26 Main St
ChesterNY10918
Cheap Apartments for Rent in Chester, NY from $500 (8 Rentals)
Search the lowest-cost Apartments available for rent right now in Chester.
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$594 - $1,5011 to 2 Bedroom Apartments Contact Us For Availability
Middlecrest Crossing 55+ Senior Apartments
76 Uhlig RdMiddletown, NY 10940
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$1,450 - $2,025Studio to 2 Bedroom Apartments Available Now
Crestwood Apartments
92 Fitzgerald DrMiddletown, NY 10940
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.
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Rent Specials
$1,525 - $2,250Studio to 2 Bedroom Apartments Available Now
Stevens Manor Apartments
644 Silver Lake Scotchtown RdMiddletown, NY 10941
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$1,555 - $2,4001 to 3 Bedroom Apartments Available Now
Knox Village
835 Blooming Grove TpkeNew Windsor, NY 12553
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1089 Pulaski Hwy
GoshenNY10924
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.
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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 an apartment in Chester?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Cheap Chester Studio Apartments | $1,710 | $1,450 | $1,900 |
| Cheap Chester 1 Bedroom Apartments | $1,973 | $594 | $3,522 |
| Cheap Chester 2 Bedroom Apartments | $2,366 | $698 | $4,221 |
| Cheap Chester 3 Bedroom Apartments | $2,811 | $2,450 | $3,465 |
| Cheap Chester 4 Bedroom Apartments | $8,500 | $8,500 | $8,500 |
Browse Top Apartments in Chester
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Chester, NY Local Guide
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Cheapest Available Chester Apartments for Rent
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
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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Getting Around Chester, NY
Walk Score®
29 / 100
Car-Dependent
Most errands require a car
Bike Score®
23 / 100
Somewhat Bikeable
Minimal 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 Chester Apartments
What is the Cheapest Studio apartment in Chester?
Currently the most affordable Cheap Studio Apartment in Chester is at Crestwood Apartments listed at $1,450.
How much is rent for a Cheap One Bedroom Chester Apartment?
The lowest price for a Cheap One Bedroom Chester Apartment is $1,555 at Knox Village.
What is the lowest price for a Cheap Two Bedroom Chester Apartment for rent?
Today's best deal for a Cheap Two Bedroom Apartment in Chester is starting from $1,810 at Knox Village.
What is the most affordable Chester Three Bedroom Apartment?
The best deal on a cheap Chester Three Bedroom Apartment rental is at Knox Village and starts from $2,200.
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.