$56 Car Rental Chester, CT

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Top Car Deals in Chester

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

Economy

Chevrolet Spark
  • 4 people
  • Unlimited mileage
New Haven, Connecticut, USA
Chevrolet Spark

$56

includes taxes & fees
$37 per day
found 10 hours ago
Economy Chevrolet Spark

Compact

Kia Soul
  • 5 people
  • Unlimited mileage
New Haven, Connecticut, USA
Kia Soul

$57

includes taxes & fees
$38 per day
found 10 hours ago
Compact Kia Soul

Midsize

Toyota Corolla
  • 5 people
  • Unlimited mileage
New Haven, Connecticut, USA
Toyota Corolla

$59

includes taxes & fees
$39 per day
found 10 hours ago
Midsize Toyota Corolla

Standard

Volkswagen Jetta
  • 5 people
  • Unlimited mileage
New Haven, Connecticut, USA
Volkswagen Jetta

$60

includes taxes & fees
$40 per day
found 10 hours ago
Standard Volkswagen Jetta

Fullsize

Toyota Camry
  • 5 people
  • Unlimited mileage
New Haven, Connecticut, USA
Toyota Camry

$60

includes taxes & fees
$40 per day
found 10 hours ago
Fullsize Toyota Camry

Premium

Toyota Crown
  • 5 people
  • Unlimited mileage
New Haven, Connecticut, USA
Toyota Crown

$134

includes taxes & fees
$101 per day
found 8 hours ago
Premium Toyota Crown

Mini Van

Dodge Grand Caravan
  • 4 people
  • Unlimited mileage
East Haven, Connecticut, USA
Dodge Grand Caravan

$135

includes taxes & fees
$135 per day
found 8 hours ago
Mini Van Dodge Grand Caravan

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Lowest prices found within the past 10 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, Connecticut, provides the freedom and flexibility to explore the area at your own pace. With a rental vehicle, you can conveniently manage your luggage and create flexible travel plans, allowing you to visit numerous attractions in and around Chester. For outdoor enthusiasts and those seeking scenic experiences, destinations like Hammonasset Beach State Park, located 10 miles away, and Goose Island, just 8 miles away, offer beautiful landscapes and outdoor activities. You can also unwind at Westbrook Town Beach, which is only 9 miles from Chester.

Additionally, a rental car makes it easy to explore nearby cities such as Old Saybrook and Madison, both located 9 miles from Chester, where you can enjoy more beach experiences and cultural sites like the Katharine Hepburn Cultural Arts Center. Families or couples looking for romantic getaways will appreciate the convenience and comfort of having a vehicle, making it simple to discover the picturesque surroundings. Overall, a rental car enhances your visit to Chester by providing the flexibility to make the most of your trip.

Where to stay around Chester

  • Westbrook: Located 8 miles from Chester, Westbrook offers a charming experience for those seeking outdoor activities and scenic views. Popular attractions include Hammonasset Beach State Park and Gillette Castle State Park, both ideal for adventure and nature lovers. Visitors can enjoy the local beaches, including Harvey's Beach, and explore nearby restaurants and wineries, making it a perfect spot for romantic getaways.
  • Old Saybrook: Situated 9 miles away from Chester, Old Saybrook is a delightful destination known for its outdoor scenery and romantic ambiance. The area boasts attractions like Harvey's Beach and the Katharine Hepburn Cultural Arts Center, catering to both beachgoers and culture enthusiasts. With options for wineries and breweries in the vicinity, it's an excellent choice for travelers looking to unwind and enjoy local flavors.
  • Madison: Also 9 miles from Chester, Madison is a picturesque town that appeals to adventure seekers and nature lovers alike. The stunning Hammonasset Beach State Park and Hammonasset Beach are key highlights for those seeking outdoor fun. The presence of recreational areas and golf courses enhances the experience, while local dining options, including restaurants and wineries, make it a well-rounded destination for all travelers.

