Kent Island Beach Vacations

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

Photo by Jennifer Crim

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.
7/10 Good! (6 reviews)
"Husband & I stayed during the Annapolis boat show to get a feel for what living on a yacht would be like for our year Great Loop adventure and to see what boat features would be important to us when buying. This stay suited us perfectly and Kate’s communication with us with very quick. A minor mechanical ..."

Reviewed on Oct 8, 2025

Floating 2 bed 2 bath condo stunning views of the bay
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

stevensville
  • 14 min drive from Matapeake State Park
Make the most of this fantastic location, as you'll be within walking distance of the beach when booking a stay at this vacation home. Beach towels and sun loungers ...
10/10 Exceptional! (182 reviews)

Travelers like: on the beach, sun loungers, beach towels, waterpark

Travelers say...
"We had a beautiful time during our 4 day stay. Everything we could possibly need was provided from sunscreen to bug spray. Plus"

Reviewed on Oct 6, 2025

240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

Stevensville
  • 11 min drive from Matapeake State Park
Stay at this vacation home in Stevensville. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Romancoke Wharf County Park and Matapeake ...
9.8/10 Exceptional! (42 reviews)
"The host was very responsive and accommodating. The house was as advertised, with amazing views of the bay. Highly recommend."

Reviewed on Sep 9, 2025

Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
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.