Title: CA $104 Car Rental with Enterprise at 121 Flatland Rd, Chestertown - Expedia.ca - ![protection illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__protection.svg) ### Change your mind Penalty-free cancellation on many/select car rentals - ![trophy illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__trophy.svg) ### Treat yourself Members save 10% or more on over 1 million car rentals - ![package illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__package.svg) ### Shop smart Compare car suppliers to unlock big savings ## Find Cheap Enterprise Rental Deals in 121 Flatland Rd 21620, Chestertown \* Price found within the past 6 days. Click for updated prices. Mon, Dec 8 - Tue, Dec 9 ### Compact 2/4 Door Car Nissan Versa or similar or similar - 5 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) Chestertown, Maryland, USA ![Nissan Versa or similar](https://mediaim.expedia.com/cars/15/c84a49c1-ffbe-466e-90ad-8aab89447e55.jpg?impolicy=resizecrop&ra=fit&rh=165&rw=165) #### CA $104 total found 0 minutes ago [](https://expedia.ca/carsearch?olat=39.219768&olon=-76.08272&totalprice=104.00¤cy=CAD&date1=08/12/2025&date2=09/12/2025&clientrfrr=CarMarketingLandingPages&tprfrr=104.00&cvrfrr=ET&ctrfrr=CC&piid=AQkwSF_NHd_GKkI7QCbCnsLLavjCnI7in9MF41jMKsvok4TIvgrO3Ti8EAOPb0L88oPTj0v3Y0kxl5VVC5WSnEKaPreiCLzQDPViGc548dpfA&selCC=[%22compact%22]) Mon, Dec 8 - Tue, Dec 9 ### Economy 2/4 Door Car Mitsubishi Mirage or similar or similar - 4 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) Chestertown, Maryland, USA ![Mitsubishi Mirage or similar](https://mediaim.expedia.com/cars/15/a148d8a9-c2f8-4a17-9578-33ccabb2e3b2.jpg?impolicy=resizecrop&ra=fit&rh=165&rw=165) #### CA $104 total found 0 minutes ago [](https://expedia.ca/carsearch?olat=39.219768&olon=-76.08272&totalprice=104.00¤cy=CAD&date1=08/12/2025&date2=09/12/2025&clientrfrr=CarMarketingLandingPages&tprfrr=104.00&cvrfrr=ET&ctrfrr=EC&piid=AQkwSF_NHd_GKkI7QCbCnsLLavjCnI7in9MF41jMKsvok4TIvgrO3Ti8EAOPb0L88o0psb2RHXKxkHjOul6dL0laPreiCLzQDPViGc548dpfA&selCC=[%22economy%22]) Mon, Dec 8 - Tue, Dec 9 ### Standard Pickup Regular Cab Toyota Tacoma or similar or similar - 5 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) Chestertown, Maryland, USA ![Toyota Tacoma or similar](https://mediaim.expedia.com/cars/15/49328ee2-ef9e-4994-957d-befbb9e44880.jpg?impolicy=resizecrop&ra=fit&rh=165&rw=165) #### CA $106 total found 0 minutes ago [](https://expedia.ca/carsearch?olat=39.219768&olon=-76.08272&totalprice=106.24¤cy=CAD&date1=08/12/2025&date2=09/12/2025&clientrfrr=CarMarketingLandingPages&tprfrr=106.24&cvrfrr=ET&ctrfrr=SP&piid=AQkwSF_NHd_GKkI7QCbCnsLLavjCnI7in9MF41jMKsvok4TIvgrO3Ti8EAOPb0L88oSN8DReRry-UP9x76gyCRkqPreiCLzQDPViGc548dpfA&selCC=[%22pickup%22]) Mon, Dec 8 - Tue, Dec 9 ### Midsize 2/4 Door Car Toyota Corolla or similar or similar - 5 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) Chestertown, Maryland, USA ![Toyota Corolla or similar](https://mediaim.expedia.com/cars/15/2fb42efc-d702-4422-a3ff-39598ece9fc3.jpg?impolicy=resizecrop&ra=fit&rh=165&rw=165) #### CA $107 total found 0 minutes ago [](https://expedia.ca/carsearch?olat=39.219768&olon=-76.08272&totalprice=107.08¤cy=CAD&date1=08/12/2025&date2=09/12/2025&clientrfrr=CarMarketingLandingPages&tprfrr=107.08&cvrfrr=ET&ctrfrr=IC&piid=AQkwSF_NHd_GKkI7QCbCnsLLavjCnI7in9MF41jMKsvok4TIvgrO3Ti8EAOPb0L88o0-SGzcA-9Z-sHhDMevlGY6PreiCLzQDPViGc548dpfA&selCC=[%22midsize%22]) Mon, Dec 