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

  1. Use filters to find the right car: Refine your search by vehicle type and features. Whether you’re looking for an SUV for additional space, a convertible for summer enjoyment, or an economy car for budget-friendliness, utilize the filters on Expedia to discover the best option for your journey.
  2. Book in advance to help lower costs: Rental prices can vary based on demand, so it's advisable to secure your car well ahead of your trip. By booking in advance, you’re likely to find lower rates and better availability, particularly during peak seasons.
  3. Consider a smaller car for savings: Smaller vehicles are typically more affordable to rent and are 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—might not be accessible. This can also apply to renters over 70. Always verify age requirements prior to booking.
  5. Check fuel policies: Some rental agreements operate on a full-to-full fuel policy, meaning you must return the car with a full tank to avoid additional fees. This is generally the most favorable option. Others may provide full-to-empty or prepaid fueling alternatives, which are also acceptable. Just ensure you return the car empty in that scenario.
  6. Save on city and airport pickups: Picking up your rental car at airports often incurs a surcharge, but the added convenience may justify the cost.
  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 should any unforeseen issues arise during your trip. Adding car rental insurance is a straightforward process when booking with Expedia.
  9. Consider unlimited mileage: If you're planning on taking long road trips, seek out rentals that offer unlimited mileage to steer clear of extra 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 $56.

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
$56
Our second best deal of the day
$57
Our third best deal of the day
$59
From the airport to your hotel
Airport Transportation
From popular domestic and international airports
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Frequently asked questions

