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Cheap Apartments for Rent in Chestertown, MD from $500 (13 Rentals)
Search the lowest-cost Apartments available for rent right now in Chestertown.
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$668 - $1,6751 to 2 Bedroom Apartments Contact Us For Availability
Perryman Station Senior Apartments, 62+
1222 Perryman RdAberdeen, MD 21001
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$765 - $1,3591 to 3 Bedroom Apartments Available Now
Windsor Valley Apartments
525 Meadowood DrEdgewood, MD 21040
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$777 - $1,231Studio to 2 Bedroom Apartments Available Now
Hartland Village Apartments
1103 Country Terrace RdEssex, MD 21221
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$938 - $1,584Studio 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
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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$1,004 - $1,4031 to 2 Bedroom Apartments Available Now
Kings Mill Apartments and Townhomes
1460 Hadwick DrEssex, MD 21221
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$1,045 - $1,2601 to 2 Bedroom Apartments Available Now
Edgewood Park Apartments
611 Edgewood RdEdgewood, MD 21040
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1 to 2 Bedroom Apartments
The Village at Slippery Hill Senior Apartments- 62+
320 Fallen Horse CirQueenstown, MD 21658
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.
6206 Baker Cir
EdgewoodMD21040
Showing Results 1-13, 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 an apartment in Chestertown?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Chestertown Studio Apartments | $1,331 | $777 | $1,650 |
| Chestertown 1 Bedroom Apartments | $1,548 | $668 | $2,539 |
| Chestertown 2 Bedroom Apartments | $1,766 | $950 | $2,900 |
| Chestertown 3 Bedroom Apartments | $1,927 | $1,050 | $3,200 |
| Chestertown 4 Bedroom Apartments | $2,285 | $1,989 | $2,400 |
Browse Top Apartments in Chestertown
See all Apartments in ChestertownExplore Chestertown
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 |
| Kings Mill Apartments and Townhomes | One bedroom Apartment | 1BR,1BA | $1,004 |
| Hyde Park Apartments | One Bedroom One Bath | 1BR,1BA | $1,007 |
Best Value Apartments for Rent in Chestertown, MD and Nearby
As of December 11, 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 | $1.36 |
| 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.
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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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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 $765 at Windsor Valley 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 $950 at Windsor Valley Apartments.
What is the most affordable Chestertown Three Bedroom Apartment?
The best deal on a cheap Chestertown Three Bedroom Apartment rental is at Windsor Valley Apartments and starts from $1,050.
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.