Need a rental car in Chesapeake, VA? Enterprise Rent-A-Car is Here For It. Whether your car is in the shop, you're running errands, or planning a weekend getaway, we're ready with a wide range of vehicles and flexible rental options. Enjoy easy, stress-free rentals and friendly service that gets you on your way fast. Reserve your rental car with Enterprise at our Greenbrier & Military location today.
They will cancel your reservation if they do not Spk with you when they call to confirm. And they do not use all contact methods before cancellation. We made this reservation 3 months in advance. They ended up inconveniencing us by placing us in two mini vans and requiring a deposit for both vehicles when it was there error. So not only had to get another driver we had to both drive 5 hour to and from, gas two vehicles and had to omit a person from our family reunion trip bcuz the vans seated only 7 per van not what we originally requested 15 passenger van. And Manager never called us back before the trip as requested. If we hadn’t of called to check 3 days prior to reservation we would’ve been without anything. I recommend this company to my family for our family reunion. I will never use them for a group gathering again. And the vans were half full but when we returned them they both were returned full. They didn’t try to correct the situation to our satisfaction. They just use the price of the 15 passenger towards splitting two vans but wouldn’t waive one deposit for the van. Unprofessional! Do Better Enterprise. 😞🙁
AJ
Avery Jones
Jul 20, 2026
5.0
Over the Top 5 Star Service, the boss lady was of the highest level of customer service, period. (I may have her name incorrect, Iyana) was most helpful in her commitment to keep my reservation, in critical times (because I saw the entire area/three of the seven cities) deprived of supply for car rentals. This lovely young lady did everything in her power to locate a proper vehicle according to my specifics, she adjusted my reservation a couple times to accommodate the inconvenience of rental shortages and availability, ultimately landing everything absolutely 100 percent perfect. I could not be by much, more pleased with the entire process of services. The transaction was smooth, considerate in every way, and I can hardly wait to have the opportunity to request this locations services again. As far as any Enterprise services I've ever encountered, this was by far, the best in setting the bar. I was very please and everything was flawlessly simple. For that I Thank this young boss lady. Enterprise you caught a gem with this one. Undoubtedly!!
RR
Raquel
Jul 14, 2026
5.0
⭐⭐⭐⭐⭐
After an incredibly frustrating experience with multiple Enterprise locations and an insurance claim, Marcus at the Enterprise location on Military Highway completely restored our faith in customer service.
My husband's car was at a repair shop to have a front rim repaired when one of the shop's employees accidentally hit his vehicle with another car, causing additional damage, including the rear rim. The shop owner filed an insurance claim and told us a rental car would be waiting once we dropped the vehicle off for repairs.
Unfortunately, that wasn't the case. We were sent to two different Enterprise locations—one in Suffolk and another in Chesapeake—and both told us they had no vehicles available, despite the insurance company assuring us a rental was ready.
Feeling frustrated, I called the Enterprise location at 1636 Military Highway, where I spoke with the manager, Marcus. I explained everything we had been through, and without hesitation he said, "Come here, and I'll have a vehicle for you." When we arrived, he kept his word.
A few days later, the insurance company tried to have us return the rental because they had only authorized a compact car, even though our vehicle was still being repaired at Caliber Collision. We didn't know what to do, so I called Marcus again. Even though it wasn't his responsibility, he took the time to speak directly with the insurance company on our behalf and got everything resolved.
The level of care, professionalism, and genuine concern Marcus showed us was far beyond anything we expected. He went above and beyond to make sure we were taken care of during a stressful situation that was completely out of our control.
Because of Marcus, we will always choose this Enterprise location for our rental needs. Enterprise is incredibly fortunate to have a manager like him. He truly represents what outstanding customer service should look like.
Thank you, Marcus, for everything you did for us. We will never forget your kindness and dedication.
Frequently Asked Questions About Enterprise Rent-A-Car
What types of vehicles does Enterprise Rent-A-Car in Chesapeake offer?
Enterprise Rent-A-Car offers a wide range of vehicles including cars, vans, and luxury cars to suit various rental needs.
Where is Enterprise Rent-A-Car located in Chesapeake, VA?
It is located at 1636 S Military Hwy, Chesapeake, VA 23320, USA.
What are the operating hours for Enterprise Rent-A-Car in Chesapeake?
They are open Monday to Friday from 8:00 AM to 6:00 PM, Saturday from 9:00 AM to 12:00 PM, and closed on Sundays.
Can I make a reservation online for a rental car at this Enterprise location?
Yes, reservations can be made online at their website: https://www.enterprise.com/en/car-rental-locations/us/va/chesapeake-greenbrier-military-21g2.html
What payment methods are accepted at Enterprise Rent-A-Car in Chesapeake?
They accept American Express, Cash, Check, Discover, MasterCard, and Visa.
Does Enterprise Rent-A-Car offer any special discounts for military members?
Yes, they provide discounts for active military personnel.
What nearby dining options are available around Enterprise Rent-A-Car in Chesapeake?
Nearby dining options include Wendy's, New City Chinese Restaurant, Subway, Kervan Kebab House, Burger King, Taco Bell, and Crazy Buffet, offering a variety of fast food, Chinese, Middle Eastern, and other cuisines.
Are there other car rental agencies near this Enterprise Rent-A-Car location?
Yes, nearby you can find Dollar Rent a Car and Hertz for additional car or truck rental options.
What nearby services can customers access while renting from Enterprise Rent-A-Car?
Customers can visit nearby services such as Hampton Roads Smoke Shops, Ambition Barbershop, Greenbrier Florist, and Greenbrier Animal Care Center while in the area.
How can I contact Enterprise Rent-A-Car in Chesapeake?
You can contact them by phone at +1 757-361-0081.
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