6206 Baker Cir
EdgewoodMD21040
Cheap Homes for Rent in Chestertown, MD from $1,000 (6 Rentals)
Search the lowest-cost Homes available for rent right now in Chestertown.
6203 Edgewood Rd
EdgewoodMD21040
73 Cattail Ln
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.
118 N Water St
ChestertownMD21620
1730 Fountain Rock Way
EdgewoodMD21040
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.
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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 | $1,575 | $1,095 | $2,000 |
| Chestertown 3 Bedroom Homes for Rent | $2,189 | $1,195 | $3,800 |
| Chestertown 4 Bedroom Homes for Rent | $2,731 | $2,100 | $4,000 |
Browse Top Homes for Rent in Chestertown
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Chestertown, MD Local Guide
- Chestertown Neighborhoods
- Nearby Cities
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Cheapest Available Chestertown Apartments for Rent and Nearby
The cheapest available apartment rental in Chestertown, MD is a 1 Bed unit found at Windsor Valley Apartments in the Goose Pond Estates neighborhood priced from $765. 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 |
|---|---|---|---|
| Windsor Valley Apartments | Windsor III- 1 BR, 1 BA | 1BR,1BA | $765 |
| Hartland Village Apartments | Studio | Studio,1BA | $777 |
| The Greens Apartments and Townhomes | Studio | Studio,1BA | $940 |
Best Value Apartments for Rent in Chestertown, MD and Nearby
As of December 12, 2025 the best value apartment in the Chestertown area is the $1.00 price per square foot 3 Bedrooms 1 Bath Model at Foxridge Townhomes in the in the Hopewell Point neighborhood starting from $1,727. 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 | $1.00 |
| Winston's Choice Family Townhomes | UNIT A-INTERIOR UNIT | 3BR,2.5BA | $0.96 |
| Holly Oaks | 2 Bed 2 Bath | 2BR,2BA | $1.58 |
| Kingston Townhomes | 3 Bedrooms 1 Bath | 3BR,1BA | $1.43 |
| The Willows at Cecilton | 2 BEDROOM | 2BR,1BA | $1.10 |
| Seneca Bay Apartment Homes | Two Bedroom - 853 sqft | 2BR,1BA | $1.55 |
| Kings Mill Apartments and Townhomes | Two Bedroom Townhome | 2BR,1BA | $1.64 |
| Hyde Park Apartments | One Bedroom One Bath | 1BR,1BA | $1.38 |
| The Village at Slippery Hill Senior Apartments- 62+ | A5 - One Bedroom | 1BR,1BA | $1.69 |
| 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
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.
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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 54 Apartments for Rent in Chestertown, MD with pricing that ranges from $668 to $3,200. There are also 40 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestertown ranging from $1,095 to $4,000.
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 $4,000 with an average monthly rent of $2,165.
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 $3,200, 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 $2,100 and Four Bedroom Apartments start at $1,989.
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
Renting with Roommates: Realistic Expectations for Shared Lease
Written by: Christine Leonard, Esq.
Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.
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.