$62 Car Rental Chestertown, MD

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Top Car Deals in Chestertown

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

Midsize

Toyota Corolla
  • 5 people
  • Unlimited mileage
MIDDLETOWN, USA
Toyota Corolla

$62

includes taxes & fees
$57 per day
found 2 days ago
Midsize Toyota Corolla

Fullsize

Toyota Camry
  • 5 people
  • Unlimited mileage
Middletown, Delaware, USA
Toyota Camry

$64

includes taxes & fees
$59 per day
found 2 days ago
Fullsize Toyota Camry

Standard

Volkswagen Jetta
  • 5 people
  • Unlimited mileage
Middletown, Delaware, USA
Volkswagen Jetta

$64

includes taxes & fees
$59 per day
found 2 days ago
Standard Volkswagen Jetta

Economy

Chevrolet Spark
  • 4 people
  • Unlimited mileage
ABERDEEN, USA
Chevrolet Spark

$72

includes taxes & fees
$62 per day
found 11 hours ago
Economy Chevrolet Spark

Compact

Kia Soul
  • 5 people
  • Unlimited mileage
ABERDEEN, USA
Kia Soul

$72

includes taxes & fees
$62 per day
found 11 hours ago
Compact Kia Soul

Standard Elite Special

Ford Mustang Mach-E
  • 5 people
  • Unlimited mileage
Aberdeen, District of Columbia, USA
Ford Mustang Mach-E

$74

includes taxes & fees
$64 per day
found 11 hours ago
Standard Elite Special Ford Mustang Mach-E

Special

Mystery Car May Be Gas Hybrid or EV
  • 3 people
  • Unlimited mileage
Aberdeen, District of Columbia, USA
Mystery Car May Be Gas Hybrid or EV

$79

includes taxes & fees
$68 per day
found 11 hours ago
Special Mystery Car May Be Gas Hybrid or EV

Mini Van

Chrysler Pacifica
  • 7 people
  • Unlimited mileage
BALTIMORE, USA
Chrysler Pacifica

$82

includes taxes & fees
$71 per day
found 11 hours ago
Mini Van Chrysler Pacifica

Premium Pickup Regular Cab

Ford F150 4WD
  • 5 people
  • Unlimited mileage
MIDDLE RIVER, USA
Ford F150 4WD

$84

includes taxes & fees
$76 per day
found 11 hours ago
Premium Pickup Regular Cab Ford F150 4WD

Luxury

Audi A4 Genesis G70 BMW 3 series
  • 5 people
  • Unlimited mileage
Chester, Maryland, USA
Audi A4  Genesis G70  BMW 3 series

$170

includes taxes & fees
$150 per day
found 11 hours ago
Luxury Audi A4 Genesis G70 BMW 3 series

Premium Elite SUV

Audi Q5 Genesis GV70 BMW X3
  • 5 people
  • Unlimited mileage
MIDDLE RIVER, USA
Audi Q5  Genesis GV70  BMW X3

$170

includes taxes & fees
$150 per day
found 11 hours ago
Premium Elite SUV Audi Q5 Genesis GV70 BMW X3

Fullsize Elite Special

Audi A5 Sportback
  • 5 people
  • Unlimited mileage
MIDDLE RIVER, USA
Audi A5 Sportback

$270

includes taxes & fees
$240 per day
found 11 hours ago
Fullsize Elite Special Audi A5 Sportback

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Lowest prices found within the past 2 days. Prices and availability subject to change. Additional terms may apply.

What you need to know for your Chestertown car rental

Reasons to book a car rental in and around Chestertown

Renting a car in Chestertown provides the freedom and flexibility to explore the city and its surroundings at your own pace. With a rental vehicle, you can conveniently visit key attractions like the Historical Society of Kent County Maryland and River Arts Chestertown, both offering rich cultural experiences. For outdoor enthusiasts, Wilmer Park is an ideal spot for family outings and enjoying nature. A car rental also makes it easy to explore nearby towns such as Worton, just 4 miles away, where you can discover Kinnairds Point Drive and Still Pond Station Park. Additionally, Georgetown and Tolchester Beach offer scenic views and recreational opportunities, including Rock Hall Harbor and Sandy Point State Park. Having a car allows for easy luggage management and the flexibility to tailor your travel plans, making it an excellent choice for families, solo travelers, or anyone looking to embrace the scenic beauty and outdoor experiences around Chestertown. Whether you are interested in culture, nature, or simply enjoying the local scenery, a rental car enhances your trip by ensuring you can access all that the area has to offer.

