820 Windstream Way
EdgewoodMD21040
Cheap Homes for Rent in Chestertown, MD from $1,200 (5 Rentals)
Search the lowest-cost Homes available for rent right now in Chestertown.
2244 Rd 185
HartlyDE19953
1704 Fountain Rock Way
EdgewoodMD21040
74 Swan St
AberdeenMD21001
4 Gladiolus Pl
Middle RiverMD21220
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Chestertown, MD Local Guide
High Street in w:Chestertown, Maryland by Jennifer Schmidt is licensed under Internal
How much does it cost to rent a home in Chestertown?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Chestertown 2 Bedroom Homes for Rent | $1,625 | $1,275 | $2,100 |
| Chestertown 3 Bedroom Homes for Rent | $2,248 | $1,600 | $3,500 |
| Chestertown 4 Bedroom Homes for Rent | $2,824 | $1,950 | $3,350 |
Browse Top Homes for Rent in Chestertown
Explore Chestertown
Chestertown, MD Local Guide
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Cheapest Neighborhoods for Apartments in Chestertown, MD
Pricing Updated: 03/25/2025Current 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 |
Best Value Apartments for Rent in Chestertown, MD and Nearby
As of March 25, 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 |
| Perkins Place | The Garrett | 2BR,1BA | $1.58 |
| The Willows at Cecilton | 2 BEDROOM | 2BR,1BA | $1.10 |
| Brookside Station Apartments | 2 Bedroom 1 Bath | 2BR,1BA | $1.04 |
| Seven Oaks Townhomes | 2 Bedrooms 1.5 Bath | 2BR,1.5BA | $1.42 |
| Essex Park Apartments and Townhomes | Two Bedroom Townhome | 2BR,1BA | $1.45 |
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Frequently Asked Questions about Chestertown
What type of rentals are currently available in Chestertown?
There are currently 51 Apartments for Rent in Chestertown, MD with pricing that ranges from $770 to $3,150. There are also 33 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestertown ranging from $1,275 to $3,500.
What is the current price range for Rental Homes in Chestertown?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Chestertown ranges from $1,275 to $3,500 with an average monthly rent of $2,232.
How much are larger Three and Four Bedroom Rentals in Chestertown?
For those who are looking for larger living arrangements, Three Bedroom Apartments in Chestertown range from $1,285 to $3,150, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,600 to $3,500. Four Bedroom Single-Family rentals are also available starting from $1,950 and Four Bedroom Apartments start at $1,899.
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.
Renting Smart: Lease Basics Every Renter Needs
Written by: Christine Leonard, Esq.
Often, in the excitement of finding a new place to live, there’s a rush to make it happen, and - too often - a new tenant signs a lease without reading it carefully.
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.