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Chestertown car rentals

KAYAK compares hundreds of rental car sites at once for car rental deals in Chestertown, Maryland

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Cheap car rentals in Chestertown

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Mini
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Economy car
Economy
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Compact car
Compact
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Intermediate car
Intermediate
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Standard car
Standard
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Full-size car
Full-size
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Luxury car
Luxury
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KAYAK’s top tips for renting a car in Chestertown

  • 25% of our users found rental cars in Chestertown for $40 or less

FAQs about renting a car in Chestertown

  • How much does it cost to rent a car in Chestertown?

    On average a rental car in Chestertown costs $61 per day. But prices differ between operators and you can save money through a price comparison of car rental deals from different agencies. The cheapest price for a car rental in Chestertown found in the last 2 weeks is $61.

  • How much is gas price in Chestertown?

    The average gas price in Chestertown is $3.40 per gallon over the past 30 days. Filling up a gas tank costs between $41 and $54, depending on the car size.

  • What is the most popular rental car in Chestertown?

    Full-size (Chevrolet Tahoe or similar) is the most frequently booked rental car type in Chestertown.

  • Which car rental companies will pick you up at Baltimore/Washington airport (BWI)?

    The only car rental company that offers shuttle or pick-up services from Baltimore/Washington airport to off-airport locations is NextCar.

  • How can I find car rentals near me in Chestertown?

    Take a look at our extensive car rental location map to find the best rental cars near you.

  • How much does a Full Size car rental cost in Chestertown?

    A Full Size car rental in Chestertown costs $84 per day, on average.

  • Should I get insurance when renting a car in Chestertown?

    Most car rental providers in Chestertown offer insurance but the level of protection can differ substantially. If you're unsure whether to get extra protection for your car rental in Chestertown, check out KAYAK's car rental insurance guide.

  • How many car agencies are operating in Chestertown?

    KAYAK has deals for you to compare from 2 car rental agencies in Chestertown.

  • What do I need to know before booking a car rental in Chestertown?

    Finding the right price, understanding the add-ons and staying up to date with policy changes can be a challenge. That’s why KAYAK has produced the ultimate guide to renting a car to help you cut though the jargon and make the right choice for your rental car. Find tips and insights for how to book your rental, what car rental insurance you’ll need, how to deal with a car rental agency and what extra fees to expect (and avoid!).

  • Why should I use KAYAK to rent a car in Chestertown?

    KAYAK searches thousands of car rental agencies to provide you with offers from all car rental agencies operating in Chestertown so that you can compare car rental rates, reviews and pick-up and drop-off locations to find the best deal for you.

See more FAQs

Chestertown car rental reviews and directory 
All ratings and reviews are collected from KAYAK users with a verified car rental booking. Learn how KAYAK collects reviews.

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4.6

Mediocre

Best rated

One location in Chestertown

Show locations

Locations in Chestertown

6407 Churchhill Rd Chestertown

Opening times not available

Filters

No reviews available

Enterprise Rent-A-Car

No score available yet

Cheapest deal
Most popular

5 locations in Chestertown

Show locations

Locations in Chestertown

121 Flatland Rd

+1 410 829 6202

Monday00:00 - 00:00
Tuesday00:00 - 00:00
Wednesday00:00 - 00:00
Thursday00:00 - 00:00
Friday00:00 - 00:00
Saturday00:00 - 00:00
Sunday00:00 - 00:00

1418 Main St

+1 410 604 6154

Monday07:30 - 17:00
Tuesday07:30 - 17:00
Wednesday07:30 - 17:00
Thursday07:30 - 17:00
Friday07:30 - 17:00
Saturday00:00 - 00:00
Sunday00:00 - 00:00

1601 Eastern Blvd

+1 410 682 6474

Monday07:30 - 17:00
Tuesday07:30 - 17:00
Wednesday07:30 - 17:00
Thursday07:30 - 17:00
Friday07:30 - 17:00
Saturday09:00 - 14:00
Sunday00:00 - 00:00

