$235 Car Rental Chester, VT

These Chester insights are based on real traveler data from Expedia, aggregated using AI to help you plan your trip. Updated: August 16, 2026.

Reasons to book a car rental in and around Chester

Renting a car in Chester, Vermont, offers travelers the freedom and flexibility to explore local attractions and natural beauty at their own pace. With a rental car, you can easily visit notable sites like Bonnie's Bundles Dolls, located right in Chester, or venture to Lowell Lake State Park, a stunning outdoor destination just 9 miles away. For families interested in culture, the Vermont Museum of Mining and Minerals is a short 6-mile drive from Chester.

A car rental is particularly appealing for those seeking ski and adventure experiences, as it allows for convenient travel to popular destinations like Ludlow, 11 miles away, where you can enjoy Lake Rescue and Buttermilk Falls. Springfield, located 6 miles from Chester, features attractions such as the Baltimore Covered Bridge and Springfield Art and Historical Society Museum. Additionally, Grafton, also 6 miles away, offers sights like the Grafton Historical Society. With easy luggage management and flexible travel plans, renting a car enhances your experience in and around Chester, making it suitable for families, adventure seekers, and culture enthusiasts alike.

Where to stay in and around Chester

• Chester Depot: This charming neighborhood is located near Chester and offers a variety of outdoor experiences, particularly for those interested in skiing and adventure sports. Key attractions include Jamaica State Park and Lowell Lake State Park, both ideal for outdoor exploration, scenery, and adventure. Chester Depot is perfect for travelers looking to immerse themselves in the natural beauty of the area while being close to Chester's amenities.
• Ludlow: Situated 11 miles from Chester, Ludlow is a vibrant city that attracts travelers for its skiing and adventure activities. With attractions like Lake Rescue for stunning beach scenery and Buttermilk Falls for a romantic outdoor experience, Ludlow is a great choice for those looking to enjoy both relaxation and adventure. The area also features local wineries and breweries, making it a delightful spot for foodies and drink enthusiasts.
• Cavendish: Located 10 miles from Chester, Cavendish is another excellent option for adventure seekers. This city boasts access to ski resorts and outdoor activities, with notable attractions like Mount Ascutney and Mt Ascutney State Park nearby. Cavendish offers a mix of scenic views and opportunities for outdoor fun, along with local options for sweet treats and beverages, making it a well-rounded destination for visitors.

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 key features. Whether you require an SUV for additional space, a convertible for summer drives, or an economy car for budget-friendliness, utilize the filters on Expedia to discover the ideal match for your journey.
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 are more likely to secure lower rates and have a wider selection, particularly during peak seasons.
3. Consider a smaller car for savings: Smaller vehicles typically come with lower rental rates and are easier to maneuver in crowded areas. Mid-size options 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 types of vehicles—such as SUVs or premium models—might not be available. This can also apply to renters over 70 years old. Always verify the age restrictions before making a reservation.
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 generally the most convenient option. Other policies may include full-to-empty or prepaid fueling options, which are also acceptable. Just be sure to 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 make it worthwhile.
7. Know your payment options: Most car rental companies primarily accept credit cards for payment.
8. Understand your insurance coverage: Car rental insurance can help you avoid unexpected costs and provides peace of mind in case of unforeseen events during your trip. It's simple to add car rental insurance when you book through Expedia.
9. Consider unlimited mileage: If you plan to take long road trips, seek out rentals that offer unlimited mileage to prevent extra fees.
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 $235.

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