Kent Island Beach Vacations

Book a Beach Hotel + Flight or Car together to unlock savings

Photo by Jennifer Crim
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Find your perfect Kent Island beach vacation

How do I book the best Kent Island beach vacation packages?

Life’s a beach when you dive into our brilliant Kent Island beach vacation deals. Chuck a check in the filter boxes to find ocean views, pools, and resorts just a short saunter from the sizzling sands.

How can I find cheap beach vacations in Kent Island?

A rental steps from the shore creates an amazingly affordable Kent Island beach vacation. Seaside sojourns during low season start from . Prices and availability are subject to change. Additional terms may apply.

How can I book the best family beach vacations in Kent Island?

With a flick of a finger, the family-friendly filter brings you the best breaks on offer for the whole brood. Look out for kids’ clubs, waterparks, and other incredible extras for a vacay the little ones will love.

How do I find a Kent Island beachfront vacation?

Check the beachfront filter and, bam, the best available oceanside resorts will appear before your eyes. Along with the incredible view, when you book a beachfront resort, you can get from the lapping waves to your patio lounger in a matter of moments.

Can I book a package including a Kent Island vacation beach house rental?

Hit up the vacation rental filter to book your dream beach house. Once you’ve selected the most alluring abode, add your flights and car rental for the perfect package deal.

Can I find Kent Island beach vacation deals?

Sort your search results by deals to delight in amazing Kent Island beach vacation offers. If you want more pizzazz for your pennies, travel outside the high season or stay a little further from the shoreline.

Can I book a Kent Island beach trip with free cancellation and/or flexible dates?

Just like the Kent Island tides, plans change. Filter by payment option to find trips with free cancellation. Buy now, pay later options are also available for full-on flexibility.

Why should I book my Kent Island beach vacation with Expedia?

Relax long before you see the shore with simple search, fantastic filters, and more great deals than there are grains of sand in Kent Island. (OK, maybe not that last part.)

Top Beach Kent Island Hotels

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
  • 7 min drive from Matapeake State Park
Make the most of this fantastic location, as you'll be close to the beach with a holiday at this houseboat.
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

Floating 2 bed 2 bath condo stunning views of the bay
Chesapeake Houseboat Getaway on Kent Island, Maryland

Chesapeake Houseboat Getaway on Kent Island, Maryland

Stevensville
  • 7 min drive from Matapeake State Park
Make the most of this fantastic location, as you'll be close to the beach when booking a stay at this houseboat. Amenities at Chesapeake Houseboat Getaway on ...
9.8/10 Exceptional! (37 reviews)

Travelers like: close to beach, sun loungers, beach towels

Travelers say...
"I really enjoyed my stay. It's obvious Julia thought about all the little things when stocking the boat. Everything is very clean and modern. The sunroom was great to watch the marinas working boats come and go with fisherman and day sailers as well as observing the sea birds and ducks hanging out ..."

Reviewed on Aug 14, 2025

Chesapeake Houseboat Getaway on Kent Island, Maryland
Circa 1700 Chesapeake Colonial home on the National Register.

Circa 1700 Chesapeake Colonial home on the National Register.

Stevensville
  • 3 min walk from Matapeake State Park
Make the most of this fantastic location, as you'll be not far from the beach with a holiday at this vacation home. Available amenities at Circa 1700 Chesapeake ...
9.8/10 Exceptional! (53 reviews)

Travelers like: close to beach, outdoor pool

Travelers say...
"We adored our stay at Stevensville. Glen was welcoming and kind. We felt at home using the amazing pool and just enjoying the beautiful property. The house was comfortable and so much fun to see a piece of history so lovingly restored. The area was beautiful as well. We brought our three teens who ..."

Reviewed on Aug 14, 2025

Circa 1700 Chesapeake Colonial home on the National Register.
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.