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Kent County vacation rentals

We found 294 vacation rentals — enter your dates for availability

Discover a selection of 75 homes, 12 apartments, and other vacation rentals in Kent County that are perfect for your trip. Vacation homes offer the best amenities for your family, friends, or furry companion, such as parking and a hot tub. At the end of the day, you'll be sure to find a rental that has what everyone needs, including accessible or non-smoking choices.

Popular Kent County destinations on Vrbo

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Find out more about Kent County

Find out more about Kent County

Why visit Kent County

  1. Scenic Beauty: Enjoy picturesque views along the Chesapeake Bay, perfect for outdoor activities and relaxation.
  2. Historic Towns: Explore charming towns like Chestertown, featuring historic architecture and vibrant art scenes.
  3. Cultural Experiences: Immerse yourself in Kent County's rich history and diverse cultural offerings.
  4. Family-Friendly Activities: Discover a range of activities suitable for all ages, from parks to beaches.
  5. Cozy Accommodations: Choose from a variety of inviting vacation rentals, including homes, apartments, and cottages.

Popular types of accommodation in Kent County

Discover the perfect vacation rental in Kent County with options ranging from cozy cottages to spacious private homes and modern condos. Whether you're seeking affordable apartments or planning to rent in Parkville or Suitland, our platform offers a variety of choices to suit your needs. Enjoy transparency and savings while finding the ideal accommodation for your getaway. Let us help you make the most of your Kent County experience!

  • Apartments: The top choice for visitors in Kent County, offering convenient amenities and a home-like atmosphere.
  • Houses: A fantastic option for families or groups, providing spacious living areas and a personal touch.
  • Cottages: These quaint and charming retreats are perfect for a cozy getaway by the water.
  • Condos: A popular choice for those seeking modern living with shared amenities in a community setting.
  • Caravan Parks: Ideal for outdoor enthusiasts, offering a unique experience with access to nature and recreational activities.**

Top attractions in Kent County

Kent County, Maryland, is perfect for outdoor enthusiasts and those seeking romance, offering a blend of scenic beauty and cultural experiences. Visitors can explore historic colleges and universities, enjoy the charming harbors, and relax on the beaches. The area caters to families and cultural explorers alike, making it an ideal destination for a memorable vacation. Don't forget to request tours to fully experience what Kent County has to offer!

  1. Washington College: Established in 1782, this historic institution boasts beautiful architecture and a vibrant campus atmosphere. Explore its rich history, engaging cultural events, and art exhibitions that reflect the college's commitment to liberal arts education.
  2. Rock Hall Harbor: A picturesque harbor known for its stunning waterfront views and charming boating community. Enjoy leisurely walks along the shore, fresh seafood dining, and the tranquil beach vibes that make it a perfect spot for relaxation.
  3. Betterton Beach: A lovely, sandy beach with a welcoming atmosphere, ideal for sunbathing and swimming. The family-friendly environment, combined with beautiful sunsets, provides a perfect backdrop for a memorable day by the water.

Things to do recommended for couples

For a romantic getaway in Kent County, visit Crow Farm and Vineyard. Enjoy wine tastings amidst beautiful scenery, perfect for intimate moments. Savor the entertainment and charming atmosphere that enhances your couple's experience, making it a memorable part of your vacation.

Things to do recommended for groups

Experience a captivating performance at the Garfield Center for the Arts at the Prince Theater, where culture and entertainment blend seamlessly. Enjoy a night filled with romance and family-friendly vibes that will create lasting memories for your group in Kent County.

What do I need to keep in mind when booking a vacation in Kent County

If you're traveling with a group, family, pets, or planning an extended stay, be sure to use the appropriate filters to prioritize your needs. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Kent County with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Kent County with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, as well as access to suitable amenities like a private pool. Additionally, thinking about how close you are to family-friendly attractions can make a big difference in your trip.
  • Taking your pets with you to Kent County: For many families, a vacation wouldn't feel complete without their furry companions. If you can relate, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Kent County: If you’re in search of vacation rentals with special offers for stays of a month or more, you’ve come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Kent County

Kent County, Maryland, is a hidden gem perfect for outdoor enthusiasts and romantic getaways. Explore charming towns like Chestertown, where historic architecture meets vibrant art scenes. Enjoy family-friendly activities and picturesque scenery, from the serene shores of the Chesapeake Bay to lush green parks. With its welcoming atmosphere and budget-friendly options, Kent County is an ideal destination for those seeking a unique blend of history, culture, and natural beauty.

  • Chestertown: Nestled along the Chester River, Chestertown is a charming town rich in history and natural beauty. Travelers flock here for outdoor adventures and stunning scenery. The town features an inviting boardwalk where you can take a leisurely stroll, admire the waterfront views, and enjoy recreational activities. Notable attractions include Washington College, a historic institution that adds to the town's educational charm, and a nearby marina perfect for boating enthusiasts. Chestertown is also known for its vibrant arts scene and annual events that celebrate local culture.
  • Rock Hall: Rock Hall is a picturesque waterfront town renowned for its stunning beaches and outdoor experiences. The inviting atmosphere makes it a favorite destination for beach lovers and those seeking relaxation by the water. Visitors can enjoy various recreational activities, from kayaking to fishing, at the local marina. The town's harbor provides a beautiful backdrop for sunset views and is an ideal spot for picnics. Rock Hall also boasts a welcoming community with quaint shops and eateries that offer fresh seafood and regional cuisine.
  • Galena: Galena is a delightful small town that offers a perfect blend of outdoor activities and family-friendly attractions. Known for its scenic landscapes, visitors can explore local parks and enjoy the area's natural beauty. The town features a charming boardwalk that invites leisurely walks, while nearby national and state parks provide ample opportunities for hiking and exploration. Families will appreciate the recreational areas that cater to all ages, making Galena an ideal spot for a memorable vacation experience.

