Chestertown Car Rental

Search and Compare from Car Companies in Chestertown

Photo by Julie Miller

Compare car suppliers to unlock big savings, and package your flight, hotel, and car to save even more.

Members save 10% more on select hotels, cars, activities and holiday rentals. Sign up.Opens in a new window

Enjoy maximum flexibility with penalty-free cancellation on most car rentals.

Frequently asked questions

Can I rent a car from Glens Falls, NY (GFL-Floyd Bennett Memorial)?
You can rent a set of wheels from Hertz, which is a quick commute from Glens Falls, NY (GFL-Floyd Bennett Memorial).
What happens if I need to cancel my Chestertown car reservation?
You should be eligible for a full refund on your booking if you let us know at least six hours before the pickup time. Check your car rental agreement for all the details. Our Customer Service Portal may have what you need too.
What types of cars can I rent in Chestertown?
Affordability, ease of parking and great mileage are among the reasons compact vehicles are the number once choice in Chestertown. Their small size makes them perfect for getting around the city. They're a great fit for couples, solo travellers and families on a budget. Of course, how you cruise around is totally up to you! Go even smaller with an economy or mini, or give yourself more space with a full-size or an intermediate. Chasing a little luxury? You'll love our premium options.
Where can I go on a road trip from Chestertown?
Chestertown has plenty to keep you on the move, but don't restrict yourself to just one place. Pick up a set of wheels and head off to explore the surrounding region. Here are some great options we've come up with:

  • You'll discover The Egg and many other interesting sights in Albany. From Chestertown, it's approximately 113 kilometres away.
  • Your next pit stop? Make it Springfield, which is around 193 kilometres away. Naismith Memorial Basketball Hall of Fame is one local highlight you won't want to miss.
  • Plymouth Rock is about 322 kilometres from Chestertown and is one of the region's most gorgeous nature spots. Stretch your legs and enjoy the fresh air.

How do I find the best car rental deals in Chestertown with Expedia?
It's easy to track down an incredible deal with Expedia. Simply choose your wheels, select your dates and preferred pickup and drop-off points, and compare offers from leading rental suppliers. Make even bigger savings when you bundle your Chestertown car rental with flight or hotel bookings.
How old do you have to be to rent a car in Chestertown?
If you're 21 and over, you can rent a car in Chestertown. Bear in mind that rental companies will charge young drivers an additional fee, which helps cover the higher accident or damage risk involved. Also, young drivers usually aren't permitted to rent luxury cars or larger vehicles. Browse the fine print before booking so there are no surprises when you pick up the keys.
What do you need to rent a car in Chestertown?
The main things are a valid driver's licence and a credit card in the same name. Most car rental companies will offer you insurance, which is optional. But you may be asked to provide proof of other coverage if you prefer to opt out. Make sure you check with your rental agency to avoid any hassles.
Can I rent a car for a month or longer in Chestertown?
Head to our long-term car rental deals page, enter your trip information and then lock in your perfect ride. Whether you're staying in Chestertown or venturing far beyond, Expedia will help you find a long-term rental at a fabulous rate.
Where can I find a Chestertown car rental if I am younger than 25?
Some Chestertown outlets will rent cars to drivers under 25 years old, and others won't. Age policies differ between suppliers, so you'll want to do your homework. Also, find out if there are additional costs. Some places will apply a surcharge to customers between 21 and 24. Make sure you read through the terms and conditions to avoid any nasty surprises.