Car Rental Chestertown, NY

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Top Car Deals in Chestertown

* Price found within the past 6 days. Click for updated prices.

Economy

Chevrolet Spark or similar
  • 4 people
Chestertown, New York, USA
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus or similar
  • 4 people
Chestertown, New York, USA
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla or similar
  • 5 people
Chestertown, New York, USA
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass or similar
  • 5 people
Chestertown, New York, USA
Jeep Compass
SUV Jeep Compass

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Frequently asked questions

How much is a rental car per day in Chestertown?
The daily price of car rentals in Chestertown within the past seven days was as low as . With your own affordable ride, the attractions in and around this place are easily within your reach.
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.
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 70 miles away.
  • Your next pit stop? Make it Springfield, which is around 120 miles away. Naismith Memorial Basketball Hall of Fame is one local highlight you won't want to miss.
  • Plymouth Rock is about 200 miles 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 license 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.
What is the cheapest car rental in Chestertown?
Based on prices within the past seven days, you could've slid into the driver's seat of a rental car for just per day. The second lowest daily price offered in Chestertown was . These rates were available on Expedia, with a rental starting date within the next year. Prices and availability are subject to change and additional terms apply.
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.
What insurance should I choose for my car rental in Chestertown?
A comprehensive insurance policy is a great choice for your upcoming Chestertown getaway. That's why we recommend purchasing collision protection while booking your car rental with Expedia. This covers your vehicle from theft, vandalism and accident damage. Some destinations may require a minimum level of liability insurance. It's possible that this is included in your rental price or your personal auto insurance, so check what you're covered for and if you need it.

Car Rental Information

 
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Finding the cheapest car rentals in Chestertown

Using our Search Wizard

If the deals that are available on our page do not suit your needs, then enter Chestertown into the search wizard at the top of the page. We will compare all the best deals available for your car rental in Chestertown and provide you with a list of the cheapest options, with no added fees.

Renting a car in Chestertown

Pay at pickup is available, so you don’t have to worry about spending your money until you arrive at your vehicle in Chestertown. We partner with reliable partners that guarantee an enjoyable experience for solo travelers, couples, and families. Package your car with a flight or hotel to unlock even more savings from Expedia.

Expected prices in Chestertown

Prices are subject to seasonal change depending on when you decide to arrange your car rental but right now you can book .

Flexibility & Cancellation

Most car suppliers offer penalty-free cancellations, so you don’t have to worry about losing money if your plans change. To cancel your booking log into your account through the Trips portal. Click manage booking and cancel this car. If you needed to alter your booking, then you can create a new one once you have canceled.

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Car classes available from Expedia in 2026

The classes of vehicles available will change depending on your chosen location.

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