Enterprise Rent-A-Car

- 121 Flatland Rd, Chestertown, MD 21620

For residents across the Maryland Eastern Shore, and particularly in the Chestertown and Kent County area, convenient and reliable transportation is a necessity, not a luxury. Whether your personal vehicle is in the shop, you’re coordinating travel for a large group, or you’re planning a family trip to Annapolis or Ocean City, the local Enterprise Rent-A-Car branch on Flatland Road is your trusted neighborhood solution.

This location operates as a critical part of Enterprise’s extensive network, but maintains a distinctly local focus that sets it apart. The branch proudly identifies as a women-owned business, bringing a unique perspective to customer service and local community engagement. Their goal is to ensure a smooth, professional, and friendly rental experience, mirroring the feedback of happy customers who’ve highlighted the terrific assistance provided by individual staff members. This personalized touch is often difficult to find at larger, more impersonal airport locations.

As a local user in Maryland, you benefit from their commitment to flexibility and convenience. From the moment you call or book online, the team is geared toward getting you on the road with the right vehicle and the minimum hassle. They offer a full spectrum of vehicle types, from fuel-efficient economy cars perfect for navigating local Chestertown errands, to spacious minivans and full-size vans suited for transport across the Chesapeake Bay Bridge and beyond. Enterprise’s dedication to providing a seamless rental process is evident in their customer-centric policies, including their signature free customer pick-up service.

Customer reviews frequently praise the overall experience, noting the excellent service, the quality of the rental car provided, and the general efficiency of the process, including being picked up directly from a local garage—a testament to their neighborhood focus. While some callers noted occasional difficulty getting through on the phone, the service once engaged, is often highly rated for professionalism and effectiveness.

The Enterprise Rent-A-Car location is conveniently located in Chestertown, making it easily accessible for residents throughout Kent County and surrounding areas on the Eastern Shore of Maryland. Its position just off major local routes provides a straightforward journey for both pickup and return.

Address: 121 Flatland Rd, Chestertown, MD 21620, USA

As a non-airport branch, this location’s operating hours are typically focused on weekday business, with slightly limited hours or closure on weekends. Current hours generally run from 8:30 AM to 4:00 PM on Monday through Friday, and the branch is typically closed on Saturday and Sunday. Customers should always confirm the exact operating times for their specific rental dates to ensure a smooth process.

A significant highlight of this branch is its commitment to accessibility:

• Wheelchair accessible entrance: The facility ensures easy access to the rental office for all customers.
• Wheelchair accessible parking lot: Designated and compliant parking spaces are available to accommodate renters with mobility requirements, ensuring a convenient start and finish to the rental process.

This Chestertown branch is a fully equipped Car rental agency and Van rental agency, offering the following core services to the Maryland community:

• Extensive Fleet Options: Offers a comprehensive range of vehicles, including economy cars, compact cars, mid-size and full-size sedans, standard SUVs, and premium luxury models, catering to every travel need from personal errands to executive transport.
• Van Rental Agency Services: Provides specialized van rentals, including minivans for family road trips and large passenger vans (such as 12- and 15-passenger models) for group transportation needs on the Eastern Shore.
• Free Customer Pick-Up Service: Enterprise is famous for its ‘We’ll Pick You Up’ service, available during normal business hours at non-airport locations. This is especially helpful for customers needing transport from a local repair garage or home to the rental office.
• Active Military Discounts: Proudly offers special discounted rates and benefits to active-duty military members, veterans, and government personnel for both official and leisure travel.
• Flexible Payment Options: Accepts major Credit cards and Debit cards, providing flexibility. Importantly, the location also accepts NFC mobile payments (such as Apple Pay or Google Pay) for modern, fast transactions at the counter.
• Cross-Border Travel: Vehicles rented in the U.S. generally permit travel throughout the U.S. and Canada, offering flexibility for extended Maryland-to-North-East road trips.

Several distinct features make the Chestertown Enterprise branch an excellent choice for Maryland locals:

• Locally Owned and Operated: The business is identified as women-owned, which supports local business diversity and often contributes to a highly engaged and community-focused service model.
• Military and Government Focus: The availability of Active military discounts underscores a commitment to serving the region's military community, providing a valuable saving for both official and leisure rentals.
• Convenience of Free Pickup: The popular complimentary customer pick-up service eliminates the logistical headache of getting to the rental office, a major convenience feature for customers whose car is unavailable.
• Modern Payment Technology: Accepting NFC mobile payments shows the branch is equipped with current technology for quick, secure, and contactless transactions.
• High Service Scores: Customer testimonials consistently praise the smooth process, the quality of the rental vehicles, and the dedicated efforts of the staff, indicating a strong focus on high-quality service delivery.
• Robust Fleet Variety: As both a Car rental agency and a dedicated Van rental agency, they can meet virtually any local transportation need, from a solo traveler to a large church or university group.

For current operating hours, to arrange the free pick-up service, or to make inquiries about your reservation at the Chestertown, MD location, please use the contact information below.

Address: 121 Flatland Rd, Chestertown, MD 21620, USA

Phone: (410) 810-0971

Mobile Phone: +1 410-810-0971

Choosing Enterprise Rent-A-Car on Flatland Road is a smart choice for any Maryland local, particularly those on the Eastern Shore, due to its unparalleled combination of community focus and convenient services. The fact that this is a women-owned business immediately sets a positive, distinct tone, which often translates into highly attentive customer service, as reflected in the stellar reviews mentioning staff going above and beyond.

For a community where access to transport can sometimes be challenging, the free customer pick-up service is a standout, invaluable feature that truly sets Enterprise apart from its competition. It’s a genuine commitment to convenience that greatly reduces the stress of rental when you are without your own vehicle. Add to this the benefit of active military discounts, which provides a tangible advantage to a deserving segment of the Maryland population, and you have a rental agency that is deeply tuned into local needs. The acceptance of varied payment options, including NFC mobile payments, is a modern convenience that makes the transaction process fast and easy. In summary, whether you need a reliable car for a month (as one customer did, putting 3200 miles on it without issue) or a van for a short trip, the Chestertown Enterprise branch offers a blend of quality fleet, flexible policies, and high-touch local service that makes it the premier option in the area.

Enterprise Rent-A-Car

121 Flatland Rd, Chestertown, MD 21620, USA