$34 Car Rental Chester, NY

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Top Car Deals in Chester

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

Special

Dealers Choice
  • 4 people
  • Unlimited mileage
NEW YORK, USA
Dealers Choice

$34

includes taxes & fees
$22 per day
found 16 hours ago
Special Dealers Choice

Economy

Ford Fiesta
  • 5 people
  • Unlimited mileage
New York, New York, USA
Ford Fiesta

$34

includes taxes & fees
$22 per day
found 17 hours ago
Economy Ford Fiesta

Compact

Nissan Versa Note
  • 5 people
  • Unlimited mileage
NEW YORK, USA
Nissan Versa Note

$36

includes taxes & fees
$24 per day
found 17 hours ago
Compact Nissan Versa Note

Midsize

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

$37

includes taxes & fees
$24 per day
found 16 hours ago
Midsize Toyota Corolla

Standard

Volkswagen Jetta
  • 5 people
  • Unlimited mileage
NEW YORK, USA
Volkswagen Jetta

$38

includes taxes & fees
$25 per day
found 16 hours ago
Standard Volkswagen Jetta

Fullsize

Nissan Altima
  • 5 people
  • Unlimited mileage
NEW YORK, USA
Nissan Altima

$39

includes taxes & fees
$26 per day
found 17 hours ago
Fullsize Nissan Altima

Mini Van

Dodge Grand Caravan
  • 7 people
  • Unlimited mileage
NEW YORK, USA
Dodge Grand Caravan

$45

includes taxes & fees
$31 per day
found 17 hours ago
Mini Van Dodge Grand Caravan

Fullsize Elite Pickup Regular Cab

RAM 2500
  • 5 people
  • Unlimited mileage
JAMAICA, USA
RAM 2500

$72

includes taxes & fees
$50 per day
found 12 hours ago
Fullsize Elite Pickup Regular Cab RAM 2500

Standard Elite Special

Ford Mustang Mach-E
  • 5 people
  • Unlimited mileage
Jamaica, New York, USA
Ford Mustang Mach-E

$73

includes taxes & fees
$52 per day
found 17 hours ago
Standard Elite Special Ford Mustang Mach-E

Premium Pickup Regular Cab

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

$81

includes taxes & fees
$56 per day
found 12 hours ago
Premium Pickup Regular Cab Ford F150

Premium Elite SUV

Audi Q5 Genesis GV70 BMW X3
  • 5 people
  • Unlimited mileage
New York City, New York, USA
Audi Q5 Genesis GV70 BMW X3

$107

includes taxes & fees
$75 per day
found 17 hours ago
Premium Elite SUV Audi Q5 Genesis GV70 BMW X3

Oversize SUV

  • 0 people
  • Unlimited mileage
New York, New York, USA

$200

includes taxes & fees
$147 per day
found 17 hours ago
Oversize SUV undefined

Luxury

Audi A4 Genesis G70 BMW 3 series
  • 5 people
  • Unlimited mileage
JAMAICA, USA
Audi A4 Genesis G70 BMW 3 series

$280

includes taxes & fees
$200 per day
found 8 hours ago
Luxury Audi A4 Genesis G70 BMW 3 series

Luxury Elite SUV

Range Rover Sport BMW X7 Mercedes GLS
  • 5 people
  • Unlimited mileage
JAMAICA, USA
Range Rover Sport BMW X7 Mercedes GLS

$308

includes taxes & fees
$220 per day
found 8 hours ago
Luxury Elite SUV Range Rover Sport BMW X7 Mercedes GLS

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Lowest prices found within the past 16 hours. Prices and availability subject to change. Additional terms may apply.

What you need to know for your Chester car rental

Reasons to book a car rental in and around Chester

Renting a car in Chester, New York, provides you with the freedom and flexibility to explore the area at your own pace. With a rental car, you can easily navigate to key attractions such as Museum Village, which offers a rich cultural experience right in Chester. For outdoor enthusiasts, Bear Mountain State Park is only 15 miles away, perfect for scenic adventures. If you enjoy motorsports, the Orange County Fair Speedway, located just 9 miles from Chester, is an exciting destination. Additionally, a rental car allows you to visit nearby cities like Goshen, only 4 miles away, where you can explore the Harness Racing Museum and Hall of Fame, or Middletown, 10 miles away, featuring the Orange County Fairground. Families will appreciate the convenience of managing luggage and travel plans, while those seeking entertainment and adventure will find ample opportunities around Chester. Overall, renting a car enhances your travel experience by making it easy to visit multiple destinations and attractions in and around Chester, ensuring a memorable trip.

