7 Goldman Rd
MonroeNY10950
Cheap Homes for Rent in Chester, NY from $1,400 (8 Rentals)
Search the lowest-cost Homes available for rent right now in Chester.
55 Walton Terrace
MonroeNY10950
5 Goldman Rd
MonroeNY10950
20 Peddler Hill Rd
Blooming GroveNY10914
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.
24 Cromwell Hill Rd
MonroeNY10950
39 Tanager Rd
MonroeNY10950
239 W Main St
GoshenNY10924
30 Tanager Rd
Kiryas JoelNY10950
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.
Showing Results 1-8, Page 1 of 1
Chester, NY Local Guide
Checkers by darronb 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 | $2,075 | $1,400 | $2,750 |
| Chester 3 Bedroom Homes for Rent | $3,063 | $2,700 | $3,850 |
| Chester 4 Bedroom Homes for Rent | $4,568 | $2,500 | $6,750 |
| Chester 5 Bedroom Homes for Rent | $3,400 | $3,400 | $3,400 |
| Chester 7 Bedroom Homes for Rent | $3,900 | $3,900 | $3,900 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Top Homes for Rent in Chester
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Chester, NY Local Guide
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Cheapest Available Chester Apartments for Rent and Nearby
The cheapest available apartment rental in Chester, NY is a 1 Bed unit found at Liberty Green Apartments priced from $495. Devon Woods has the second lowest priced unit, which is a 1 Bed apartment currently listed from $914. Here is today’s list of the most affordable Chester apartments for rent:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Liberty Green Apartments | LG1 | 1BR,1BA | $495 |
| Devon Woods | 2nd Fl 1br | 1BR,1BA | $914 |
| Hearthstone Apartments | 1 Bed / 1 Bath - 50% | 1BR,1BA | $1,075 |
Best Value Apartments for Rent in Chester, NY and Nearby
As of April 16, 2026 the best value apartment in the Chester area is the $2.15 price per square foot B - 2B3 2nd Floor Model at Southgate Middletown in the in the Middletown Goshen neighborhood starting from $2,800. The second greatest value Chester apartment is the 1BR/Den/1.5BA Model at The Regency Club starting at $2,400 with a $2.09 price per square foot in the Presidential Heights 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. |
|---|---|---|---|
| Southgate Middletown | B - 2B3 2nd Floor | 2BR,2BA | $2.15 |
| The Regency Club | 1BR/Den/1.5BA | 1BR,1.5BA | $2.09 |
| Kensington Manor | New Construction | 1BR,1BA | $2.30 |
| Woodbury Gardens | One Bedroom | 1BR,1BA | $2.11 |
| Hawkins Apartments | 1 Bed, 1 bath | 1BR,1BA | $2.26 |
| Knox Village | 1 Bedroom | 1BR,1BA | $2.05 |
| Crestwood Apartments | 1-Bedroom | 1BR,1BA | $2.30 |
| Liberty Green Apartments | LG1 | 1BR,1BA | $0.68 |
| Devon Woods | 1st Fl 1br | 1BR,1BA | $1.47 |
| Hearthstone Apartments | 1 Bed / 1 Bath - 60% | 1BR,1BA | $1.98 |
10 Hidden Costs of Renting You Should Budget for Before Signing a Lease
Avoid financial stress when renting. Learn about the 10 most common hidden costs—from pet fees to utilities—you must budget for before you sign a lease.
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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.
Read ArticleCash 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.
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.
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See the most popular apartments and homes in Chester, NY
Frequently Asked Questions about Chester
What type of rentals are currently available in Chester?
There are currently 61 Apartments for Rent in Chester, NY with pricing that ranges from $495 to $3,423. There are also 35 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chester ranging from $1,400 to $6,750.
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 $1,400 to $6,750 with an average monthly rent of $3,150.
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
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.
18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Written by: Lauren Harrington
Renting your next home can feel thrilling and overwhelming at the same time.
A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment
Written by: Bob Mallory
Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.