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.

Where to stay around Kent Island?

Our 2019 property listings offer a large selection of 656 vacation rentals near Kent Island. From 433 Houses to 59 Cottages, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Kent Island for a holiday or a weekend are on HomeAway.

What are the most popular destinations to visit in Kent Island?

There are many lovely places to stay for a holiday trip or just for a weekend in Kent Island. From HomeAway travelers, the most popular destinations to visit are:

  • Baltimore: 290 vacation rentals
  • Annapolis: 506 vacation rentals
  • Saint Michaels: 157 vacation rentals
  • Chesapeake Bay: 6,009 vacation rentals
  • Chesapeake Beach: 510 vacation rentals

And HomeAway offers you the chance to discover many other popular destinations in Kent Island! Please use our search bar to access the selection of vacation rentals available in other popular destinations.

What are the main cities to discover in Kent Island?

Whether you're traveling with family or friends, here are the cities with the largest selection of vacation rentals for a holiday trip or just for a weekend in Kent Island:

  • Baltimore: 290 rentals
  • Annapolis: 506 rentals
  • Saint Michaels: 157 rentals
  • Chesapeake Beach: 510 rentals
  • Cambridge: 202 rentals

For other cities, please use our search bar to access the selection of vacation rentals available.

Near which points of interest can I spend my holidays in Kent Island?

HomeAway offers a large selection of rentals near lovely places in Kent Island. From HomeAway travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Breezy Point Beach: 201 rentals
  • Sandy Point State Park: 607 rentals
  • Baltimore Inner Harbor Marina: 176 rentals
  • Chesapeake Bay Bridge: 619 rentals
  • Harborplace: 334 rentals

But there are many other points of interest around Kent Island listed on HomeAway where you can find your place to stay. Just write your wanted destination in our search bar and have a look at our selection.