Where to stay around Chester

  • Chester: Nestled in a serene environment, Chester offers a quaint escape with its charming small-town feel. Visitors can enjoy local parks and outdoor activities that highlight the area's natural beauty. It serves as a great base for exploring nearby attractions.
  • Goshen: Located 4 miles away, Goshen is a vibrant city ideal for family and entertainment-themed experiences. Explore the Harness Racing Museum and Hall of Fame or enjoy events at the Orange County Fairgrounds. The town boasts various resorts and shopping options, making it a convenient choice for travelers.
  • Middletown: Situated 10 miles from Chester, Middletown is known for its dynamic atmosphere filled with entertainment options. Key attractions include the Orange County Fair Speedway and the Orange County Arboretum. With a range of restaurants and shopping centers, it's perfect for those seeking a city-themed experience.
  • Vernon: Located 16 miles away, Vernon offers a more adventurous experience, particularly for sports enthusiasts and skiers. Highlights include High Point State Park and Sussex County Fairgrounds, alongside opportunities for outdoor activities. It's an excellent choice for travelers looking to enjoy nature and adventure.

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

  1. Use filters to find the right car: Refine your search by selecting vehicle type and specific features. Whether you need an SUV for extra space, a convertible for summer fun, or an economy car for budget-friendly travel, utilize the filters on Expedia to identify the best option for your journey.
  2. Book in advance to help lower costs: Rental rates can vary based on demand, so it's advisable to reserve your car well ahead of your trip. By booking early, you are likely to secure lower prices and enjoy a wider selection, particularly during peak travel seasons.
  3. Consider a smaller car for savings: Smaller vehicles are typically more affordable to rent and easier to maneuver in crowded areas. Mid-size cars strike a great balance between cost, comfort, and fuel efficiency.
  4. Age guidelines: Drivers under the age of 30 may encounter higher deposits or daily fees, and certain vehicle types—such as SUVs or premium models—might not be available. This may also apply to renters over 70 years old. Always verify the age requirements prior to booking.
  5. Check fuel policies: Some rental agreements require a full-to-full fuel policy, meaning you must return the car with a full tank to avoid additional charges. This is usually the most favorable option. Others may offer full-to-empty or prepaid fueling terms, which are acceptable too; just be sure to return the car empty in those cases.
  6. Save on city and airport pickups: Picking up your rental car at airports often incurs an extra fee, but it may be worthwhile for the added convenience it provides.
  7. Know your payment options: Most car rental companies only 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 when booking through Expedia is simple.
  9. Consider unlimited mileage: If you’re planning long road trips, seek rentals that offer unlimited mileage to prevent additional charges.
  10. Bring your driver's license and ID: A valid driver's license is necessary to rent a car.

Finding the cheapest car rentals in Chester

Using our Search Wizard

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

Renting a car in Chester

Pay at pickup is available, so you don’t have to worry about spending your money until you arrive at your vehicle in Chester. 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 Chester

Prices are subject to seasonal change depending on when you decide to arrange your car rental but right now you can book from $34.

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.

Car Rental Information

Popular car types
SUV, Full Size, Economy
Car suppliers available
Our best deal of the day
$34
Our second best deal of the day
$36
Our third best deal of the day
$37
From the airport to your hotel
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Frequently asked questions

