Discover a selection of 500 vacation rentals in Kent Island, US 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 kitchens. Prices start at $294 per night, and houses and condos are popular options for a stay in Kent Island. Either way, you'll find a rental for everyone's needs.
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, US?

Our 2020 property listings offer a large selection of 581 vacation rentals around Kent Island. From 377 house rentals to 73 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent a shore-front property in Kent Island?

There's something incredibly soothing about being next to the water. If that sounds like the vacation of your dreams, you're in for a treat! Vrbo has no less than 135 vacation rentals with waterfront views in this destination. On the hunt for something a little different? See if any of our other properties tick your boxes. Our options for this destination include:

  • 121 water-view vacation rentals.
  • 88 city-center vacation rentals.
  • 48 waterfront vacation rentals.

Can I rent a house in Kent Island?

Rather than staying in a cookie-cutter hotel room this vacation, you could go for a whole house. You'll feel like part of the neighborhood before you know it! There are 379 houses currently available on Vrbo. Prices start from $58 per night. Or perhaps you'd prefer one of the area's other lodging types, like:

  • Apartment: 46 vacation homes. Prices start from $77 per night.
  • Cottage: 45 vacation homes. Prices start from $139 per night.
  • Townhome: 36 vacation homes. Prices start from $69 per night.

Can I stay in Kent Island in a large group?

The recipe for a perfect getaway is hanging out with your friends and loved ones in an amazing new place. If you'll be visiting with a large group, Vrbo can help you. Why not have a peek at the 58 house vacation homes available here? They're the leading choice for big groups of visitors. If you're traveling in a big group, the properties for rent that can meet your needs include:

  • If yours is a squad of 6, we have 129 vacation homes just right for that size. Spend a night from just $94.
  • After a vacation property for 8 people? We have 126 that will be ideal. You can book one for as little as $99 a night.
  • Organizing a trip away with a group of 10? We have 85 vacation homes that will be ideal. Prices begin at just $45 per night.

You and all your mates will be more than satisfied when you plan your Kent Island getaway through us!

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