$119 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

Mitsubishi Mirage
  • 4 people
  • Unlimited mileage
Queensbury, New York, USA
Mitsubishi Mirage

$119

includes taxes & fees
$100 per day
found 3 days ago
Economy Mitsubishi Mirage

Compact

Nissan Versa
  • 5 people
  • Unlimited mileage
Queensbury, New York, USA
Nissan Versa

$120

includes taxes & fees
$101 per day
found 3 days ago
Compact Nissan Versa

Midsize

Toyota Corolla
  • 5 people
  • Unlimited mileage
Queensbury, New York, USA
Toyota Corolla

$123

includes taxes & fees
$103 per day
found 3 days ago
Midsize Toyota Corolla

Fullsize

Nissan Altima
  • 5 people
  • Unlimited mileage
Queensbury, New York, USA
Nissan Altima

$125

includes taxes & fees
$105 per day
found 3 days ago
Fullsize Nissan Altima

Mini Van

Chrysler Pacifica
  • 7 people
  • Unlimited mileage
Queensbury, New York, USA
Chrysler Pacifica

$132

includes taxes & fees
$111 per day
found 3 days ago
Mini Van Chrysler Pacifica

Premium Pickup Regular Cab

Ford F150
  • 5 people
  • Unlimited mileage
Queensbury, New York, USA
Ford F150

$149

includes taxes & fees
$125 per day
found 3 days ago
Premium Pickup Regular Cab Ford F150

Luxury

Audi A4 Genesis G70 BMW 3 series
  • 5 people
  • Unlimited mileage
Queensbury, New York, USA
Audi A4 Genesis G70 BMW 3 series

$149

includes taxes & fees
$125 per day
found 3 days ago
Luxury Audi A4 Genesis G70 BMW 3 series

Standard SUV

Chevrolet Equinox
  • 5 people
  • Unlimited mileage
Queensbury, New York, USA
Chevrolet Equinox

$149

includes taxes & fees
$125 per day
found 3 days ago
Standard SUV Chevrolet Equinox

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Lowest prices found within the past 3 days. Prices and availability subject to change. Additional terms may apply.

What you need to know for your Chestertown car rental

Reasons to book a car rental in and around Chestertown

Renting a car in and around Chestertown provides the freedom and flexibility to explore the area at your own pace. With a rental vehicle, you can easily visit local attractions such as Friends Lake, known for its scenic beauty and romantic ambiance, or Loon Lake Beach, perfect for a relaxing beach day. The convenience of having a car also allows for easy luggage management and flexible travel plans, making it ideal for families or groups traveling together.

Additionally, a short drive to nearby destinations like Brant Lake, just 3 miles away, offers access to more outdoor experiences, including the Sagamore Golf Club, located 8 miles from Chestertown. Pottersville, 5 miles away, features both Loon Lake Beach and Friends Lake, providing ample opportunities for outdoor adventures. Overall, renting a car ensures a comfortable and efficient way to experience the natural beauty and attractions in and around Chestertown.

Where to stay in and around Chestertown

  • Brant Lake: Located 3 miles from Chestertown, Brant Lake is a charming destination known for its outdoor activities and stunning scenery. Ideal for a romantic getaway, travelers can enjoy skiing at local ski fields and resorts. Key attractions include the picturesque Lake George and Friends Lake, both perfect for outdoor adventures and relaxation. Brant Lake also offers delightful dining options, including local restaurants and wineries to enhance your stay.
  • Bolton Landing: Situated 10 miles from Chestertown, Bolton Landing is celebrated for its scenic beauty and outdoor experiences. This area is perfect for golf enthusiasts, featuring the renowned Sagamore Golf Club. Visitors can also explore the serene Million Dollar Beach and Lake George, which provide wonderful opportunities for romantic outings and scenic enjoyment. The neighborhood boasts a variety of restaurants and wineries to satisfy your culinary cravings.
  • Chester Shores: Nestled around Chestertown, Chester Shores is a delightful neighborhood that emphasizes outdoor and romantic experiences. Ideal for nature lovers, it offers access to ski resorts and fields for winter sports. Local highlights include Loon Lake Beach and Friends Lake, both of which are great for scenic views and outdoor activities. Chester Shores is also home to several nearby wineries, making it a perfect spot for those looking to unwind and enjoy the local flavors.

10 tips to save on your car rental in and around Chestertown

  1. Use filters to find the right car: Refine your search by vehicle type and features. Whether you're looking for an SUV for extra space, a convertible for summer drives, or an economy car for budget-friendly travel, use the filters on Expedia to identify the best options for your trip.
  2. Book in advance to help lower costs: Rental prices can vary based on demand, so it’s advisable to reserve your car well ahead of your trip. By booking early, you’re more likely to secure lower rates and enjoy greater availability, particularly during peak travel seasons.
  3. Consider a smaller car for savings: Generally, smaller cars are more affordable to rent and easier to park in crowded areas. Mid-size rentals strike a good balance between cost, comfort, and fuel efficiency.
  4. Age guidelines: Drivers under 30 may encounter higher deposits or daily fees, and certain vehicle types—such as SUVs or premium models—may not be available. This can also apply to renters over 70 years old. Always verify the age requirements prior to booking.
  5. Check fuel policies: Some rentals operate on a full-to-full fuel policy, meaning you must return the car with a full tank to avoid additional charges. This is typically the best option. Others may offer full-to-empty or prepaid fueling options, which are also acceptable. Just be sure to return the car empty in that case.
  6. Save on city and airport pickups: Picking up your rental car at airports often incurs a surcharge, but this could be worthwhile for the added convenience.
  7. Know your payment options: Many car rental companies exclusively accept credit cards for payment.
  8. Understand your insurance coverage: Car rental insurance can help you avoid unexpected expenses and provides peace of mind in case something unforeseen occurs during your trip. Adding car rental insurance is simple when booking through Expedia.
  9. Consider unlimited mileage: If you’re planning on taking long road trips, look for rental options that offer unlimited mileage to steer clear of extra charges.
  10. Bring your driver's license and ID: A valid driver's license is required to rent a vehicle.

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 from $119.

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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One Key members save 10% or more on select hotels, cars, activities and vacation rentals. Not only that, earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands: Expedia, Hotels.com and VRBO. Learn more and join today.

Car classes available from Expedia in 2026

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

Car Rental Information

Popular car types
SUV, Full Size, Economy
Car suppliers available
Our best deal of the day
$119
Our second best deal of the day
$120
Our third best deal of the day
$123
From the airport to your hotel
Airport Transportation
From popular domestic and international airports
Airport Car Rentals

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 $119. 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 $119 per day. The second lowest daily price offered in Chestertown was $120. 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.

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