Chestertown Car Rental

Search and Compare from Car Companies in Chestertown

Photo by Patricia Knorr

Compare car suppliers to unlock big savings, and package your flight, hotel, and car to save even more.

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Enjoy maximum flexibility with penalty-free cancellation on most car rentals.

Frequently asked questions

What happens if I need to cancel my Chestertown car reservation?
Cancelling a prepaid car booking at least six hours before pickup should allow for a total refund. However, this is not always guaranteed. It's a good idea to scan your itinerary and rental agreement. Still can't find the answer? Hop on our Customer Service Portal.
What types of cars can I rent in Chestertown?
Dart around in a mini, style it up in a premium ride or choose something in the middle, like a mid-size. But it's hard to go past a compact vehicle — the top pick in Chestertown. They're a snap to handle and park, fuel-efficient and an excellent idea if you're cruising around busy cities. An upgrade from economy, you can expect a little more comfort and room at a price that's still nice.
Where can I go on a road trip from Chestertown?
After you've ticked off the amazing sights in Chestertown, there's plenty more to see in the surrounding region. Grab the keys to a rental car, pack your bags in the trunk and get out on the open road. We've pulled together some drives we're confident you'll love:

  • Washington is around 88 kilometres from Chestertown. Famous tourist attractions like White House should be at the top of your list here.
  • Why not see everything on offer in Alexandria too? Major sights here include George Washington Masonic National Memorial. Alexandria is 97 kilometres from Chestertown.
  • Battery Park is located 241 kilometres from Chestertown and is one of the region's most gorgeous nature spots. Go for a wander around and enjoy the fresh air here.

How do I find the best car rental deals in Chestertown with Expedia?
Browse our huge selection of rental cars, check out customer ratings and compare prices from big-name brands. In a few simple clicks, Expedia will help you find the best deal on your wheels. Got a hotel or flight booking? Add on your Chestertown car rental to save even more.
How old do you have to be to rent a car in Chestertown?
If you're aged 21 and over, you can rent a car in Chestertown. Be mindful that rental companies will charge an extra fee if you're a young driver, which helps cover the higher damage risk involved. Also, young drivers are often restricted from renting specialty or luxury vehicles. Thoroughly read the terms and conditions before booking so there are no surprises when it's time to collect the keys.
What do you need to rent a car in Chestertown?
Two things — your driver's licence and a credit card in your name. Many car rental companies will offer you insurance, which is optional. But you may be asked to provide proof of other coverage if you opt out. We recommend checking with your supplier to avoid any problems.
Can I rent a car for a month or longer in Chestertown?
Yes, which means you won't have to rebook a rental vehicle mid-holiday. Head over to our long-term car rental deals page, enter your travel dates and find a ride that's all yours for however long you need.
Where can I find a Chestertown car rental if I am younger than 25?
You'll need to look into the age policy of the Chestertown rental suppliers you're interested in. If you're under 25 years of age, be aware that some will charge additional fees. It's better to know this in advance so you can plan your budget accordingly. Each rental car company has its own rules for younger drivers, so do your research.