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Cheap Apartments for Rent in Chestertown, MD from $500 (11 Rentals)
Search the lowest-cost Apartments available for rent right now in Chestertown.
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Rent Specials
$777 - $1,231Studio to 2 Bedroom Apartments Available Now
Hartland Village Apartments
1103 Country Terrace RdEssex, MD 21221
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$938 - $1,606Studio to 2 Bedroom Apartments Available Now
Hyde Park Apartments
1114 Tace DrEssex, MD 21221
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$940 - $1,365Studio to 2 Bedroom Apartments Available Now
The Greens Apartments and Townhomes
1207 Middleborough RdEssex, MD 21221
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$1,004 - $1,3251 to 2 Bedroom Apartments Available Now
Kings Mill Apartments and Townhomes
1460 Hadwick DrEssex, MD 21221
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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$1,045 - $1,2601 to 2 Bedroom Apartments Available Dec 1
Edgewood Park Apartments
611 Edgewood RdEdgewood, MD 21040
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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.
6202 Cedar Dr
EdgewoodMD21040
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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 an apartment in Chestertown?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Chestertown Studio Apartments | $1,290 | $899 | $1,701 |
| Chestertown 1 Bedroom Apartments | $1,504 | $1,004 | $2,278 |
| Chestertown 2 Bedroom Apartments | $1,765 | $1,140 | $3,039 |
| Chestertown 3 Bedroom Apartments | $1,974 | $1,339 | $2,900 |
| Chestertown 4 Bedroom Apartments | $2,267 | $1,919 | $2,400 |
Browse Top Apartments 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 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 |
| Hyde Park Apartments | One Bedroom One Bath | 1BR,1BA | $1,033 |
Best Value Apartments for Rent in Chestertown, MD and Nearby
As of October 25, 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.
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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.
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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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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
Getting Around Chestertown, MD
Walk Score®
47 / 100
Car-Dependent
Most errands require a car
Bike Score®
55 / 100
Bikeable
Some bike infrastructure
What Are Walk Score®, Transit Score®, and Bike Score® Ratings?
- Walk Score® measures the walkability of any address.
- Transit Score® measures access to public transit.
- Bike Score® measures the bikeability of any address.
Frequently Asked Questions about Cheap Chestertown Apartments
What is the Cheapest Studio apartment in Chestertown?
Currently the most affordable Cheap Studio Apartment in Chestertown is at Hartland Village Apartments listed at $777.
How much is rent for a Cheap One Bedroom Chestertown Apartment?
The lowest price for a Cheap One Bedroom Chestertown Apartment is $905 at Hartland Village Apartments.
What is the lowest price for a Cheap Two Bedroom Chestertown Apartment for rent?
Today's best deal for a Cheap Two Bedroom Apartment in Chestertown is starting from $699 at The Village at Slippery Hill II.
What is the most affordable Chestertown Three Bedroom Apartment?
The best deal on a cheap Chestertown Three Bedroom Apartment rental is at The Village at Slippery Hill II and starts from $799.
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.