$65 Car Rental Chester, CT

These Chester insights are based on real traveler data from Expedia, aggregated using AI to help you plan your trip. Updated: August 20, 2026.

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 $65.

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.

We all love being rewarded

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.

• Compact car rentals    
• Convertible car rentals    
• Economy car rentals    
• Fullsize car rentals    
• Luxury car rentals
• Midsize car rentals    
• Mini car rentals    
• Minivan rentals    
• Pickup car rentals    
• Premium car rentals
• Sportscar rentals    
• Standard car rentals    
• SUV rentals    
• Van rentals