2103 Pulaski Hwy

+1 410 671 6305

Monday07:30 - 17:00
Tuesday07:30 - 17:00
Wednesday07:30 - 17:00
Thursday07:30 - 17:00
Friday07:30 - 17:00
Saturday00:00 - 00:00
Sunday00:00 - 00:00

983 Beards Hill Rd

+1 410 273 7711

Monday07:30 - 17:00
Tuesday07:30 - 17:00
Wednesday07:30 - 17:00
Thursday07:30 - 17:00
Friday07:30 - 17:00
Saturday09:00 - 14:00
Sunday00:00 - 00:00

Filters

Reviews

8.0 Very good

Anonymous, Sep 2022

KAYAK
n/a

1 out of 1

Hertz

No score available yet

2 locations in Chestertown

Show locations

Locations in Chestertown

1121 South Philadelphia Blvd

+1 410 272 2813

Monday08:00 - 17:00
Tuesday08:00 - 17:00
Wednesday08:00 - 17:00
Thursday08:00 - 17:00
Friday08:00 - 17:00

403a Baltimore Pike

+1 239 207 8878

Monday08:00 - 17:00
Tuesday08:00 - 17:00
Wednesday08:00 - 17:00
Thursday08:00 - 17:00
Friday08:00 - 17:00
Saturday09:00 - 14:00

Filters

No reviews available

Avis

No score available yet

One location in Chestertown

Show locations

Locations in Chestertown

609 South Philadelphia Blvd

+1 410 575 7279

Monday08:00 - 17:00
Tuesday08:00 - 17:00
Wednesday08:00 - 17:00
Thursday08:00 - 17:00
Friday08:00 - 17:00
Saturday08:00 - 17:00
Sunday10:00 - 16:00

Filters

No reviews available

Budget

No score available yet

One location in Chestertown

Show locations

Locations in Chestertown

609 South Philadelphia Blvd

+1 410 272 2781

Monday08:00 - 17:00
Tuesday08:00 - 17:00
Wednesday08:00 - 17:00
Thursday08:00 - 17:00
Friday08:00 - 17:00
Saturday08:00 - 17:00
Sunday10:00 - 16:00

Filters

Reviews

2.0 Poor

Anonymous, Dec 2024

Passenger van

KAYAK
Sadly, the customer service was horrible; Mary didn't know how to properly respond to a customer or troubleshoot; instead, she made it very clear that the manager was on vacation and there was nothing she could do to rectify the situation.I get it; it's a busy time of year; however, it's not what you say; it's how you say it. Extremely Rude. If a person is unhappy or miserable dealing with customers and a safety issue, you shouldn't be dealing with or working in customer service. Budget rented a passenger van; from a safety perspective, you should always make sure everything is operating effectively and safely and, most importantly, be able to communicate without being insensitive. The van door wasn't closing properly; out of nowhere, the van was shaking on and off, and for some odd reason, it should be the renter's issue. Please help me understand; we did everything correctly. We called, spoke with Mary, and reported the issue slightly after 8 am on Saturday, December 21, 2025. She was supposed to document the account; she insisted she was documenting, however she didn't. 

1 out of 1

Car rental locations in or near Chestertown

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Traveling to a place near Chestertown?

Rent a car at Chestertown if you plan to visit one of these locations
Grasonville
Camp Springs
Chesapeake Beach
Colonial Beach
Hunt Valley
Mount Rainier
Essex
Falmouth
Shrewsbury
Chester
Somerset
Dunkirk
Oxford
White Plains
Cordova

Good to know

Most popular agency

Enterprise Rent-A-Car

Most popular car type

Full-size

Average price

$61/day

Good deal

$40/day

When to book a rental car in Chestertown

Average daily price per month
Rental car prices as pick-up date approaches

Everything you need to know for your car rental in Chestertown

Chestertown car rental information

Pick-up locationChestertown
Car types
Rental locations2
Airport locations0

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