$64 Car Rental Chester, MD

Reasons to book a car rental in and around Chester

Renting a car in Chester, Maryland, offers the freedom and flexibility to explore the beautiful surroundings at your own pace. With a rental vehicle, you can easily manage your luggage and create travel plans that suit your needs. This is particularly convenient for those looking to enjoy outdoor activities, scenic views, and beach experiences. Key attractions like the Chesapeake Bay Bridge, located 7 miles away, and Sandy Point State Park, also 7 miles from Chester, provide excellent options for adventure and exploration. Sandy Point Beach, just 6 miles away, is perfect for a relaxing day by the water.

Additionally, a rental car allows you to visit nearby destinations such as Annapolis, which is 11 miles from Chester and features historic sites like the Maryland State House, and Stevensville, only 1 mile away, known for its parks. Kent Island, located 3 miles from Chester, offers more opportunities to enjoy outdoor activities. Whether you are traveling with family or seeking a scenic getaway, renting a car in Chester enhances your travel experience by making it convenient to discover all that the area has to offer.

Top rated car suppliers in Chester

• Enterprise: With a rental location conveniently situated in Chester, Enterprise is a top choice for travelers seeking flexibility. The company is known for its excellent customer service and offers a diverse range of vehicles, especially Mini Vans and Standard cars. This makes it easy to manage your luggage and explore attractions around Chester at your own pace.

Where to stay around Chester

• Stevensville: Located only 1 mile from Chester, Stevensville is perfect for travelers seeking outdoor adventures and scenic views. Enjoy the beautiful beaches and explore the recreational areas nearby. Notable attractions include Matapeake State Park and Love Point State Park, both ideal for outdoor activities. The Chesapeake Bay Bridge, a modern landmark, is also easily accessible, making it a great spot for a family-friendly getaway.
• Grasonville: Situated 4 miles from Chester, Grasonville offers a charming atmosphere for families looking to enjoy beach experiences. The area features delightful boardwalks and shopping centres, perfect for leisurely strolls and shopping. Key points of interest include Sandy Point State Park, known for its stunning scenery, and Sandy Point Beach, which is ideal for beach vacations. Grasonville’s proximity to the bay enhances its appeal for outdoor enthusiasts.
• Annapolis: Just 11 miles from Chester, Annapolis is a vibrant city that combines family fun with a rich cultural experience. Visitors can enjoy a variety of activities, including shopping at local centres and exploring historical sites like the Maryland State House. Outdoor lovers can take advantage of nearby Sandy Point State Park and the Chesapeake Bay Bridge, making Annapolis a well-rounded destination for city-themed adventures.

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 desired features. Whether you need an SUV for extra space, a convertible for summer drives, or an economy car for budget-friendly travel, 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 wise to reserve your car well ahead of your trip. By booking in advance, you’re likely to secure lower rates and enjoy greater availability, particularly during peak 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 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 luxury 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 rentals operate on a full-to-full fuel policy, which requires you to return the car with a full tank to avoid additional charges. This is typically the most economical option. Others may offer full-to-empty or prepaid fueling alternatives, which can also be acceptable. Just ensure you return the car empty in such cases.
6. Save on city and airport pickups: Picking up your rental car at the airport often incurs a surcharge, but it may 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 provide peace of mind in case something unforeseen occurs during your trip. Adding car rental insurance when booking through Expedia is a straightforward process.
9. Consider unlimited mileage: If you're planning to embark on long road trips, seek rentals that offer unlimited mileage to sidestep additional 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 $64.

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.

• 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