Do not hand your boarding pass directly to a TSA officer. Rather, position the pass on the reader and then hold it up for the agent to visually inspect it.
  • One container of liquid hand sanitizer is now permitted in your carry-on baggage. It must not be larger than 12 oz (350 ml), and you'll need to take it out of your bag at the X-ray machine for screening.
  • To reduce handling during screening, put items such as your keys, wallet, phone and belt into your carry-on rather than into the bins.
  • Separate any food you have for screening. Food items often trigger the alarm. Putting them in a clear plastic bag and into a bin reduces the need for a TSA officer to handle and inspect your belongings.

Which airlines fly to Kent Island?
Reserve your fare with Southwest Airlines and start working on your Kent Island must-do list. This popular airline runs 5336 flights every month to Baltimore Washington Intl. Thurgood Marshall Airport (BWI), a central gateway.
How can I find cheap tickets to Kent Island?
To get your hands on a great deal to Kent Island, book well in advance. Also use Expedia's handy "flexible dates" link above your search results. This will display the cheapest prices for similar time frames. In the last seven days, was the best price for a flight to Kent Island.
How much is a flight to Kent Island?
If you were flying one way from (), you could've locked in a cheap fare for just in the last seven days. Round-trip flights to Kent Island ranged from only to over the same period.
What are the most popular airports to fly into in Kent Island?
A major gateway to Kent Island, roughly 7430 flights touch down at Baltimore Washington Intl. Thurgood Marshall Airport (BWI) every month. Keep an eye out for a rewarding deal, book your fare and get set to enjoy the best of this fantastic region.
When is the cheapest time to fly to Kent Island?
Jet off early on in the week to bag a bargain airfare to Kent Island. Tuesday is routinely the most affordable day to fly, with Monday running a close second. Saturday typically has the costliest ticket prices. This is because a lot of people like to kick off their break on a weekend.
How much is a plane ticket to Kent Island?
In the last seven days, airfares to Kent Island ranged between and . Prices depend on the departure time, seating class, airline and how early you make your booking.
Which airlines with flights to Kent Island employ COVID-19 cleanliness policies?
As passengers and cabin crew take to the skies again, most popular airlines have introduced physical distancing and other necessary actions to help combat COVID-19. Here are some of them:
  • Southwest Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Spirit Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.