What are the best cheap car rental companies in Chester?
You can find cheap car rentals in Chester from $11 a day with Ace's economy 2/4 door cars. Sixt offers midsize 2 or 4 door cars starting from $15 a day, and fullsize 2 or 4 door cars starting from $16 a day. Dollar Rent A Car provides special vehicles starting from $16 a day. Compare suppliers on Expedia to find a cheap car rental in Chester that fits your budget. For more options, explore Economy Car Rentals in Chester.
What are the best luxury car companies in Chester?
For luxury car rentals in Chester, you can find premium options through providers on Expedia like Sixt and Enterprise. Sixt offers fullsize elite 2 or 4 door vehicles starting from $27 a day and fullsize elite SUVs starting from $30 a day. Enterprise also provides premium pickup regular cab vehicles starting from $30 a day and premium elite SUVs starting from $34 a day, offering more upscale choices for your trip. For more options, explore Luxury Car Rentals in Chester.
Can I rent a car one-way in Chester?
A one-way car rental in Chester is an excellent option for regional road trips, with prices starting from around $13 a day. Providers like Sixt and Enterprise may have flexible one-way policies, allowing you to pick up your vehicle in Chester and drop it off at a different location. These are good options for one-way car rental in Chester, offering convenience for travelers with varied itineraries. For more options, explore Standard Car Rentals in Chester.
Can I rent a car round-trip in Chester?
Chester is well suited to round-trip rentals, with round-trip rentals starting from $12 a day. Picking up and dropping off at the same location generally avoids one-way drop-off fees, which can make it the most cost-effective option for exploring the area and returning to the same spot. Providers like Sixt and Enterprise also offer wide round-trip availability, making it easy to plan your trip. For more options, explore Fullsize Car Rentals in Chester.
What are the best car rentals in Chester?
Car rentals in Chester offer extensive vehicle variety. The most popular car classes available include:
  • Midsize 2 or 4 door
  • Fullsize 2 or 4 door
  • Standard elite SUV
  • Midsize SUV
  • Standard 2 or 4 door
Most come with automatic transmission, and both automatic and manual transmissions are available. Families visiting attractions prefer SUVs or minivans for space; couples and solo travelers do fine with economy or compact cars. Choose based on passenger count, luggage needs, and budget. For more options, explore Minivan Car Rentals in Chester.
What are the best car rentals in Chester for solo travelers?
The best car rentals in Chester for solo travelers are economy and compact classes—small, easy to park, and cheap to run for one person exploring at their own pace:
  • Compact 2 or 4 door, starting from $20 a day — fits up to 5 people and up to 3 medium suitcases with a little more room for luggage while staying fuel-efficient
  • Economy 2 or 4 door, starting from $24 a day — fits up to 5 people and up to 2 medium suitcases, nimble on tight city streets and simple to slot into small parking spaces
Both comfortably fit a solo traveler plus a bag or two. If you're planning longer drives, consider sizing up to a compact SUV for extra highway comfort. For more options, explore Compact Car Rentals in Chester.
What are the best car rentals in Chester for couples?
The best car rentals in Chester for couples balance comfort and easy handling for two:
  • Midsize 2 or 4 door, starting from $15 a day — fits up to 5 people and up to 3 large suitcases with smooth cruising for two
  • Compact SUV, starting from $21 a day — fits up to 5 people and up to 3 medium suitcases with a higher ride for day trips around the region
Both give a couple comfortable seating and trunk space without being hard to park. For a special trip, consider a convertible for scenic drives around Chester. For more options, explore Midsize Car Rentals in Chester.
What are the best car rentals in Chester for families?
The best car rentals in Chester for families are the ones with room for everyone and their gear:
  • Midsize SUV, starting from $17 a day — seats up to 5 people with room for 3 large suitcases and a car seat
  • Mini passenger van, starting from $29 a day — seats up to 8 people with room for 6 large suitcases, ideal for larger families with strollers and full luggage
SUVs and minivans have room for the whole family plus car seats, strollers, and luggage, making them the most comfortable fit for trips around Chester. Book 4+ weeks ahead, as family-sized vehicles can have lower availability during busy periods, and consider adding GPS if you're new to the area. For more options, explore SUV Car Rentals in Chester.
Are there any car rental companies that provide electric cars in Chester?
Chester has excellent electric and hybrid vehicle options: Sixt offers hybrid vehicles starting from $11 a day and electric vehicles starting from $22 a day. Alamo Rent A Car also provides electric options starting from $11 a day. Multiple rental companies in Chester carry electric and hybrid cars, widely available on Expedia. EVs save on fuel, as charging costs less than equivalent gas cars. Book electric and hybrid vehicles 4-6 weeks ahead as demand can be high.
What is the best time to book a car in Chester?
From January, prices in Chester are typically lower—rentals can start from as little as $15 a day during this period. December and September tend to be the busiest months, when high demand can lead to higher prices. During major holidays and special events, rates may also fluctuate. Booking 3-4 weeks ahead can help with availability and pricing. Many bookings allow free cancellation 24+ hours before pickup—book early and rebook if rates drop.
