$74 Car Rental Chestertown, MD

Search and Compare from Car Companies in Chestertown

Photo by Patricia Knorr
I have a discount code

Featured car rental suppliers

Compare from agencies

car suppliers logo

  • protection illustration

    Change your mind

    Penalty-free cancellation on many/select car rentals
  • trophy illustration

    Treat yourself

    One Key members save 10% or more on over 1 million car rentals
    Learn about One Key
  • package illustration

    Shop smart

    Compare car suppliers and package your flight, hotel, and car to save

Top Car Deals in Chestertown

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

Fri, Nov 21 to Sat, Nov 22

Economy

Hyundai Venue or similar
  • 5 people
  • Unlimited mileage
Aberdeen, District of Columbia, USA
Hyundai Venue

$75

includes taxes & fees
$65 per day
found 2 days ago
Economy Hyundai Venue
Fri, Nov 21 to Sat, Nov 22

Compact

Kia Soul or similar
  • 5 people
  • Unlimited mileage
Aberdeen, District of Columbia, USA
Kia Soul

$75

includes taxes & fees
$65 per day
found 2 days ago
Compact Kia Soul
Fri, Nov 21 to Sat, Nov 22

Midsize SUV

Mazda CX-50 or similar
  • 5 people
  • Unlimited mileage
Middletown, Delaware, USA
Mazda CX-50

$74

includes taxes & fees
$69 per day
found 2 days ago
Midsize SUV Mazda CX-50
Fri, Nov 21 to Sat, Nov 22

Standard

Volkswagen Jetta or similar
  • 5 people
  • Unlimited mileage
Aberdeen, District of Columbia, USA
Volkswagen Jetta

$79

includes taxes & fees
$69 per day
found 2 days ago
Standard Volkswagen Jetta
Fri, Nov 21 to Sat, Nov 22

Fullsize

Toyota Camry or similar
  • 5 people
  • Unlimited mileage
Aberdeen, District of Columbia, USA
Toyota Camry

$79

includes taxes & fees
$69 per day
found 2 days ago
Fullsize Toyota Camry
Fri, Nov 21 to Sat, Nov 22

Standard Elite SUV

Ford Explorer or similar
  • 7 people
  • Unlimited mileage
Aberdeen, District of Columbia, USA
Ford Explorer

$91

includes taxes & fees
$80 per day
found 2 days ago
Standard Elite SUV Ford Explorer
Fri, Nov 21 to Sat, Nov 22

Luxury

Cadillac CT5 or similar
  • 5 people
  • Unlimited mileage
Aberdeen, District of Columbia, USA
Cadillac CT5

$94

includes taxes & fees
$82 per day
found 2 days ago
Luxury Cadillac CT5
Fri, Nov 21 to Sat, Nov 22

Premium

Toyota Crown or similar
  • 5 people
  • Unlimited mileage
Aberdeen, District of Columbia, USA
Toyota Crown

$97

includes taxes & fees
$85 per day
found 2 days ago
Premium Toyota Crown
Fri, Nov 21 to Sat, Nov 22

Mini Van

Chrysler Pacifica or similar
  • 7 people
  • Unlimited mileage
Aberdeen, District of Columbia, USA
Chrysler Pacifica

$100

includes taxes & fees
$88 per day
found 2 days ago
Mini Van Chrysler Pacifica

Don't see what you're looking for?

See all car rentals in Chestertown
View all cars
Lowest prices found within the past 2 days. 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 $74 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?
Canceling 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.
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 55 miles 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 60 miles from Chestertown.
  • Battery Park is located 150 miles 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 license 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 $74 and $75. 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.
What insurance should I choose for my car rental in Chestertown?
For a safe, stress-free road trip, add Expedia's collision damage protection to your rental car booking. This insurance covers your ride against vandalism, accident damage and theft. It also offers 24-hour emergency support in times of need. Opt in to this insurance while finalizing your Chestertown vehicle with Expedia and save time and money at the rental desk.

Car Rental Information

 
Popular car types
SUV, Full Size, Economy
 
Car suppliers available
 
Our best deal of the day
$74
 
Our second best deal of the day
$75
 
Our third best deal of the day
$79
 
From the airport to your hotel
Airport Transportation
 
From popular domestic and international airports
Airport Car Rentals

Finding the cheapest car rentals in Chestertown

Using our Search Wizard

If the deals that are available on our page do not suit your needs, then enter Chestertown into the search wizard at the top of the page. We will compare all the best deals available for your car rental in Chestertown and provide you with a list of the cheapest options, with no added fees.

Renting a car in Chestertown

Pay at pickup is available, so you don’t have to worry about spending your money until you arrive at your vehicle in Chestertown. We partner with reliable partners that guarantee an enjoyable experience for solo travelers, couples, and families. Package your car with a flight or hotel to unlock even more savings from Expedia.

Expected prices in Chestertown

Prices are subject to seasonal change depending on when you decide to arrange your car rental but right now you can book from $74.

Flexibility & Cancellation

Most car suppliers offer penalty-free cancellations, so you don’t have to worry about losing money if your plans change. To cancel your booking log into your account through the Trips portal. Click manage booking and cancel this car. If you needed to alter your booking, then you can create a new one once you have canceled.

We all love being rewarded

One Key members save 10% or more on select hotels, cars, activities and vacation rentals. Not only that, earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands: Expedia, Hotels.com and VRBO. Learn more and join today.

Car classes available from Expedia in 2025

The classes of vehicles available will change depending on your chosen location.

Explore a world of travel with Expedia