Booking with Vrbo is simple

Are you hoping to save on your upcoming journey? Being flexible with your travel dates can really make a difference, as prices often fluctuate. Additionally, you can enjoy substantial discounts by opting for a longer stay. To discover a Vrbo property that aligns with your budget, feel free to use our filters to narrow down options by price, location, and type of vacation rental.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and enjoy OneKeyCash™ on your total booking amount. Being the organizer truly has its perks! When you enroll in our travel rewards program, One Key, you'll gain access to exclusive discounts and earn OneKeyCash™ on qualified bookings. Sign up today and start enjoying your savings right away!

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides a convenient hub for planning your travel. You can start new trips, refine your existing plans, or keep track of your reservations all in one place. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To check out the Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

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, Vrbo 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.

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)
  • Queenstown Harbor Golf Links (16.1 mi / 26 km)
  • Bulle Rock Golf Course (23.3 mi / 37.5 km)
  • Bay Hills Golf Club (24.8 mi / 39.9 km)
  • U.S. Naval Academy Golf Club (25.9 mi / 41.7 km)
  • Back Creek Golf Club (26 mi / 41.8 km)

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:

  • Betterton Beach (11.2 mi / 18 km)
  • Eastern Neck National Wildlife Refuge (14.9 mi / 24 km)
  • Miami Beach (17.6 mi / 28.3 km)
  • Rocky Point Park and Beach (18.3 mi / 29.5 km)
  • Chesapeake Bay Environmental Center (20 mi / 32.2 km)
  • Downs Park Dog Beach (20.7 mi / 33.3 km)

Frequently asked questions

What is the best area to stay in Kent County when booking a vacation rental?
If you’re planning a Kent County getaway, Galena is one of the most desired places to stay. Whether you go for a cottage, villa or different type of property, you’ll always have the whole place to yourself.
What is the most popular type of vacation rental accommodation in Kent County?
Based on our data, cottages are the most desirable property type in Kent County. But as you might expect, everyone’s idea of an epic trip differs. Vrbo has vacation homes with every shape, size and budget in mind, and we’ll help you discover the perfect match.
How much does it cost to rent a vacation rental in Kent County?
A range of things can determine how much you’ll pay for a vacation rental in Kent County, including the length of stay, type of property and season. Still, all Vrbo homes have something in common — exceptional value. Simply add your travel dates to find your home away from home.
How much does it cost to rent a beach house in Kent County?
Prices for beach houses in Kent County differ depending on the size and style of the property and when you’re traveling. Simply enter your travel dates into Vrbo and how many guests to view your options and prices. From there you can use the filters to narrow your search by amenities, ratings, nearby activities and more.
Are there pet-friendly vacation rentals in Kent County?
Yes. You’ll have your pick of 31 stays that welcome pets in Kent County on Vrbo. Our cuddly best friends need to get away from it all too, so simply use our search function for pet-friendly vacation rentals to book a perfect pad where Fido can be near his favorite humans.
Are there large group vacation rentals in Kent County?
With 24 vacation rentals that can host 10 or more guests in Kent County, you won’t have to hold back on your invites. From vacations with the extended family to events like weddings and birthday parties, Vrbo will help you find a large group rental to suit the occasion.
What are the top attractions for families in Kent County?
Keep the kids occupied at these leading family-friendly attractions in Kent County:

  • Historical Society of Kent County Maryland
  • Eastern Neck National Wildlife Refuge
  • Rock Hall Harbor

Are there one-bedroom vacation rentals in Kent County?
Kent County has 5 one-bedroom rentals available. Usually located in prime areas because of their compact size, a one-bedroom vacation rental is great if you’re traveling with a friend or your partner. And with plenty of home comforts like WiFi and more privacy, you’ll be able to chill out while enjoying this fantastic destination.
Can I find two-bedroom vacation rentals in Kent County?
Choose from 21 two-bedroom vacation homes in Kent County. Give your little ones the second room or maybe fill it with a couple of your besties. There’s plenty of space for whoever’s fortunate enough to be joining your journey.
Are there vacation rentals with WiFi in Kent County?
Kent County has 49 vacation rentals with WiFi, so you can stay connected when you’re away. Simply check the “WiFi” box in our search filter for a list of properties with this feature. From streaming movie blockbusters to scrolling social media, these Vrbo homes will keep you online.
How can I find vacation rentals with air conditioning in Kent County?
Pick from 80 vacation homes with air conditioning in Kent County providing that cool, cool breeze and extra comfort level. Just enter your dates of travel and then use our filter tool to look for properties with air conditioning.
How old do you have to be to rent a vacation rental in Kent County?
The minimum age requirements can vary across properties on Vrbo, so double-check the rules of the vacation home in Kent County you want to book. But usually, it’s 16, 18 or 21.
How long can I rent a vacation rental in Kent County for?
The amount of time you can stay in a Kent County vacation rental for varies depending on the property. Simply tap in your travel dates to see options that offer long-term stays. They come with all the things you need to make your extended vacation more enjoyable like kitchens and backyards. Some Vrbo vacation rentals may also offer weekly or monthly discounts, so you can stay longer for less money.
Does Vrbo offer discounts for vacation homes in Kent County?
Whether you’ve got your sights set on one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you’re sure to find some fantastic bargains and discounts on Vrbo. From weekend trips to extended vacations, we’ve got the perfect space for your next Kent County escape.

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