8 - Tue, Dec 9 ### Compact SUV Hyundai Kona or similar or similar - 5 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) Chestertown, Maryland, USA ![Hyundai Kona or similar](https://mediaim.expedia.com/cars/15/b828723f-a6cd-47c4-98fb-c7e77ff9fe86.jpg?impolicy=resizecrop&ra=fit&rh=165&rw=165) #### CA $110 total found 0 minutes ago [](https://expedia.ca/carsearch?olat=39.219768&olon=-76.08272&totalprice=109.75¤cy=CAD&date1=08/12/2025&date2=09/12/2025&clientrfrr=CarMarketingLandingPages&tprfrr=109.75&cvrfrr=ET&ctrfrr=CF&piid=AQkwSF_NHd_GKkI7QCbCnsLLavjCnI7in9MF41jMKsvok4TIvgrO3Ti8EAOPb0L88oCXSocytDE-1srEaEjXgS2KPreiCLzQDPViGc548dpfA&selCC=[%22suv%22]) Mon, Dec 8 - Tue, Dec 9 ### Fullsize 2/4 Door Car Chevrolet Malibu or similar or similar - 5 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) Chestertown, Maryland, USA ![Chevrolet Malibu or similar](https://mediaim.expedia.com/cars/15/e98a0840-512d-4fa0-9d47-d2f164abb795.jpg?impolicy=resizecrop&ra=fit&rh=165&rw=165) #### CA $110 total found 0 minutes ago [](https://expedia.ca/carsearch?olat=39.219768&olon=-76.08272&totalprice=110.16¤cy=CAD&date1=08/12/2025&date2=09/12/2025&clientrfrr=CarMarketingLandingPages&tprfrr=110.16&cvrfrr=ET&ctrfrr=FC&piid=AQkwSF_NHd_GKkI7QCbCnsLLavjCnI7in9MF41jMKsvok4TIvgrO3Ti8EAOPb0L88oZLwc9LFcT-oWG8-Fa-DqLKPreiCLzQDPViGc548dpfA&selCC=[%22fullsize%22]) Mon, Dec 8 - Tue, Dec 9 ### Standard 2/4 Door Car Volkswagen Jetta or similar or similar - 5 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) Chestertown, Maryland, USA ![Volkswagen Jetta or similar](https://mediaim.expedia.com/cars/15/a91881fc-ef2d-44c7-a02d-e27a292968d5.jpg?impolicy=resizecrop&ra=fit&rh=165&rw=165) #### CA $110 total found 0 minutes ago [](https://expedia.ca/carsearch?olat=39.219768&olon=-76.08272&totalprice=110.16¤cy=CAD&date1=08/12/2025&date2=09/12/2025&clientrfrr=CarMarketingLandingPages&tprfrr=110.16&cvrfrr=ET&ctrfrr=SC&piid=AQkwSF_NHd_GKkI7QCbCnsLLavjCnI7in9MF41jMKsvok4TIvgrO3Ti8EAOPb0L88odhxBiiZ5VvBWiZMgz3dkm6PreiCLzQDPViGc548dpfA&selCC=[%22standard%22]) Mon, Dec 8 - Tue, Dec 9 ### Premium Pickup Regular Cab Ford F150 or similar or similar - 5 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) Chestertown, Maryland, USA ![Ford F150 or similar](https://mediaim.expedia.com/cars/15/6d28e269-3461-482a-90d2-4786c2de3e1f.jpg?impolicy=resizecrop&ra=fit&rh=165&rw=165) #### CA $114 total found 0 minutes ago [](https://expedia.ca/carsearch?olat=39.219768&olon=-76.08272&totalprice=113.70¤cy=CAD&date1=08/12/2025&date2=09/12/2025&clientrfrr=CarMarketingLandingPages&tprfrr=113.70&cvrfrr=ET&ctrfrr=PP&piid=AQkwSF_NHd_GKkI7QCbCnsLLavjCnI7in9MF41jMKsvok4TIvgrO3Ti8EAOPb0L88oi_xTsJ9_q49Hul0IttB9tKPreiCLzQDPViGc548dpfA&selCC=[%22pickup%22]) ### Don't see what you're looking for? See all car rentals in 121 Flatland Rd [View all cars](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&locn=Enterprise%20-%20121%20Flatland%20Rd,%20Chestertown,%20Maryland&date1=14/12/2025&date2=16/12/2025&crfrr=defaultFlex&selVen=[%2215%22]) ## This Enterprise pickup location details in Chestertown: **Enterprise** 121 Flatland Rd Chestertown, MD 21620 USA