Kent Island Vacations from $201

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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.

The Latest Kent Island vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Arboretum
Hamilton Hotel Washington DC
YOTEL Washington DC
Club Quarters Hotel in Washington DC
Omni Shoreham Hotel
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Discover the most popular places to visit in Kent Island

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
$228 nightly
The price is $253 total per night from Aug 24 to Aug 25
$253 total
Aug 24 - Aug 25
Total includes taxes and fees
9.4/10 Exceptional! (407 reviews)
"Great location and amenities"

Reviewed on Aug 10, 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

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! (10 reviews)
A wonderful place with great hosts
"Everything was exactly as described on the listing. It’s the perfect spot for a peaceful and relaxing getaway, all while being close to a charming town. The hosts were very pleasant and easy to communicate with. I highly recommend this place!"

Reviewed on Jul 14, 2025

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