What are the best car companies in Chester?
Car rentals in Chester are available from providers like Sixt, Enterprise, and Alamo Rent A Car, offering vehicles suited to local roads and conditions. Sixt has midsize 2 or 4 door cars starting from $15 a day and fullsize 2 or 4 door cars starting from $16 a day that are easy to park and fuel-efficient for city streets. Enterprise offers midsize SUVs starting from $25 a day and economy 2 or 4 door cars starting from $26 a day. Alamo Rent A Car rounds out the choices with midsize 2 or 4 door cars starting from $21 a day and economy 2 or 4 door cars starting from $24 a day. Choose a higher-clearance or all-wheel-drive class for varied terrain, and a compact class for easy maneuvering and better mileage on longer highway stretches. For more options, explore Premium Car Rentals in Chester.
What are good day trip destinations from Chester by rental car?
Chester offers convenient access to several excellent day trip destinations by rental car, perfect for families, couples, and small groups. You can explore:
  • LEGOLAND New York, just 3 miles away, is ideal for a fun-filled family outing. A compact or midsize car is perfect for this quick trip.
  • Woodbury Common Premium Outlets, located 10 miles from Chester, offers a wide selection of stores for retail therapy. A midsize or fullsize car provides ample space for your shopping bags.
  • Harriman State Park, about 16 miles away, is excellent for nature enthusiasts interested in hiking and outdoor activities. An SUV or standard elite SUV would be comfortable for this trip, especially if you are carrying gear.
  • The Catskill Mountains are approximately 55 miles from Chester, offering beautiful landscapes and outdoor adventures for a more extensive scenic drive. A fullsize SUV or midsize SUV would be well-suited for this longer journey, providing comfort and space.
When planning your day trips, remember to fuel up before you go and consider a car rental in Chester that offers enough space for passengers and any luggage or purchases you might make. For more options, explore Convertible Car Rentals in Chester.
Are there any hidden fees when renting a car on Expedia?
Expedia aims to show the key price and important rental details clearly during booking, so you know what to expect before you reserve. In some cases, car rental companies may apply additional charges at pick-up or during the rental, such as security deposits, tolls, fuel charges, extra driver fees, or local requirements, so it's worth checking the supplier's rental terms before you book.
Are there any long-term car rentals in Chester?
Yes, there are several long-term car rental options available in Chester. Whether you're planning an extended holiday with the family, relocating temporarily, or simply need a vehicle for several weeks or months, many car rental providers offer flexible long-term rental plans tailored to your needs. Click on our long-term car rental deals page, enter your trip information and then book a ride that suits.
Do you need insurance to rent a car in Chester?
No, you don't need personal auto insurance to rent a car in most cases. You will, however, be required to purchase some insurance to cover the duration of the rental. Rental companies will offer this insurance when you rent the car. Certain personal car insurance policies can also be applied to rental cars, and travelers can even use non-owner car insurance if they rent cars often but don't have a car of their own. Additionally, some car rentals simply include rental car insurance within the price of the rental.
How much does it cost to rent a car in Chester?
Budget car rental in Chester can be easy to find, with prices based on rates seen within the past seven days from $34. To find some of the cheapest options, sort your search results by price and use filters to match your budget and travel needs. For added flexibility, it's also worth exploring one-way car rentals.
What are the top car rental deals in Chester?
No matter what kind of vehicle you're looking for, Expedia makes it easy to find a great car rental deal in Chester. The easiest way to get a good deal on a rental car is to use our filters. At the top of the filter list, you'll find a section featuring our best car rental offers. Check the filter for "Great Deal," and your search results will be filled with specials. Compare offers from trusted rental providers, choose the option that fits your trip, and book with confidence. For even more value, bundle your Chester car rental with a hotel or flight to unlock additional savings.
What do I need to rent a car in Chester?
To rent a car in Chester, a current driver's license and a credit card in the same name are essential. If you're opting out of the company's insurance plan, then you may also need proof of other coverage. Rules may differ between rental companies, so read through your policy.
What happens if I need to cancel my Chester car rental?
If you need to cancel your Chester car rental, read over the policy to be sure, but almost all prepaid rentals are eligible for a complete refund if you notify us at least six hours prior to the pickup time, though there may be some exclusions so check your itinerary for more information, or just click through to our Customer Service Portal.
Why should I rent a car in Chester with Expedia?
Booking your car rental on Expedia makes it easier to get more out of your trip from the start. With a wide choice of car rentals, you can compare prices, suppliers and deals all in one place, then bundle your car with a hotel which could help you save even more. Join our free One Key™ travel rewards program to instantly unlock additional savings.

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