Chestertown Car Rental

Search and Compare from Car Companies in Chestertown

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

Top Car Deals in Chestertown

* Price found within the past 6 days. Click for updated prices.

Tue., Aug. 19 to Wed., Aug. 20

Compact

Nissan Versa or similar
  • 5 people
  • Unlimited mileage
Chestertown, Maryland, USA
Nissan Versa

CA $96

total
found 4 hours ago
Compact Nissan Versa
Tue., Aug. 19 to Wed., Aug. 20

Economy

Mitsubishi Mirage or similar
  • 4 people
  • Unlimited mileage
Chestertown, Maryland, USA
Mitsubishi Mirage

CA $96

total
found 4 hours ago
Economy Mitsubishi Mirage
Tue., Aug. 19 to Wed., Aug. 20

Midsize

Toyota Corolla or similar
  • 5 people
  • Unlimited mileage
Chestertown, Maryland, USA
Toyota Corolla

CA $99

total
found 4 hours ago
Midsize Toyota Corolla
Tue., Aug. 19 to Wed., Aug. 20

Standard

Volkswagen Jetta or similar
  • 5 people
  • Unlimited mileage
Chestertown, Maryland, USA
Volkswagen Jetta

CA $102

total
found 4 hours ago
Standard Volkswagen Jetta
Tue., Aug. 19 to Wed., Aug. 20

Full Size

Chevrolet Malibu or similar
  • 5 people
  • Unlimited mileage
Chestertown, Maryland, USA
Chevrolet Malibu

CA $102

total
found 4 hours ago
Full Size Chevrolet Malibu
Tue., Aug. 19 to Wed., Aug. 20

Premium Pickup Regular Cab

Ford F150 or similar
  • 5 people
  • Unlimited mileage
Chestertown, Maryland, USA
Ford F150

CA $115

total
found 4 hours ago
Premium Pickup Regular Cab Ford F150
Tue., Aug. 19 to Wed., Aug. 20

Luxury

Audi A4 or BMW 3 Series or similar
  • 5 people
  • Unlimited mileage
Chestertown, Maryland, USA
Audi A4 or BMW 3 Series

CA $127

total
found 4 hours ago
Luxury Audi A4 or BMW 3 Series

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Lowest prices found within the past 4 hours. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much is a rental car per day in Chestertown?
Daily rental prices were as low as CA $96 within the past seven days. With rates like this, cruising the streets of Chestertown in your own set of wheels is an affordable and convenient way to visit the sights.
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.

Why should I rent a Chestertown car with Expedia?
With years of experience finding the lowest prices for adventurers around the globe, Expedia is the ideal place to rent your car. We have suppliers in Chestertown to take your pick of, offering everything from zippy compacts to spacious SUVs. Why not combine your car with your hotel and flights and save more? From our vacation packages to our member prices and exclusive offers, Expedia will get you on your way for less.
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.
What is the cheapest car rental in Chestertown?
The two lowest daily rates offered in Chestertown within the past seven days were CA $96 and CA $99. Now that's what we'd call a fantastic deal! These rates were available on Expedia, with a rental starting date within the next year. Prices and availability are subject to change and additional terms apply.
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-vacation. 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.

Car Rental Information

Popular car types:
SUV, Full Size, Economy
Car suppliers available:
Our best deal of the day:
CA $96
Our second best deal of the day:
CA $99
Our third best deal of the day:
CA $102
From the airport to your hotel:
Airport Transportation