Cheap Apartments for Rent in Chestertown, MD from $500 (15 Rentals)

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Search the lowest-cost Apartments available for rent right now in Chestertown.

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Chestertown, MD Local Guide

Cheapest Neighborhoods for Apartments in Chestertown, MD

Pricing Updated: 03/23/2025

Current apartment rentals in the Chestertown, MD area range in price from to with an overall median price of . Here is today’s list neighborhoods with the lowest median pricing for Chestertown Apartments for rent:

NeighborhoodMedian PriceMin PriceAvailable Units
Coventry Farms$1,900$1,000135

Cheapest Available Chestertown Apartments for Rent and Nearby

 

The cheapest available apartment rental in Chestertown, MD is a 1 Bed unit found at Center Park Apartments in the North Brook neighborhood priced from $770. The Village at Slippery Hill II has the second lowest priced unit, which is a 3 Beds apartment currently listed from $799. Here is today’s list of the most affordable Chestertown apartments for rent:

Apartment ListingModel NameBed/BathPriced From
Center Park Apartments1 Bed, 1 bath1BR,1BA$770
The Village at Slippery Hill IIC2 - Three Bedroom Townhome3BR,2BA$799
Hartland Village ApartmentsStudioStudio,1BA$875
The Greens Apartments and TownhomesStudioStudio,1BA$940
The Village at Slippery Hill Senior ApartmentsA5 - One Bedroom1BR,1BA$1,020

Best Value Apartments for Rent in Chestertown, MD and Nearby

As of March 23, 2025 the best value apartment in the Chestertown area is the $1.39 price per square foot Patriot Village - Freedom Model at Aberdeen Proving Ground on Post Housing in the in the Greenway Farm neighborhood starting from $1,995. The second greatest value Chestertown apartment is the C2 - Three Bedroom Townhome Model at The Village at Slippery Hill II starting at $799 with a $0.60 price per square foot . Here is today’s list of the best values for Chestertown apartments based on price per square foot:

Apartment ListingModel NameBed/BathPrice Per Sq.Ft.
Aberdeen Proving Ground on Post HousingPatriot Village - Freedom3BR,2.5BA$1.39
The Village at Slippery Hill IIC2 - Three Bedroom Townhome3BR,2.5BA$0.60
Harborside Village Apartments2 bedroom, 2 baths (D1, D2, G1, G2)2BR,2BA$1.42
Holly Circle Townhouses3 Bedroom 1 Bath Townhouses Ready to Lease!3BR,1BA$1.38
Winston's Choice Family TownhomesUNIT B3BR,2BA$1.15
Kingston Townhomes3 Bedrooms 1 Bath3BR,1BA$1.43
The Willows at Cecilton2 BEDROOM2BR,1BA$1.10
Brookside Station Apartments2 Bedroom 1 Bath2BR,1BA$1.04
Seven Oaks Townhomes2 Bedrooms 1.5 Bath2BR,1.5BA$1.42
Essex Park Apartments and TownhomesTwo Bedroom Townhome2BR,1BA$1.45

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Location, Location, Location!

Explore Chestertown, MD Rentals by Map

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See the most popular apartments and homes in Chestertown, MD

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Getting Around Chestertown, MD

Walk Score®

47 / 100

Car-Dependent

Most errands require a car

Bike Score®

55 / 100

Bikeable

Some bike infrastructure

What Are Walk Score®, Transit Score®, and Bike Score® Ratings?

  • Walk Score® measures the walkability of any address.
  • Transit Score® measures access to public transit.
  • Bike Score® measures the bikeability of any address.

Frequently Asked Questions about Cheap Chestertown Apartments

What is the Cheapest Studio apartment in Chestertown?

Currently the most affordable Cheap Studio Apartment in Chestertown is at Hartland Village Apartments listed at $875.

How much is rent for a Cheap One Bedroom Chestertown Apartment?

The lowest price for a Cheap One Bedroom Chestertown Apartment is $770 at Center Park Apartments.

What is the lowest price for a Cheap Two Bedroom Chestertown Apartment for rent?

Today's best deal for a Cheap Two Bedroom Apartment in Chestertown is starting from $1,039 at Essex Park Apartments and Townhomes.

What is the most affordable Chestertown Three Bedroom Apartment?

The best deal on a cheap Chestertown Three Bedroom Apartment rental is at The Village at Slippery Hill II and starts from $799.

Expert Rental Resources

Helpful Apartment Articles, How-To's and Tips

The rental experts at ApartmentHomeLiving.com provide you with top advice, tools, and tips for understanding the leasing process and finding the perfect rental. Here are a few helpful rental and leasing articles from our experts to guide you on your search.

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Understanding Amenity Fees: Know Where You Might Be Able to Save Money

Written by: Amber Kanuckel

With the rising costs of housing, a lot of renters are asking this question: Is it possible to opt out of various amenities that your rental property offers so that you can avoid paying the fees.

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What to Know About Fees and Fines When Renting

Written by: Trey Huguley

When it comes to renting a new apartment or home there can be a number of fees that you will want to keep in mind going into the process.

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Battling the Butts: Your Guide to the Reality of Smoke-Free Renting

Written by: Andrea Lee Negroni, JD

While many apartment buildings are “no smoking” properties, it’s hard to know exactly how many. In 2017, the National Apartment Association reported more than half of rental properties had smoke free policies.

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How Your Move-In Inspection Can Protect Your Security Deposit

Written by: Christine Leonard, Esq.

If you’re anything like most people, housing costs represent a huge chunk of your monthly budget. On top of that, moving can be both a stressful and expensive affair.