30 Peddler Hill Rd
Blooming GroveNY10950
Cheap Homes for Rent in Chester, NY from $1,800 (7 Rentals)
Search the lowest-cost Homes available for rent right now in Chester.
339 W Main St
GoshenNY10924
17 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.
235-237-237 Main St
CornwallNY12518
84 Carpenter Ave
NewburghNY12550
43 Tanager Rd
MonroeNY10950
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.
349 W Main St
GoshenNY10924
Showing Results 1-7, 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 | $2,425 | $2,000 | $3,000 |
| Chester 3 Bedroom Homes for Rent | $3,050 | $2,700 | $3,350 |
| Chester 4 Bedroom Homes for Rent | $4,237 | $2,950 | $8,500 |
| Chester 5 Bedroom Homes for Rent | $3,500 | $3,500 | $3,500 |
| Chester 6 Bedroom Homes for Rent | $3,400 | $3,400 | $3,400 |
Browse Top Homes for Rent in Chester
Explore Chester
Chester, NY Local Guide
- Nearby Cities
- ZIP codes
- Local Counties
- School Districts
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 |
| Crestwood Apartments | Studio | Studio,1BA | $1,450 |
Best Value Apartments for Rent in Chester, NY and Nearby
As of January 02, 2026 the best value apartment in the Chester area is the $2.28 price per square foot 2 bedroom 2nd floor Model at Harriman Woods Apartments in the in the Estates of Briarcliff neighborhood starting from $2,125. The second greatest value Chester apartment is the New Construction Model at Kensington Manor starting at $1,895 with a $2.18 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. |
|---|---|---|---|
| Harriman Woods Apartments | 2 bedroom 2nd floor | 2BR,1BA | $2.28 |
| Kensington Manor | New Construction | 1BR,1BA | $2.18 |
| Woodbury Gardens | One Bedroom | 1BR,1BA | $2.11 |
| Slatewood Apartments | 1 Bed | 1BR,1BA | $2.33 |
| Hawkins Apartments | 1 Bed, 1 bath | 1BR,1BA | $2.26 |
| Imperial Gardens Apartment Homes | One Bedroom-772 sqft | 1BR,1BA | $2.36 |
| Knox Village | 1 Bedroom | 1BR,1BA | $2.05 |
| Crestwood Apartments | 1-Bedroom | 1BR,1BA | $2.37 |
| Liberty Green Apartments | LG1 | 1BR,1BA | $0.68 |
| Devon Woods | 1st Fl 1br | 1BR,1BA | $1.47 |
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.
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.
Let everyone know!
Do you know the Chester area?
If you’re an expert on all things Chester, tell us what you love (and don't) by rating it and writing a review.
Write a Review
Remember the 3 Rules of Real Estate:Location, Location, Location!
Explore Chester, NY Rentals by Map
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 63 Apartments for Rent in Chester, NY with pricing that ranges from $495 to $8,970. There are also 36 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chester ranging from $1,800 to $8,500.
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 $1,800 to $8,500 with an average monthly rent of $3,082.
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 $1,411 to $4,675, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,700 to $3,350. Four Bedroom Single-Family rentals are also available starting from $2,950 and Four Bedroom Apartments start at $8,471.
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
How to Make Your Apartment Holiday-Ready: Renter-Friendly Tips
Written by: Justin Habersaat
Getting your apartment ready for the holidays can be exciting but sometimes challenging in a smaller space. Here are some modern tips to keep things festive, safe, and inviting this season.
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!