108 Little Kidwell Ave
CentrevilleMD21617
Cheap Homes for Rent in Chestertown, MD from $1,000 (15 Rentals)
Search the lowest-cost Homes available for rent right now in Chestertown.
6202 Cedar Dr
EdgewoodMD21040
6203 Edgewood Rd
EdgewoodMD21040
32 Liberty St
AberdeenMD21001
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.
1861 Sudlersville Rd
ClaytonDE19938
2005 Magnolia Woods Ct
EdgewoodMD21040
7607 Bayside Ave
Sparrows PointMD21219
961 Angel Valley Ct N
EdgewoodMD21040
7828 Bodkin View Dr
PasadenaMD21122
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.
7480 Shortall St
ChestertownMD21620
2214 Redthorn Rd
Middle RiverMD21220
1315 E Spring Meadow Ct
EdgewoodMD21040
300 Oak St
CentrevilleMD21617
1315 SPRING Ct
EdgewoodMD21040
Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.
Showing Results 1-15, 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 | $1,761 | $1,095 | $2,300 |
| Chestertown 3 Bedroom Homes for Rent | $2,222 | $1,195 | $3,800 |
| Chestertown 4 Bedroom Homes for Rent | $2,488 | $2,000 | $3,100 |
| Chestertown 5 Bedroom Homes for Rent | $2,847 | $2,195 | $3,500 |
Browse Top Homes for Rent in Chestertown
Explore Chestertown
Chestertown, MD Local Guide
- Chestertown Neighborhoods
- Nearby Cities
- ZIP codes
- Local Counties
Cheapest Available Chestertown Apartments for Rent and Nearby
The cheapest available apartment rental in Chestertown, MD is a 2 Beds unit found at The Village at Slippery Hill II priced from $699. Hartland Village Apartments in the Hopewell Point neighborhood has the second lowest priced unit, which is a Studio apartment currently listed from $777. 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 | B1 - Two Bedroom Townhome | 2BR,1BA | $699 |
| Hartland Village Apartments | Studio | Studio,1BA | $777 |
| The Greens Apartments and Townhomes | Studio | Studio,1BA | $940 |
| Kings Mill Apartments and Townhomes | One bedroom Apartment | 1BR,1BA | $1,004 |
| Annhurst (MD) | Studio O | Studio,1BA | $1,110 |
Best Value Apartments for Rent in Chestertown, MD and Nearby
As of October 27, 2025 the best value apartment in the Chestertown area is the $0.96 price per square foot 3 Bedrooms 1 Bath Model at Foxridge Townhomes in the in the Hopewell Point neighborhood starting from $1,666. The second greatest value Chestertown apartment is the UNIT A-INTERIOR UNIT Model at Winston's Choice Family Townhomes starting at $1,339 with a $0.96 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 | $0.96 |
| Winston's Choice Family Townhomes | UNIT A-INTERIOR UNIT | 3BR,2.5BA | $0.96 |
| Kingston Townhomes | 3 Bedrooms 1 Bath | 3BR,1BA | $1.47 |
| The Willows at Cecilton | 2 BEDROOM | 2BR,1BA | $1.10 |
| Hyde Park Apartments | Two Bedroom One Bath | 2BR,1BA | $1.23 |
| The Village at Slippery Hill II | B3 - Two Bedroom Townhome | 2BR,1.5BA | $1.02 |
| Fox Run Apartments | 2 Bedroom 2 Bath | 2BR,2BA | $1.65 |
| The Village at Slippery Hill Senior Apartments | B1 - Two Bedroom | 2BR,1BA | $1.48 |
| Seneca Bay Apartment Homes | One Bedroom | 1BR,1BA | $1.63 |
| Kings Mill Apartments and Townhomes | One bedroom Apartment | 1BR,1BA | $1.57 |
Apartment Common Area Rules: What Renters Need to Know
From the lounge to the laundry room, understand your rights and responsibilities in shared apartment spaces. Get tips on pet rules, noise, and security.
Read Article
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 ArticleThe 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.
Read ArticleQuick Rent Budget Calculator
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.
Let everyone know!
Do you know the Chestertown area?
If you’re an expert on all things Chestertown, tell us what you love (and don't) by rating it and writing a review.
Write a Review
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 54 Apartments for Rent in Chestertown, MD with pricing that ranges from $899 to $3,200. There are also 47 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestertown ranging from $1,095 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 $1,095 to $3,800 with an average monthly rent of $2,329.
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 $1,339 to $3,200, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,195 to $3,800. Four Bedroom Single-Family rentals are also available starting from $2,000 and Four Bedroom Apartments start at $1,989.
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.
Apartment Common Area Rules: What Renters Need to Know
Written by: Christine Leonard, Esq.
Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.
How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!
The Rental Move-In Inspection Checklist: A Guide for Renters
Written by: Trey Huguley
The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Written by: Christine Leonard, Esq.
For many people, obstacles can arise during the rental application process for a variety of issues.