1089 Pulaski Hwy
GoshenNY10924
Cheap Homes for Rent in Chester, NY from $1,600 (5 Rentals)
Search the lowest-cost Homes available for rent right now in Chester.
44 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.
14 Bridge St
FloridaNY10921
19 Tanager Rd
MonroeNY10950
The Art of the Rental Viewing: What to look for during a property tour
Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.
5 Lexington Hills Rd
HarrimanNY10926
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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 | $2,522 | $1,900 | $3,000 |
| Chester 3 Bedroom Homes for Rent | $3,425 | $2,750 | $4,500 |
| Chester 4 Bedroom Homes for Rent | $4,493 | $3,400 | $8,000 |
| Chester 5 Bedroom Homes for Rent | $3,900 | $3,500 | $4,700 |
| Chester 6 Bedroom Homes for Rent | $4,200 | $4,200 | $4,200 |
Browse Top Homes for Rent in Chester
Explore Chester
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 Studio unit found at Crestwood Apartments in the Downtown Middletown neighborhood priced from $1,450. Stevens Manor Apartments in the Middletown Goshen neighborhood has the second lowest priced unit, which is a Studio apartment currently listed from $1,525. Here is today’s list of the most affordable Chester apartments for rent:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Crestwood Apartments | Studio | Studio,1BA | $1,450 |
| Stevens Manor Apartments | Studio | Studio,1BA | $1,525 |
| Knox Village | 1 Bedroom | 1BR,1BA | $1,555 |
Best Value Apartments for Rent in Chester, NY and Nearby
As of July 30, 2025 the best value apartment in the Chester area is the $1.63 price per square foot 3 Bed 1 Bath Model at The 211 Luxury Lofts in the in the Downtown Middletown neighborhood starting from $2,450. The second greatest value Chester apartment is the 1BR/Den/1.5BA Model at The Regency Club starting at $2,350 with a $2.05 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. |
|---|---|---|---|
| The 211 Luxury Lofts | 3 Bed 1 Bath | 3BR,1BA | $1.63 |
| The Regency Club | 1BR/Den/1.5BA | 1BR,1.5BA | $2.05 |
| Woodbury Gardens | Two Bedroom | 2BR,2BA | $2.02 |
| The Park At Main | C | 2BR,2BA | $2.25 |
| Idlewild Creek Apartments | 2 Bedroom 1 Bathroom | 2BR,1BA | $2.06 |
| Brookside Garden Apartments | 2 bedroom 1st floor | 2BR,1BA | $2.25 |
| Kensington Manor | New Construction | 1BR,1BA | $2.18 |
| Summit Terrace Luxury Apartments | Rockland | 1BR,1BA | $2.30 |
| Slatewood Apartments | 1 Bed | 1BR,1BA | $2.26 |
| Knox Village | 1 Bedroom | 1BR,1BA | $2.05 |
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Frequently Asked Questions about Chester
What type of rentals are currently available in Chester?
There are currently 56 Apartments for Rent in Chester, NY with pricing that ranges from $594 to $8,500. There are also 40 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chester ranging from $1,600 to $8,000.
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 $1,600 to $8,000 with an average monthly rent of $3,417.
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 $2,450 to $3,465, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,750 to $4,500. Four Bedroom Single-Family rentals are also available starting from $3,400 and Four Bedroom Apartments start at $8,500.
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.
Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Written by: Christine Leonard, Esq.
Throughout the day, think about all the times that you have to pay for something. So many of us reach automatically for a credit card or even our phone for a quick payment.
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
Written by: Cheryl Bowman
A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.
The Art of the Rental Viewing: What to look for during a property tour
Written by: Marie Brown
You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.
Know Your Budget: Calculating What You Can Realistically Afford When Renting
Written by: Lauren Harrington
Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.