Top rated rentals — Kent County
Destination guide

Book a vacation rental for your Kent County getaway

Experience the unique character of Kent County with a stay in a vacation home rental. This city has something for everyone. Whether you're planning a family vacation, friends trip or romantic retreat, HomeAway has a great selection of vacation homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Things to do

Activities and attractions in Kent County

Are you searching for things to do while you're in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Kent County a fun place to get away. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • Queenstown Harbor Golf Club (16.1 mi / 25.9 km)
  • Bulle Rock Golf Course (23.3 mi / 37.5 km)
  • Dover International Speedway (28.7 mi / 46.3 km)
  • Tilmon's Island Winery (11 mi / 17.6 km)
  • Queenstown Harbor Golf Links (16.1 mi / 26 km)
  • Rocky Point Golf Course (18.8 mi / 30.3 km)
Natural features

Exploring the natural landscape of Kent County

Whether you're an outdoor enthusiast or just want to take in the scenery, Kent County is a great spot to appreciate mother nature. These are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • Rocky Point Park and Beach (18.3 mi / 29.5 km)
  • Gunpowder Falls State Park (18.4 mi / 29.6 km)
  • Elk Neck State Park (19.2 mi / 30.9 km)
  • Chesapeake Bay Environmental Center (20 mi / 32.2 km)
  • Sandy Point Beach (22.3 mi / 35.8 km)
  • Sandy Point State Park (22.4 mi / 36 km)

What are the top vacation rentals in Kent County?

Luxury villas, unique houseboats and spacious homes — everyone's ideal getaway is different. Whatever your tastes, you're sure to find something to tantalize you among these top vacation rentals in Kent County:

  • "Water Front Retreat - Sunrise And Sunset Water Views": If you're searching for somewhere in Chestertown with 3 bedrooms and plenty of charm, this getaway will tick your boxes. Amenities include a dishwasher and a dryer.
  • "Historic Downtown Chestertown Home. #1 Location": Stay a week or so at this property in Chestertown and make use of a barbecue grill, housekeeping services and more. It has 2 bedrooms to accommodate your friends and family.

For even more great options, use the search bar at the top of the page to find the perfect Kent County vacation rental for you.

What are the best tiny house vacation rentals in Kent County?

For a unique vacation experience, book a tiny house rental in Kent County. A word of warning though — after you've experienced life in a tiny house, the urge to move into one of thes cute-as-a-button digs will be tough to resist!

  • Enjoy a simpler way of living at "Annapolis Waterfront "tiny House" In Garden Setting". Amenities at this tiny house in Parole include a kitchen and air conditioning.
  • "A Serene Tiny Home Experience" offers conveniences such as a desk and shopping. Located in Parole, you'll be able to live large in this small but cleverly designed hideaway.

Can I find log cabins to rent in Kent County?

You'll find some awesome log cabins for rent in and around Kent County. Get the rustic cabin experience while staying in the heart of nature at either of these popular choices:

  • "Stunning Views From Waterfront Log Cabin With Fireplace On The Chesapeake Bay" has everything you need for a relaxing vacation, including nearby museums and beach sun loungers. Once you've settled in, get out and about and enjoy the lovely scenery.
  • You won't have to give up any home comforts at "1850 Historic Log Cabin". This sought-after escape features a smart TV, high-speed internet services and more.

What are the top-rated vacation rentals for weekend getaways in Kent County?

While long vacations are incredible, there's something undeniably lovely about embarking on a whirlwind weekend getaway. These rental properties in Kent County are perfect for just that:

  • "Country Estate In Historic District" - Found in Chestertown, this getaway offers handy extras including a TV and free WiFi.
  • "Circa 1900 Home In The Heart Of Historic Downtown Chestertown" - This is another fantastic place where you can unwind for a long weekend. Make the most of a kitchen, a TV and more during your short and sweet stay at this Chestertown property.

Can I find studio apartments for rent in Kent County?

Ditch the tired old hotel and secure one of our studio apartments in Kent County. Here's where you can hole up in your own pad and experience the next location you visit like a local:

  • Nap, eat, hang out with friends … Do it all from the compact yet cleverly designed single room space at "Eastern Shore Get Away". Located in Millington, heating and WiFi are on offer here.
  • Start your day with a cup of coffee and freshly cooked bacon and eggs at "First Floor Studio Apartment In Historic Chestertown". This Chestertown getaway has all the essentials to make your stay comfortable, including nearby ecotour services and off-street parking options.

Can I find short term rentals in Kent County?

Kent County has short-term rentals that come in all shapes, sizes and budgets. Take a quick break in an affordable cabin, a luxurious apartment or whatever else appeals to you. Below are two popular options to consider:

  • Set up camp close to central Chestertown and spend your days visiting the area's top sights from "Country Estate In Historic District". Along with its good location, this retreat has everything you need to make your vacation relaxed and hassle-free.
  • "Circa 1900 Home In The Heart Of Historic Downtown Chestertown" also rolls out the welcome mat for short-term guests. Spend a day or two at this property in Chestertown and see why it's a hit with many travelers.

What are the best romantic weekend getaways in Kent County?

Whether you've been paired up for a month, a decade or an eternity, there's nothing like a romantic weekend getaway to stoke the flames of love. If you're searching for the ideal place to spend a few days with your favorite person, check out these retreats:

  • Enjoy some "us time" at "Water Front Retreat - Sunrise And Sunset Water Views". This Chestertown property is perfect for romance, with amenities like beauty services and a fireplace to help set the mood.
  • Alternatively, organize an amorous weekend break at "Historic Downtown Chestertown Home. #1 Location". Located in Chestertown, it offers a nearby bay, beauty services and other highlights.

What are the best large group vacation rentals in Kent County?

If your idea of the perfect getaway is to bring the whole family, you're going to need a whole bunch of space. Luckily, there are plenty of vacation rentals in Kent County that are designed for large groups, starting with these sprawling retreats:

  • "Country Estate In Historic District": Featuring 5 bedrooms, this large vacation rental in Chestertown has enough room for you and all your friends. Amenities such as a garden and a firepit will keep everyone happy.
  • "Historic Stepne Manor On Maryland's Eastern Shore": Located in Chestertown, this sizable stay has 5 bedrooms and is another popular pick for a large family vacation. There's plenty to keep guests both entertained and comfortable, such as a kitchen and a garden.

What are the best houses for rent with a pool in Kent County?

You'll have your choice of houses with a pool in Kent County, so pull on your swimsuit and get set to spend your days chilling by the water. Here are some top-rated options that are sure to entice you:

  • The pool at "Rambling Victorian Beach House On Maryland's Eastern Shore" is guaranteed to add another layer of fun to your escape. Located in Betterton, this rental home also comes with childrens activities and on-site watersports.
  • "Carriage House Hideaway In Middle Of Chestertown" in Chestertown is another top pick. There's a lot to love about this place apart from its pool, such as towels and a TV.

What are the best large family vacation rentals in Kent County?

There's nothing like travel to bring your family together, but first, you need to find the perfect space. These family vacation rentals in Kent County come with tons of room to stretch out and relax with your loved ones:

  • "Water Front Retreat - Sunrise And Sunset Water Views" in Chestertown will make your family trip one you won't forget. It has 3 bedrooms sleeping up to 8 people and a range of amenities, including on-site watersports and outdoor furniture.
  • "Country Estate In Historic District" in Chestertown is another popular choice. You'll be able to invite up to 12 guests to this charming escape which has 5 bedrooms, a fridge, a toaster and more.