Book Chestertown car rentals from

A trusted Expedia brand

Book a car in 3 easy steps

Find great deals

Recent car searches in Chestertown, New York, United States of America from per day

Don't see what you're looking for?

See all car rentals in Chestertown
View all cars

What are the major attractions in Chestertown?

If your trip to Chestertown is all organized but your travel itinerary is looking a little empty, we can give you a few hints and tips.

It's a good idea to have a plan before you set foot in a new destination. Two other attractions to squeeze onto your to-do list are Loon Lake Beach and Pack Demonstration Forest.

What are the best road trip destinations near Chestertown?

We know you're curious about what else is near you. Venture a bit outside of Chestertown and you'll stumble on some iconic attractions. About 37 miles away in Saratoga Springs, Congress Park attracts big crowds all year round. Why not head there and see what all the fuss is about?

Where are the best beaches near Chestertown?

Nothing screams vacation like hopping in the car, putting on some tunes and driving to the seaside. Chestertown has some awesome beaches close by, so bring along a good book (and a kite if it's windy) and take a day trip to one of these fantastic options:

  • Loon Lake Beach (2 miles away).
  • Veterans Memorial Park Beach (10 miles away).
  • Rogers Memorial Park Beach (10 miles away).

Where are the best convention centers near Chestertown?

If you're in town to attend a work conference, you'll find The Sembrich located 10 miles away. When you get a break, head to a nearby café to grab some food — networking and socializing can be very tiring.

How can I get a cheap car rental in Chestertown?

Avoid paying an arm and a leg for a rental car by following our top tips:

  • Our handy filter tool will be your new best buddy. Compare the biggest bargains from all of the top companies quickly and easily;
  • Register for our Price Drop Alert service and stay up to date when prices become cheaper for your destination;
  • Search for both airport and non-airport pickup outlet locations to ensure you're getting the absolute best offer around;
  • If your pickup and drop-off dates are not yet confirmed, try scoring a better price by choosing different days of the week in your search;
  • No one enjoys being hit with a late fee. Avoid the hassle of having to pay for another full day by making sure your pickup and drop-off times are similar;
  • Sometimes car rental outlets offer discounts if you pay upfront, so keep an eye out for these kinds of deals;
  • Don't let the deal you've been looking for slip through your fingers. Book as soon as you can and drive away with your dream set of wheels.

What kind of rental car should I get for Chestertown?

No other mode of transportation can give you convenience and freedom like your own wheels. Whatever the reason for your escape to Chestertown, CarRentals.com has an impressive range of vehicles to take your pick of. Heading to the city with your beau? Turn up the romance by renting a compact car or a mini. A joy to drive and a cinch to park, you'll love sitting side by side in one of these cute rides. A van is a good choice for large families. There's enough space for everyone and you can go wherever you want, when you want. If you're traveling for business, a premium car will get you from the boardroom to your hotel in comfort and style.

Should I get a luxury rental car in Chestertown?

For some, owning a luxury vehicle is little more than a lofty dream. But renting your dream car is far more achievable than you might think! Imagine cruising into town in a swish convertible, even if it's only for a day or two. Or perhaps all you want is a dependable set of wheels to get you safely from point A to point B. Flashy or affordable? Either way, one thing's for sure — there's a rental car to suit you in Chestertown.