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Chestertown vacation rentals

We found 62 vacation rentals — enter your dates for availability

Discover a selection of 26 homes and other vacation rentals in Chestertown that are perfect for your trip. Vacation homes provide the amenities you need and want for you and your friends, family, or even pets, including parking and a garden. At the end of the day, you'll be able to choose a rental for everyone's needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Chestertown

Showing deals for:Aug 22 - Aug 29
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Why people love visiting cozy Chestertown

Take a vacation to Chestertown and enjoy the area's festivals, history and art galleries. This city's sporting events, university setting and boating draw many visitors. Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.

Activities and attractions in Chestertown

Do you want to find top things to see and do while you're in the area? Venture out of your vacation home and experience everything that makes Chestertown a one-of-a-kind vacation spot. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Queenstown Harbor Golf Club (16.7 mi / 26.9 km)
  • Queenstown Harbor Golf Links (16.7 mi / 26.9 km)
  • Compass Pointe Golf Courses (23.8 mi / 38.2 km)
  • Bay Hills Golf Club (25 mi / 40.2 km)
  • Cassinelli Winery and Vineyards (7.1 mi / 11.3 km)
  • Crow Farm and Vineyard (10.2 mi / 16.4 km)

Exploring the natural landscape of Chestertown

Whether you're an adventurous traveler or just want to spend some time taking in the scenery, Chestertown is a great place to spend some time outside. Here are some of the area’s noteworthy sights, all within 30 miles (48.2 km) of the city center:

  • Betterton Beach (10.5 mi / 16.9 km)
  • Ferry Park (11.5 mi / 18.5 km)
  • Eastern Neck National Wildlife Refuge (15.4 mi / 24.8 km)
  • Miami Beach (17.2 mi / 27.7 km)
  • Rocky Point Park and Beach (18.1 mi / 29.2 km)
  • Belcamp Beach (19.2 mi / 30.9 km)

Transportation options to and around Chestertown

The nearest airport is in Baltimore, MD (MTN-Martin State), located 20.3 mi (32.7 km) from the city center. If you can't find a flight that's convenient for your trip, you could also fly into Easton, MD (ESN-Easton - Newnam), which is 28.2 mi (45.3 km) away.

Frequently asked questions

What is the best area to stay in Chestertown when booking a vacation rental?
If you’re planning a Chestertown trip, Tolchester Beach is one of the most popular locations to stay. Whether you select a chalet, cottage or another property type, you’ll always have the entire place to yourself.
How much does it cost to rent a vacation rental in Chestertown?
Length of stay, season and property type are some factors that can affect the price of a vacation home. Simply click on your travel dates to find your ideal fit. From homey country cottages to plush villas, all Vrbo vacation rentals provide unbeatable value.
How much does it cost to rent a beach house in Chestertown?
Prices for beach houses in Chestertown can vary depending on the size and style of the property and time of year you’re traveling. All you need to do is enter your travel dates into Vrbo and the number of guests to see your rental options and prices. From there you can use the filters to tailor your search by ratings, amenities, nearby activities and more.
Are there pet-friendly vacation rentals in Chestertown?
With five properties that welcome four-legged guests, your furry best friend can also come along on your Chestertown getaway. Use the filter tool to browse our pet-friendly vacation rentals and find the pawfect pad on Vrbo.
Can I rent a house with a pool in Chestertown?
Add another level of fun to your getaway by booking one of the two houses with a private pool in Chestertown. Use our search filter to find properties with pools on Vrbo, then spend leisurely days splashing and playing in a swimming pool that’s for your exclusive use.
Are there vacation rentals in Chestertown that welcome kids?
Bring the entire family together for a fun-packed adventure in Chestertown at one of our five family-friendly properties. A lot of these stays offer conveniences that are just perfect for trips with the little ones, like kitchens, extra bedrooms and swimming pools. Just click on the “Properties good for families” filter box and choose your favorite option.
What are the top attractions for families in Chestertown?
Keeping the kids occupied during your stay in Chestertown is child’s play with these cool family-friendly attractions:

  • Rolphs Wharf Marina
  • River Arts Chestertown
  • Historical Society of Kent County Maryland

Are there vacation rentals with WiFi in Chestertown?
Whether you want to stay in touch with world events, check emails or post a pic to social media, there are four vacation homes with WiFi in Chestertown. Check the “WiFi” box when searching on Vrbo and stay connected on your getaway.
How can I find vacation rentals with air conditioning in Chestertown?
Chestertown has five vacation rentals where you can relax in air-conditioned comfort. To find a stay on Vrbo offering this amenity, choose your travel dates and use the handy filters to select the “air conditioning” box.
How old do you have to be to rent a vacation rental in Chestertown?
Age restrictions can differ between properties on Vrbo, so double-check the rules of the vacation rental in Chestertown you’re considering. But normally, it’s 16, 18 or 21.
How long can I rent a vacation rental in Chestertown for?
The length of time you can book a vacation rental in Chestertown varies according to the property. Just enter your chosen travel dates to look at a list of options offering extended stays. With tons of amenities like washing machines and air conditioning, as well as some offering discounted weekly or monthly prices, you’re sure to discover a perfect place to call your home away from home in Chestertown.
Does Vrbo offer discounts for vacation homes in Chestertown?
Whether you’re after one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you’re sure to score some fantastic bargains and discounts on Vrbo. From short stays to extended vacations, we’ve got the ideal place for your next Chestertown escape.

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