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.
Holiday Inn Columbia East-Jessup by IHG

Holiday Inn Columbia East-Jessup by IHG

3 out of 5
Price was CA $1,002, price is now CA $839 per person
CA $839
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
8.6/10 Excellent! (1,000 reviews)
Great place to stay, I got some great rest

Reviewed on Jun 8, 2026

Rachael's Inner Harbor Boutique Inn

Rachael's Inner Harbor Boutique Inn

3 out of 5
Ridgely's Delight
Price was CA $1,569, price is now CA $1,173 per person
CA $1,173
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
10/10 Exceptional! (4 reviews)
Beautiful and spacious

Reviewed on May 21, 2026

Capitol Hill Hotel

Capitol Hill Hotel

4 out of 5
Capitol Hill
Price was CA $1,212, price is now CA $976 per person
CA $976
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
9/10 Wonderful! (1,345 reviews)
Over-all the feel was of a well-maintained small hotel, decorated in good taste. Breakfast was above average ; staff friendly and helpful. Hotel was close to the mall and many small restaurants within walking distance.

Reviewed on Jun 13, 2026

Lord Baltimore Hotel

Lord Baltimore Hotel

3.5 out of 5
Downtown Baltimore
Price was CA $1,226, price is now CA $997 per person
CA $997
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
8.4/10 Very Good! (2,765 reviews)
The bathrooms could be updated

Reviewed on Jun 14, 2026

Placemakr Buzzard Point

Placemakr Buzzard Point

4 out of 5
Southwest
Price was CA $1,244, price is now CA $1,045 per person
CA $1,045
per person
Jul 27 - Jul 30
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Baltimore (BWI)
9.2/10 Wonderful! (187 reviews)
A great unit for a great price. Interesting business model -- not your typical hotel and not for the technically challenged. It is located on the 6th floor of a large condo building. All contact is through your phone, so it is not easy to locate, get in, etc. You need a code for the garage (parking at $50/day is not included) which must be set up before arrival. You then need to figure out where to park for access to the right part of the building. Then you need to be buzzed in or use the app on your phone. App must also be used to operate the elevator. There is a small unit on the 6th floor which is used for check in where you can pick up a key fob for the doors and elevators. Unit itself was large, very modern and had everything we could need: large kitchen (a few wall plugs did not work), pod coffee maker, large living space, huge TV (streaming only, nothing local or live; initially remote did not work and needed batteries), separate bedroom and nice bathroom. Bed was super comfortable: the sheets, bedding and pillows were great. Shower was nice but water pressure in the bathroom sink was almost non-existent and despite letting the app and "front desk" know, it was not corrected while we were there. Unit was very quiet --there are quiet hours but I have no idea whom would enforce them if there was partying. The "pop-up" hotel was also located in a food dessert with no close by restaurants or stores.

Reviewed on Jun 3, 2026

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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 $316 per night from Jun 29 to Jun 30
CA $316
CA $386 total
Jun 29 - Jun 30
includes taxes & fees
9.4/10 Exceptional! (457 reviews)
"The hotel was clean and the staff were really nice. More of a resort than a hotel. I would recommend for the perfect getaway."

Reviewed on Jun 7, 2026

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 refundableReserve now, pay when you stay
The price is CA $202 per night from Jun 15 to Jun 16
CA $202
CA $271 total
Jun 15 - Jun 16
includes taxes & fees
9.4/10 Exceptional! (144 reviews)
"Amazing place! Great location! Cannot wait to return!"

Reviewed on Jun 14, 2026

Kent Island Resort
Floating 2 bed 2 bath condo stunning views of the bay

Floating 2 bed 2 bath condo stunning views of the bay

Stevensville MD
7.2/10 Good! (9 reviews)
"Hands down the BEST experience I’ve had with VRBO! Kate was prompt with her communication and the boat was absolutely as she described! We are very much looking forward to going back!"

Reviewed on May 21, 2026

Get rates
Floating 2 bed 2 bath condo stunning views of the bay
See all 1,309 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.
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Stay near popular Kent Island attractions

Matapeake State Park

3.8/5 (4 reviews)
You can take time to visit Matapeake State Park during your travels to Stevensville. You can enjoy the restaurants while in the area.
See properties

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.

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