Discover a selection of 500 vacation rentals in Kent Island that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $100 per night, and houses and cottages are popular options for a stay in Kent Island. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Kent Island
Destination guide

Beaches, boats, and bridges, Kent Island is the jewel of Chesapeake Bay

The largest island in Chesapeake Bay, Kent Island is perched on the eastern shores of the Potomac River. It's most famous as the home of the Kent Narrows waterway, a popular leisure destination for boating, fishing, and watersports enthusiasts. Get your Maryland adventure off on the right foot and book a Kent Island vacation rental right on the waterfront. As the oldest English settlement in Maryland, this small island is stacked with old-fashioned charm. Visit Kent Fort, cycle the Cross Island Trail, and dine out in the seafood restaurants and crab shacks on the waterfront.

Things to do

Take a (Chesa)peake at one of the longest bridges in the world

Nestled under the famous Chesapeake Bay Bridge, which at 79,200 feet is one of the longest bridges in the world, engineering fans can delve into its long history at the Chesapeake Bay Heritage and Visitor Center in nearby Chester. History buffs can head south of the island to Kent Fort, the oldest English settlement in Maryland. Built in 1631, it's now little more than a clutch of stone markers. For a more tangible look at Kent Island's history head to the James E. Kirwan Museum in nearby Chester, the former home of the Maryland state senator.


Mind the Gap - Kent Narrows are a boater's paradise

Kent Island is a real outdoorsy kinda place. From fishing and sailing to hiking and biking, there's something for everyone. Head to the Kent Narrows, a waterway that connects the Chester River to the Eastern Bay, and go fishing, take a boat trip, or dine out in the crab shacks which line the waterfront. Beach bunnies can head south of Bay Bridge to Matapeake Beach, a sandy sweep great for sunbathing and swimming. A Kent Island vacation rental also makes a great base for tackling the Cross Island Trail, a popular cycling and hiking route around the island.


Sunshine on a rainy bay - Chesapeake in fall

Maryland's Eastern Shore tends to have a humid, subtropical climate and benefits from long, sunny, yet humid summers, where temperatures can often reach 90 degrees and above. Winters are cold and damp with temperatures dropping down to 30 degrees and below. In the cooler months, fall and winter, the area does see its fair share of the wet stuff, so pack wisely. The busiest time to visit Kent Island is during the summer months, when the sun shines almost everyday, and Kent Island vacation rentals are at their most desirable.

Natural features

Kent Island is a turtle-y fantastic place for nature lovers

Under the mass expanse of the Chesapeake Bay Bridge, Kent Island is part of Maryland's Eastern Shores. For a small island, Kent Island has stacks of natural attractions. Terrapin Beach Park is a quiet beach retreat covering 276 acres. Banked by bush, it has a boardwalk trail through the wetlands and natural salt marshes, where you can spot native birds like osprey, herons and swans, as well as turtles and bullfrogs. It's the start of the Cross Island Trail, and it's also the best spot on the island for sunsets.

How many vacation rentals are available around Kent Island?

Our 2021 property listings offer a large selection of 525 vacation rentals around Kent Island. From 432 house rentals to 46 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.