Trailer Rental & Towing in Chestertown, MD at Chesapeake Outdoor Structures

Moving to or from Chestertown, MD? U-Haul cargo and enclosed trailers are intelligently designed to protect and secure your precious belongings, while our open utility trailers are perfect for hauling building supplies, landscaping materials or bulky items. U-Haul car trailers have EZ load ramps for effortless loading of vehicles while our motorcycle trailers are lightweight and easy to tow. Get FREE trailer rental rate quotes in Chestertown MD 21620 today.

Get FREE trailer rental quotes on car trailers, utility trailers, cargo trailers, and motorcycle trailer rentals in Chestertown, MD

Cargo Trailers

Cargo trailers in Chestertown, MD are lightweight, aerodynamic, and engineered for better fuel economy which makes it easy to tow behind any vehicle. Millions of families use our enclosed cargo trailers to move every year. U-Haul has a large selection of enclosed trailers to rent in-town or one way, review our cargo trailer sizes and reserve a trailer rental online at Chesapeake Outdoor Structures!

Utility Trailers

Utility trailers are perfect for towing large or oversize cargo in Chestertown MD 21620. Many utility trailer rentals come equipped with a loading ramp for easy convenience. The utility trailer selection at Chesapeake Outdoor Structures provides an affordable solution for home improvement projects, furniture delivery and for towing recreational vehicles. Utility trailer rentals are also popular with businesses for deliveries and trade-show events. Utility trailers come in a wide range of sizes and styles so that any car can tow.

Car Trailers

Moving cross-country with your vehicle on a car trailer is a smart way to save gas and eliminate miles of wear and tear on your vehicle. Our Tow Dolly is a low-cost option for towing front wheel drive vehicles, while auto transports are ideal for long distance moves. Both car haulers fit most sized vehicles in Chestertown, MD and are also an economical alternative to calling a tow truck in the case of a break-down. Whether towing behind a U-Haul moving van or your own personal vehicle, you can rent a car hauler for both in-town and one way moves.

Motorcycle Trailers

Motorcycle trailers in are lightweight, easy to tow and have an easy-access loading ramp. Each motorcycle trailer also comes equipped with an integrated chock for the front wheel and with heavy-duty tie-down rings to support even the heaviest of motorcycles. Reserve your motorcycle trailer rental in Chestertown, MD online today!

Trailer and Towing Supplies

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Wiring and lights

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Customer Reviews

David S. on


The agent was extremely helpful and accommodating.

Donald M. on


Keep everything the way it is, great customer service.

Paula R. on


Great, friendly service!

George B. on


Place was closed during normal business hours

Edgar T. on


GPS takes you down the road a bit but it is the first business that you come to.

Chris M. on


It was a seamless experience. From start to finish. From phone call to pick up to drop off. Great experience

John O. on


Excellent customer service and support

Paul S. on


Everything went as I expected. Thank you for making it a problem-less occasion.

Doyal A. on


nothing that i can thing of.

Jeffrey B. on


Equipment was great, service was excellent price was fair I will definitely use this location again

Raymond L. on


keep up the great work

Kenneth w. on


Bruce is personable and professional and makes the process easy.

Matthew H. on


Bruce went above and beyond to safely connect our trailer. He is a gentleman and a businessman. We will be doing business here again.

William W. on


Bruce was very helpful and responded to our rental need in just 15 minutes.

William F. on


Everything was great - manager was very helpful. Thanks!

Hector O. on


Bruce the owner, is a great guy, he goes out of his way to accommodate his customers. Way better than Brooklyn Uhaul center.

Andrew R. on


Easy drop off

Roy B. on


Really a pleasure to work with this manager!

John E. on


After hours drop off, so no personnel on hand. I got my check-in email promptly in the morning.

Richard S. on


The car transport was excellent and worked perfectly for all of my needs. No problems at all. Mr. Coleman was professional and very helpful. Thank you for supplying me with the proper equipment from U-Haul.

Blanche T. on


Nothing I can think of. The agent Bruce was very personable and efficient

Tracy H. on


Great job! Bruce is always easy to work with!

Heather J. on


Bruce was very polite & made me feel welcome by having conversation as he typed up the paperwork. Due to a problem with the storage unit company, I had thought I may be a little late, so I called him & he was very helpful with that situation. I would definitely rent from him again & will recommend him to my family & friends for their UHaul needs!!!! THANK YOU MR. BRUCE!!!!

Robert S. on


The location was fine and the staff was excellent, but I did not get the truck I reserved at the location I preferred. Your concept of the word “reservation” is misleading and made my move much more difficult than needed.

William B. on


Great customer service. Excellent vehicle.

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