108 Little Kidwell Ave
CentrevilleMD21617
Cheap Homes for Rent in Chestertown, MD from $1,000 (8 Rentals)
Search the lowest-cost Homes available for rent right now in Chestertown.
6209 Edgewood Rd
EdgewoodMD21040
6207 Edgewood Road C
6207 Edgewood Road Unit C
EdgewoodMD21040
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$1,2001 Bedroom Apartments Available Aug 15
24731 Langford Rd, Unit B
24731 Langford RdChestertown, MD 21620
What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Learn the official definition (spending 30% or more of your gross income on housing) and how to calculate your exact rent-to-income ratio. This guide offers expert tips on factoring in total housing costs (including utilities and fees) and budgeting accurately to avoid unnecessary financial strain.
722 Church Hill Rd
CentrevilleMD21617
80 Longbow Ln
HartlyDE19953
905 Swallow Crest Ct
EdgewoodMD21040
903 Woodbridge Ct
EdgewoodMD21040
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.
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Chestertown, MD Local Guide
How much does it cost to rent a home in Chestertown?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Chestertown 2 Bedroom Homes for Rent | $1,494 | $1,095 | $1,700 |
| Chestertown 3 Bedroom Homes for Rent | $2,157 | $1,195 | $2,700 |
| Chestertown 4 Bedroom Homes for Rent | $2,688 | $1,900 | $3,800 |
Browse Top Homes for Rent in Chestertown
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Chestertown, MD Local Guide
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Cheapest Neighborhoods for Apartments in Chestertown, MD
Pricing Updated: 06/14/2026Current 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 | $2,950 | $2,600 | 1 |
Cheapest Available Chestertown Apartments for Rent and Nearby
The cheapest available apartment rental in Chestertown, MD is a Studio unit found at The Greens Apartments and Townhomes in the Hopewell Point neighborhood priced from $687. Windsor Valley Apartments in the Goose Pond Estates neighborhood has the second lowest priced unit, which is a 1 Bed apartment currently listed from $765. Here is today’s list of the most affordable Chestertown apartments for rent:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| The Greens Apartments and Townhomes | Studio | Studio,1BA | $687 |
| Windsor Valley Apartments | Windsor III- 1 BR, 1 BA | 1BR,1BA | $765 |
| Kings Mill Apartments and Townhomes | One bedroom Apartment | 1BR,1BA | $785 |
Best Value Apartments for Rent in Chestertown, MD and Nearby
As of June 14, 2026 the best value apartment in the Chestertown area is the $1.10 price per square foot 3 bedroom 3 bathrooms Model at Carriage Court Apartments in the in the Trimble Meadows neighborhood starting from $1,600. The second greatest value Chestertown apartment is the 3 Bed 2 Bath Model at Holly Oaks starting at $2,225 with a $1.62 price per square foot in the Holly Woods - Woodfield/Wyngate 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. |
|---|---|---|---|
| Carriage Court Apartments | 3 bedroom 3 bathrooms | 3BR,2BA | $1.10 |
| Holly Oaks | 3 Bed 2 Bath | 3BR,2BA | $1.62 |
| Kingston Townhomes | 3 Bedrooms 1 Bath | 3BR,1BA | $1.53 |
| The Village at Slippery Hill Senior Apartments- 62+ | B1 - Two Bedroom | 2BR,1BA | $1.48 |
| Kings Mill Apartments and Townhomes | Two Bedroom Townhome | 2BR,1BA | $1.65 |
| Magnolia Farms | 2 Bedroom Apt | 2BR,1BA | $1.40 |
| 7019 Church Hill Rd, Unit B | 7019 Church Hill Rd | 2BR,1BA | $1.41 |
| Seneca Bay Apartment Homes | One Bedroom | 1BR,1BA | $1.40 |
| Hyde Park Apartments | Studio 1 Bathroom | Studio ,1BA | $1.60 |
| Windsor Valley Apartments | Windsor I & II- 1 BR, 1 BA | 1BR,1BA | $1.36 |
Don't Settle: How to Negotiate Your Apartment Lease and Save Money
Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.
Read Article
Real Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University
From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.
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How much rent can you afford?
The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.
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Pet Friendly Lifestyle
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Remember the 3 Rules of Real Estate:Location, Location, Location!
Explore Chestertown, MD Rentals by Map
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 60 Apartments for Rent in Chestertown, MD with pricing that ranges from $687 to $3,430. There are also 41 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestertown ranging from $1,030 to $3,800.
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 $1,030 to $3,800 with an average monthly rent of $1,888.
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 $1,050 to $3,430, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,195 to $2,700. Four Bedroom Single-Family rentals are also available starting from $1,900 and Four Bedroom Apartments start at $1,974.
Expert Rental Resources
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.
Articles, How-To's, and Tips
How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Written by: Robin Stewart
Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.
Pet-Friendly Renting: Everything You Need to Know Before You Move
Written by: Christine Leonard, Esq.
For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.
Creative Ways Developers Reimagine Retail Spaces as Residential Units
Written by: Robin Stewart
Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.
Neighborhood and Market Insights: How to Choose the Right Area to Rent
Written by: Robin Stewart
Apartment-hunting can be a gargantuan task. Renters have a wish list of items—some luxuries, some necessities—but finding what you seek in the right place is perhaps the most important part of the journey.