Cheap Apartments for Rent in Chestertown, MD from $500 (13 Rentals)
Search the lowest-cost Apartments available for rent right now in Chestertown.

Center Park Apartments

Hartland Village Apartments

The Greens Apartments and Townhomes

Essex Park Apartments and Townhomes

Brookside Station Apartments

The Village at Slippery Hill Senior Apartments

Seneca Bay Apartment Homes

Hopkins Point by OneWall

Merion Village, 62+ Living
Chestertown, MD Local Guide

How much does it cost to rent an apartment in Chestertown?
Bedroom | Average Rent | Cheapest Rent | Highest Rent |
---|---|---|---|
Chestertown Studio Apartments | $1,216 | $875 | $1,760 |
Chestertown 1 Bedroom Apartments | $1,531 | $770 | $2,244 |
Chestertown 2 Bedroom Apartments | $1,874 | $1,039 | $2,820 |
Chestertown 3 Bedroom Apartments | $1,957 | $1,285 | $2,799 |
Chestertown 4 Bedroom Apartments | $2,137 | $1,899 | $2,225 |
Browse Top Apartments in Chestertown
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Chestertown, MD Local Guide
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Cheapest Neighborhoods for Apartments in Chestertown, MD
Pricing Updated: 03/14/2025Current 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:
Neighborhood | Median Price | Min Price | Available Units |
---|---|---|---|
Coventry Farms | $1,900 | $1,000 | 135 |
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 Listing | Model Name | Bed/Bath | Priced From |
---|---|---|---|
Center Park Apartments | 1 Bed, 1 bath | 1BR,1BA | $770 |
The Village at Slippery Hill II | C2 - Three Bedroom Townhome | 3BR,2BA | $799 |
Hartland Village Apartments | Studio | Studio,1BA | $875 |
The Greens Apartments and Townhomes | Studio | Studio,1BA | $940 |
The Village at Slippery Hill Senior Apartments | A5 - One Bedroom | 1BR,1BA | $1,020 |
Best Value Apartments for Rent in Chestertown, MD and Nearby
As of March 14, 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 Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
---|---|---|---|
Aberdeen Proving Ground on Post Housing | Patriot Village - Freedom | 3BR,2.5BA | $1.39 |
The Village at Slippery Hill II | C2 - Three Bedroom Townhome | 3BR,2.5BA | $0.60 |
Harborside Village Apartments | 2 bedroom, 2 baths (D1, D2, G1, G2) | 2BR,2BA | $1.42 |
Holly Circle Townhouses | 3 Bedroom 1 Bath Townhouses Ready to Lease! | 3BR,1BA | $1.38 |
Winston's Choice Family Townhomes | UNIT B | 3BR,2BA | $1.15 |
Kingston Townhomes | 3 Bedrooms 1 Bath | 3BR,1BA | $1.43 |
The Willows at Cecilton | 2 BEDROOM | 2BR,1BA | $1.10 |
Brookside Station Apartments | 2 Bedroom 1 Bath | 2BR,1BA | $1.04 |
Essex Park Apartments and Townhomes | Two Bedroom Townhome | 2BR,1BA | $1.45 |
Seneca Bay Apartment Homes | One Bedroom - 629 sqft | 1BR,1BA | $1.56 |
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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.

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.

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.

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.

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.