407 Adams St
AnnapolisMD21403
Cheap Homes for Rent in Chester, MD from $1,500 (7 Rentals)
Search the lowest-cost Homes available for rent right now in Chester.
410 Melvin Ave
GrasonvilleMD21638
2201 Main St
ChesterMD21619
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.
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$1,9502 Bedroom Apartments Available Jun 1
1540 Postal Rd, Unit 210
1540 Postal RdChester, MD 21619
920 Boucher Ave
AnnapolisMD21403
24362 Widgeon Pl
Saint MichaelsMD21663
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.
1322 Hazel Nut Ct
AnnapolisMD21409
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Chester, MD Local Guide
Smith Island Cake by Jane Thomas is licensed under CC BY 2.0
How much does it cost to rent a home in Chester?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Chester 2 Bedroom Homes for Rent | $2,546 | $1,950 | $3,450 |
| Chester 3 Bedroom Homes for Rent | $3,363 | $1,800 | $7,800 |
| Chester 4 Bedroom Homes for Rent | $4,992 | $3,200 | $10,000+ |
| Chester 5 Bedroom Homes for Rent | $16,950 | $8,900 | $10,000+ |
Browse Top Homes for Rent in Chester
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Chester, MD Local Guide
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Cheapest Available Chester Apartments for Rent and Nearby
The cheapest available apartment rental in Chester, MD is a 1 Bed unit found at The Village at Slippery Hill Senior Apartments- 62+ priced from $975. The Villages at Marley Station Apartments in the Sloop Cove Landing neighborhood has the second lowest priced unit, which is a Studio apartment currently listed from $1,091. Here is today’s list of the most affordable Chester apartments for rent:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| The Village at Slippery Hill Senior Apartments- 62+ | A3 - One Bedroom | 1BR,1BA | $975 |
| The Villages at Marley Station Apartments | S1 | Studio,1BA | $1,091 |
| Obery Court | One Bedroom | 1BR,1BA | $1,277 |
Best Value Apartments for Rent in Chester, MD and Nearby
As of May 08, 2026 the best value apartment in the Chester area is the $1.71 price per square foot 2 Bed 2 Bath Model at Riva Trace Community of Annapolis in the in the Monticello neighborhood starting from $2,200. The second greatest value Chester apartment is the Teaberry Model at The Ashberry starting at $2,456 with a $2.29 price per square foot in the Sloop Cove Landing neighborhood. Here is today’s list of the best values for Chester apartments based on price per square foot:
| Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| Riva Trace Community of Annapolis | 2 Bed 2 Bath | 2BR,2BA | $1.71 |
| The Ashberry | Teaberry | 2BR,2BA | $2.29 |
| Annapolis Roads Apartments | 2BR 2BA | 2BR,2BA | $2.02 |
| Spa Cove Apartments | Chesapeake | 2BR,1BA | $2.01 |
| Obery Court | One Bedroom | 1BR,1BA | $1.64 |
| The Promenade at Easton | The Chester | 1BR,1BA | $2.14 |
| Americana Southdale | 1 Bedroom | 1BR,1BA | $2.36 |
| The Village at Slippery Hill Senior Apartments- 62+ | A5 - One Bedroom | 1BR,1BA | $1.69 |
| Quiet Waters Landing | A1-1BD/1BA | 1BR,1BA | $2.31 |
| Beacon Pointe Apartments and Townhomes | A1-1BD/1BA | 1BR,1BA | $2.20 |
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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Explore Chester, MD Rentals by Map
See the most popular apartments and homes in Chester, MD
Frequently Asked Questions about Chester
What type of rentals are currently available in Chester?
There are currently 56 Apartments for Rent in Chester, MD with pricing that ranges from $1,129 to $4,269. There are also 41 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chester ranging from $1,595 to $25,000.
What is the current price range for Rental Homes in Chester?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Chester ranges from $1,595 to $25,000 with an average monthly rent of $5,969.
How much are larger Three and Four Bedroom Rentals in Chester?
For those who are looking for larger living arrangements, Three Bedroom Apartments in Chester range from $1,700 to $3,235, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,800 to $7,800. Four Bedroom Single-Family rentals are also available starting from $3,200 and Four Bedroom Apartments start at $2,995.
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
A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back
Written by: Lauren Harrington
I’m going to talk with you as a seasoned property manager and friend. So, let’s start with your security deposit. I want you to think about this guide as insider information. You deserve your deposit back.
Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts
Written by: Lauren Harrington
This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.
What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Written by: Lauren Harrington
This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.
Maximizing Your Refund: Essential Tax Tips for Renters
Written by: Christine Leonard, Esq.
Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.