Top rated car suppliers in Chestertown

  • Enterprise: Enterprise is the most popular car rental supplier in Chestertown, featuring one rental location. Travelers frequently choose Enterprise for its excellent customer service and a wide selection of vehicles. The Midsize SUV and Compact cars are among the most booked options, providing flexibility and comfort for your travels. With the ability to manage your itinerary and luggage easily, Enterprise stands out as a reliable choice for exploring Chestertown and its surrounding areas.

Where to stay in and around Chestertown

  • Worton: Located 4 miles from Chestertown, Worton is a great choice for those seeking outdoor experiences and beautiful scenery. Visitors can enjoy Kinnairds Point Drive and Still Pond Station Park, both of which are ideal for eco-friendly, family vacations. Additionally, the CopperPlex stadium caters to sports enthusiasts, making this area a versatile destination for outdoor and recreational activities.
  • Georgetown: Situated in the vicinity of Chestertown, Georgetown offers a delightful blend of outdoor and romantic experiences. Visitors can explore the picturesque Rock Hall Harbor, perfect for enjoying the beach scenery. The area also features the Chesapeake Bay Bridge, a modern architectural highlight. With access to local wineries, Georgetown is a charming spot for those looking to combine entertainment with relaxation.
  • Tolchester Beach: This village, also close to Chestertown, is perfect for those who love the beach and outdoor activities. Tolchester Beach is known for its family-friendly beach options and scenic views. Key attractions include the stunning Sandy Point State Park, known for its outdoor adventures, and the nearby Rock Hall Harbor for scenic beach experiences. This area is ideal for enjoying the summer months when the beach is in full swing.

10 tips to save on your car rental in and around Chestertown

  1. Use filters to find the right car: Refine your search by selecting vehicle type and specific features. Whether you need an SUV for extra room, a convertible for summer fun, or an economical car for budget-friendly travel, utilize the filters on Expedia to identify the best option for your journey.
  2. Book in advance to help lower costs: Rental rates can vary based on demand, so it’s wise to reserve your vehicle well ahead of your trip. Booking early typically secures lower prices and improves availability, especially during peak travel seasons.
  3. Consider a smaller car for savings: Smaller vehicles are usually less expensive to rent and easier to park in crowded areas. Mid-size rentals offer a nice compromise between cost, comfort, and fuel efficiency.
  4. Age guidelines: Drivers under 30 may encounter higher deposits or daily fees, and certain vehicle types—such as SUVs or luxury models—might be unavailable. This can also apply to renters over 70. Always verify age requirements prior to booking.
  5. Check fuel policies: Some rental agreements require a full-to-full fuel policy, which means you must return the car with a full tank to avoid additional charges. This is typically the most favorable option. Other policies may include full-to-empty or prepaid fueling options, which are acceptable as well; just remember to return the car empty in that scenario.
  6. Save on city and airport pickups: You may incur a surcharge for picking up your rental car at airports, but it can be worth the added convenience.
  7. Know your payment options: Many car rental companies only accept credit cards for payment.
  8. Understand your insurance coverage: Car rental insurance can help you avoid unnecessary expenses and provides peace of mind in case of unexpected incidents during your trip. It’s easy to add car rental insurance when booking through Expedia.
  9. Consider unlimited mileage: If you plan on taking long road trips, look for rental options that offer unlimited mileage to steer clear of extra fees.
  10. Bring your driver's license and ID: A valid driver's license is required to rent a car.

Best time to rent a car in and around Chestertown

The best value period to rent a car in and around Chestertown is May, when prices are at their lowest and demand is moderately high. April is also a good choice, with moderately low prices and average demand. June through August see higher demand and average prices, making it a busier time for rentals. November stands out as the most expensive month, despite having moderately low demand, while December also tends to be pricier with higher demand levels.

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 $62.

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 2026

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

Car Rental Information

Popular car types
SUV, Full Size, Economy
Car suppliers available
Our best deal of the day
$62
Our second best deal of the day
$64
Our third best deal of the day
$72
From the airport to your hotel
Airport Transportation
From popular domestic and international airports
Airport Car Rentals

Frequently asked questions

How much is a rental car per day in Chestertown?
Daily rental prices were as low as $62 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 $62 and $64. 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.

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