107 South Dr
AberdeenMD21001
Cheap Homes for Rent in Chestertown, MD from $1,000 (14 Rentals)
Search the lowest-cost Homes available for rent right now in Chestertown.
6202 Cedar Dr
EdgewoodMD21040
23571 Lovely Ln
ChestertownMD21620
903 Woodbridge Ct
EdgewoodMD21040
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.
1861 Sudlersville Rd
ClaytonDE19938
1930 Eloise Ln
EdgewoodMD21040
21217 Texas Ave
ChestertownMD21620
1827 Grempler Way
EdgewoodMD21040
1331 Acorn Ridge Ct
EdgewoodMD21040
1741 Judy Way
EdgewoodMD21040
2005 Magnolia Woods Ct
EdgewoodMD21040
1302 Arabis Ct
BelcampMD21017
613 Red Lion Branch Rd
MillingtonMD21651
The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.
1325 E Spring Meadow Ct
EdgewoodMD21040
Showing Results 1-14, Page 1 of 1
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 | $1,937 | $1,095 | $4,300 |
| Chestertown 3 Bedroom Homes for Rent | $2,224 | $1,595 | $3,600 |
| Chestertown 4 Bedroom Homes for Rent | $2,921 | $2,150 | $4,000 |
Browse Top Homes for Rent in Chestertown
Explore Chestertown
Chestertown, MD Local Guide
- Chestertown Neighborhoods
- Nearby Cities
- ZIP codes
- Local Counties
Cheapest Neighborhoods for Apartments in Chestertown, MD
Pricing Updated: 08/20/2025Current 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 | $2,100 | $2,000 | 2 |
Cheapest Available Chestertown Apartments for Rent and Nearby
The cheapest available apartment rental in Chestertown, MD is a 3 Beds unit found at The Village at Slippery Hill II priced from $799. Hartland Village Apartments in the Hopewell Point neighborhood has the second lowest priced unit, which is a Studio apartment currently listed from $899. Here is today’s list of the most affordable Chestertown apartments for rent:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| The Village at Slippery Hill II | C2 - Three Bedroom Townhome | 3BR,2BA | $799 |
| Hartland Village Apartments | Studio | Studio,1BA | $899 |
| The Greens Apartments and Townhomes | Studio | Studio,1BA | $940 |
| Hyde Park Apartments | One Bedroom One Bath | 1BR,1BA | $999 |
| Essex Park Apartments and Townhomes | Two Bedroom Apartment | 2BR,1BA | $1,039 |
Best Value Apartments for Rent in Chestertown, MD and Nearby
As of August 20, 2025 the best value apartment in the Chestertown area is the $1.61 price per square foot 2 Bed 2 Bath w/ Den Model at Holly Oaks in the in the Holly Woods - Woodfield/Wyngate neighborhood starting from $2,050. The second greatest value Chestertown apartment is the Mingles 2 Bedroom Model at Kent Crossing Apartments starting at $1,675 with a $1.57 price per square foot in the Coventry Farms neighborhood. 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. |
|---|---|---|---|
| Holly Oaks | 2 Bed 2 Bath w/ Den | 2BR,2BA | $1.61 |
| Kent Crossing Apartments | Mingles 2 Bedroom | 2BR,2BA | $1.57 |
| The Willows at Cecilton | 2 BEDROOM | 2BR,1BA | $1.10 |
| Perkins Place | The Calvert | 2BR,1.5BA | $1.76 |
| Seven Oaks Townhomes | 2 Bedrooms 1.5 Bath | 2BR,1.5BA | $1.54 |
| Perryman Station Senior Apartments, 62+ | 2 bedroom | 2BR,2BA | $1.41 |
| Essex Park Apartments and Townhomes | Two Bedroom with Den Apartment | 2BR,1BA | $1.42 |
| Hyde Park Apartments | One Bedroom One Bath | 1BR,1BA | $1.45 |
| Seneca Bay Apartment Homes | One Bedroom - 629 sqft | 1BR,1BA | $1.49 |
| Kings Mill Apartments and Townhomes | One bedroom Apartment | 1BR,1BA | $1.66 |
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See the most popular apartments and homes in Chestertown, MD
Frequently Asked Questions about Chestertown
What type of rentals are currently available in Chestertown?
There are currently 56 Apartments for Rent in Chestertown, MD with pricing that ranges from $899 to $3,049. There are also 40 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestertown ranging from $1,005 to $4,300.
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 $1,005 to $4,300 with an average monthly rent of $2,071.
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 $3,049, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,595 to $3,600. Four Bedroom Single-Family rentals are also available starting from $2,150 and Four Bedroom Apartments start at $1,969.
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.
The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Written by: Christine Leonard, Esq.
Hard truth. Moving is never easy. I’ve done it all – from local moves to cross-country relocations From packing to unpacking the last box, I have found moving to be an exhausting, expensive and stressful experience every time.
Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Written by: Christine Leonard, Esq.
Throughout the day, think about all the times that you have to pay for something. So many of us reach automatically for a credit card or even our phone for a quick payment.
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
Written by: Cheryl Bowman
A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.
The Art of the Rental Viewing: What to look for during a property tour
Written by: Marie Brown
You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.