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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.

Activities

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.

Weather

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, US?

Our 2020 property listings offer a large selection of 478 vacation rentals around Kent Island. From 324 house rentals to 45 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

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 Vrbo travelers, the top most popular destinations to visit are:

  • Annapolis: 346 vacation rentals
  • Historic District: 72 vacation rentals
  • Cambridge: 191 vacation rentals
  • Chesapeake Bay: 5,595 vacation rentals
  • Rock Hall: 95 vacation rentals

And Vrbo 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:

  • Annapolis: 346 rentals
  • Cambridge: 191 rentals
  • Rock Hall: 95 rentals
  • Saint Michaels: 155 rentals
  • Baltimore: 222 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?

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

  • Chesapeake Bay Bridge: 449 rentals
  • Edgar Allan Poe's Gravesite and Memorial: 240 rentals
  • Baltimore Inner Harbor Marina: 71 rentals
  • Harborplace: 246 rentals
  • Breezy Point Beach: 184 rentals

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

Explore destinations around Kent Island

Annapolis
346 vacation rentals
Cambridge
191 vacation rentals
Rock Hall
95 vacation rentals
Saint Michaels
155 vacation rentals
Baltimore
222 vacation rentals
Easton
313 vacation rentals
Chestertown
72 vacation rentals
North Beach
46 vacation rentals
Edgewater
364 vacation rentals
Tilghman Island
214 vacation rentals
Linthicum Heights
178 vacation rentals
Wittman
125 vacation rentals
Chesapeake Beach
357 vacation rentals
Pasadena
413 vacation rentals
Bozman
131 vacation rentals
Arnold
246 vacation rentals
Severna Park
420 vacation rentals
Queenstown
134 vacation rentals
Oxford
188 vacation rentals
Glen Burnie
212 vacation rentals