6202 Cedar Dr
EdgewoodMD21040
Cheap Homes for Rent in Chestertown, MD from $1,000 (8 Rentals)
Search the lowest-cost Homes available for rent right now in Chestertown.
6203 Edgewood Rd
EdgewoodMD21040
105 S Lynchburg St
ChestertownMD21620
1537 Mitchell Ln
AberdeenMD21001
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.
1857 Simons Ct
EdgewoodMD21040
1827 Grempler Way
EdgewoodMD21040
1741 Judy Way
EdgewoodMD21040
845 W Spring Meadow Ct
EdgewoodMD21040
The Art of the Rental Viewing: What to look for during a property tour
Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.
Showing Results 1-8, 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 | $2,363 | $1,095 | $4,300 |
| Chestertown 3 Bedroom Homes for Rent | $2,188 | $1,195 | $3,500 |
| Chestertown 4 Bedroom Homes for Rent | $2,785 | $1,850 | $3,200 |
| Chestertown 5 Bedroom Homes for Rent | $2,200 | $2,100 | $2,300 |
Browse Top Homes for Rent in Chestertown
Explore Chestertown
Chestertown, MD Local Guide
- Chestertown Neighborhoods
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Cheapest Neighborhoods for Apartments in Chestertown, MD
Pricing Updated: 06/20/2025Current 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 | $2,125 | $1,300 | 4 |
Cheapest Available Chestertown Apartments for Rent and Nearby
The cheapest available apartment rental in Chestertown, MD is a 1 Bed unit found at The Village at Slippery Hill II priced from $585. Hartland Village Apartments in the Hopewell Point neighborhood has the second lowest priced unit, which is a Studio apartment currently listed from $869. 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 | A1 - One Bedroom Apartment | 1BR,1BA | $585 |
| Hartland Village Apartments | Studio | Studio,1BA | $869 |
| The Greens Apartments and Townhomes | Studio | Studio,1BA | $940 |
Best Value Apartments for Rent in Chestertown, MD and Nearby
As of June 21, 2025 the best value apartment in the Chestertown area is the $0.93 price per square foot 3 Bedrooms 1 Bath Model at Foxridge Townhomes in the in the Hopewell Point neighborhood starting from $1,607. The second greatest value Chestertown apartment is the Patriot Village - Patriot Model at Aberdeen Proving Ground on Post Housing starting at $2,300 with a $1.39 price per square foot in the Greenway Farm 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. |
|---|---|---|---|
| Foxridge Townhomes | 3 Bedrooms 1 Bath | 3BR,1BA | $0.93 |
| Aberdeen Proving Ground on Post Housing | Patriot Village - Patriot | 4BR,2.5BA | $1.39 |
| Holly Circle Townhouses | 3 Bed 1.5 Bath | 3BR,1.5BA | $1.33 |
| Holly Oaks | 2 Bed 2 Bath | 2BR,2BA | $1.58 |
| Kingston Townhomes | 3 Bedrooms 1 Bath | 3BR,1BA | $1.42 |
| Carriage Court Apartments | 3 bedroom 2 bathrooms | 3BR,2BA | $1.27 |
| Kent Crossing Apartments | Mingles 2 Bedroom | 2BR,2BA | $1.57 |
| The Willows at Cecilton | 2 BEDROOM | 2BR,1BA | $1.10 |
| Seven Oaks Townhomes | 2 Bedrooms 1.5 Bath | 2BR,1.5BA | $1.53 |
| The Village at Slippery Hill II | A1 - One Bedroom Apartment | 1BR,1BA | $0.81 |
Quick Rent Budget Calculator
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Frequently Asked Questions about Chestertown
What type of rentals are currently available in Chestertown?
There are currently 53 Apartments for Rent in Chestertown, MD with pricing that ranges from $869 to $4,300. There are also 38 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestertown ranging from $1,095 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 $1,095 to $4,300 with an average monthly rent of $2,384.
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 $2,850, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,195 to $3,500. Four Bedroom Single-Family rentals are also available starting from $1,850 and Four Bedroom Apartments start at $1,929.
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.
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.
Know Your Budget: Calculating What You Can Realistically Afford When Renting
Written by: Lauren Harrington
Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.
The Freedom of Short-Term Leases: Exploring the Advantages for Renters
Written by: Bobbi Jackson
If you’re looking to relocate right now, a popular solution that may best fit your current rental needs is a short-term lease.