Chestertown car rentals

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Car Rental Deals

Cheap car rentals in Chestertown

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Small car
Small
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Medium car
Medium
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Large car
Large
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Luxury car
Luxury
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Van car
Van
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SUV car
SUV
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Commercial car
Commercial
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Pickup truck car
Pickup truck
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Booking Insights

Good to know

Most popular agency

Average price

Good deal

Enterprise Rent-A-Car
$81/day
$81/day

KAYAK’s insights & trends for Chestertown car rentals

Check out the latest trends and booking tips to rent a car in Chestertown with confidence.

What is the best rental car company in Chestertown?

Based on ratings and reviews from real users on KAYAK, the best car rental companies in Chestertown are U-Save (4.5), Global Rent A Car (2.0), and Enterprise Rent-A-Car (0.0, 1 review).
U-Save
U-Save
Rated 4.5/10
Global Rent A Car
Global Rent A Car
Rated 2.0/10
Enterprise Rent-A-Car
Enterprise Rent-A-Car
Rated 0.0/10
Hertz
Hertz
Rated 0.0/10

What is the cheapest month to rent a car in Chestertown?

The cheapest month to rent a car in Chestertown is March at an average cost of $40/day. June is the most expensive month to rent a car in Chestertown when prices are $129/day on average, which tends to be 81% above the yearly average rental price for Chestertown.

What rental car company in Chestertown has the most locations?

Enterprise Rent-A-Car operates 4 locations in Chestertown, more than any other rental company.
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KAYAK’s top tips for renting a car in Chestertown

  • 25% of our users found rental cars in Chestertown for $81 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 $81 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 $81.

  • Which car rental companies are at Baltimore/Washington airport (BWI)?

    The only car rental company onsite at Baltimore/Washington airport is Hertz.

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

    Car rental companies that offer shuttle or pick-up services from Baltimore/Washington airport to off-airport locations include NextCar, and Hertz.

  • 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.

  • 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 3 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.

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.

U-Save

4.5

Mediocre

One location in Chestertown

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Locations in Chestertown

6407 Churchhill Rd Chestertown

Opening times not available

Filters

No reviews available

Global Rent A Car

2.0

Poor

One location in Chestertown

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Locations in Chestertown

6407 Churchhill Rd

Opening times not available

Filters

No reviews available

Enterprise Rent-A-Car

No score available yet

4 locations in Chestertown

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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

Filters

No reviews available

Hertz

No score available yet

2 locations in Chestertown

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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

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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

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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
Colonial Beach
Hunt Valley
Camp Springs
Chesapeake Beach
Essex
Shrewsbury
Falmouth
Chester
Mount Rainier
Somerset
Oxford
White Plains
Dunkirk
Cordova

Everything you need to know for your car rental in Chestertown

Chestertown car rental information

Pick-up locationChestertown
Car types
Rental locations3
Airport locations0

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