How much is a rental car per day in Chester?
The most affordable daily rate in Chester was $56 based on prices within the last seven days. Have a look at our impressive range of options, from small and affordable vehicles to classy, head-turning rides.
Can I rent a car from Tweed - New Haven Regional Airport (HVN)?
Touch down at Tweed - New Haven Regional Airport (HVN) and then head for Hertz or Budget, a short commute away. You'll be discovering the sights and sounds of Chester in your reliable rental before you know it.
What happens if I need to cancel my Chester car reservation?
There are always times when even the best-laid plans go wrong. That's why we provide your money back on many prepaid rentals if canceled at least six hours in advance of pickup. Don't forget to double-check your cancellation policy — sometimes it's not an option. Can't find the details there? Our Customer Service Portal is always here to help.
Where can I go on a road trip from Chester?
After you've checked out all of the well-known places in Chester, there's plenty more to explore in the region. Pick up the keys to a rental car, toss your luggage in the trunk and hit the open road. These are some drives we think you'll love:
  • Providence is 65 miles from Chester. Notable tourist attractions like Roger Williams Park Zoo should be high on your list here.
  • Your next pit stop? Albany, which is around 110 miles away. The Egg is one local highlight you won't want to miss.
  • Get out into nature and appreciate the serenity at Longwood Gardens. You'll find it around 200 miles from Chester.
How do I find the best car rental deals in Chester with Expedia?
Getting an amazing deal on your Chester rental car is a piece of cake with Expedia. Choose your preferred ride, add in a few more details and compare prices from leading brands. Why not add hotels and flights to your booking? You'll score even more savings when you combine your bookings into a package.
How old do you have to be to rent a car in Chester?
The minimum age to rent a vehicle in Chester is 21. A surcharge for young drivers applies, so check before booking and factor in any extra costs. There could also be restrictions on the categories of vehicles that can be rented by young drivers. For instance, some outlets will only rent out small and medium-sized cars to less-experienced motorists. Rules may vary between outlets, so read the fine print carefully.
What do you need to rent a car in Chester?
You'll need to present your driver's license and a credit card in your name at the rental counter. Prior to pickup, check with your rental provider whether other documentation is needed. For example, you may also need to show proof of insurance.
What is the cheapest car rental in Chester?
Chester has no doubt had some very happy car renters lately. The lowest daily rates recorded within the past seven days were $56 and $57. 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 Chester?
You can rent a car for a month or longer in Chester, so go on and extend your getaway! Just enter your trip details into our long-term car rental deals page and lock in your perfect ride.
Where can I find a Chester car rental if I am younger than 25?
Some Chester companies will rent cars to drivers under 25, and others won't. Age policies differ between suppliers, so you'll want to do your homework. Also, find out if there are extra costs. Some businesses will apply a surcharge to young customers between the ages of 21 and 24. Always look through the terms and conditions so you know what to expect.
What insurance should I choose for my car rental in Chester?
After meticulously planning your escape, don't scrimp on safety — add collision protection while booking your Chester car rental with Expedia. There are numerous benefits to this plan, including up to $35,000 in primary coverage for theft, vandalism and collision damage. Plus, with a zero-dollar deductible and 24/7 emergency help, you can breathe a little easier if the unexpected occurs.
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 also provides options like special vehicles starting from $16 a day. Compare suppliers on Expedia to find a 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 options starting from $30 a day and premium elite SUVs starting from $34 a day. These luxury rentals offer enhanced comfort and features for a more sophisticated travel experience. 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. This allows you to pick up your car in Chester and drop it off at a different location, which can be convenient for extended travel plans or if your itinerary ends in another city. For more options, explore Standard Car Rentals in Chester.
Can I rent a car round-trip in Chester?
Round-trip car rentals in Chester are a cost-effective option, starting from $12 a day. Picking up and dropping off your rental car at the same location in Chester generally helps avoid one-way drop-off fees, making it a great choice for exploring the city and its surrounding areas before returning to your original pickup point. 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 vehicles come with automatic transmission, offering ease of driving. Families often prefer SUVs or minivans for space, while couples and solo travelers find economy or compact cars suitable. Choose based on your passenger count, luggage needs, and travel 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 efficient for one person exploring at their own pace:
  • Economy 2 or 4 door, starting from $24 a day — fits up to 2 medium suitcases, nimble on city streets and simple to slot into small parking spaces
  • Compact 2 or 4 door, starting from $20 a day — fits up to 3 medium suitcases with a little more room for luggage while staying fuel-efficient
Both comfortably fit a solo traveler plus a bag or two. For extra comfort on longer drives, consider sizing up to a compact SUV, which starts from $21 a day. 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 3 large suitcases with smooth cruising for two
  • Compact SUV, starting from $21 a day — fits 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. These options provide a good balance of value and comfort for exploring Chester and its surroundings. 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 with room for 3 large suitcases and a car seat
  • Mini passenger van, starting from $29 a day — seats up to 8 with room for 6 large suitcases, ideal for larger families with strollers and full luggage
SUVs and minivans have ample 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 like December and September, 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 Enterprise provides electric options starting from $11 a day. Avis and Dollar Rent A Car also carry hybrid and electric cars, widely available on Expedia. Book EVs 4-6 weeks ahead as demand can be high, and plan charging stops for trips beyond 200 miles.
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, offering a wide range of vehicles. Sixt has midsize 2 or 4 door options starting from $15 a day and fullsize 2 or 4 door cars starting from $16 a day, which are easy to park and fuel-efficient. Enterprise offers midsize SUVs starting from $25 a day and economy 2 or 4 door cars starting from $26 a day, providing more space and comfort. Alamo rounds out the choices with midsize 2 or 4 door vehicles starting from $21 a day and economy 2 or 4 door cars starting from $24 a day. Other reputable providers include Avis and Dollar Rent A Car. Choose a car class that best suits your travel needs, whether it's a compact for city driving or an SUV for more space. For more options, explore Premium Car Rentals in Chester.
What are good day trip destinations from Chester by rental car?
Chester offers excellent opportunities for day trips by rental car, allowing you to explore nearby attractions and natural beauty. Consider these destinations for your next adventure:
  • Mystic Seaport in Mystic, Connecticut, is about 33 miles away, roughly a 40-minute drive. This historical and maritime destination is perfect for families and couples interested in cultural experiences.
  • The Goodspeed Opera House in East Haddam, Connecticut, is just 5 miles from Chester, a quick 10-minute drive. It is ideal for an evening out or a shorter cultural excursion for couples or adults.
  • Candlewood Lake in New Fairfield, Connecticut, is approximately 61 miles away, taking about 1 hour and 15 minutes to reach. This natural retreat offers scenic views and outdoor activities suitable for families or couples.
  • For an immersive nature experience, consider a Full-Day Private Hiking excursion in Kent Falls, Pond and Fuller Mountains, which is great for solo travelers or small groups seeking outdoor adventure.
To make the most of these day trips, selecting the right car rental is key. For families or groups with hiking gear, an SUV like a midsize SUV, starting from $17 a day, or a compact SUV, starting from $21 a day, provides ample space and comfort. Couples or solo travelers might prefer a more fuel-efficient option such as a midsize car, starting from $15 a day, or a compact car, starting from $20 a day, for easier navigation and parking. Always remember to fuel up before longer journeys and pack essentials like water and snacks, especially for outdoor adventures. 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 $56. 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.

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