28 Tanager Rd
Kiryas JoelNY10950
Cheap Homes for Rent in Chester, NY from $1,800 (18 Rentals)
Search the lowest-cost Homes available for rent right now in Chester.
105 Sarah Wells Trail
Camp Bell HallNY10916
20 N Main St
MonroeNY10950
49 Tanager Rd
MonroeNY10950
15 Green Meadows Way
ChesterNY10918
66 Spring St
GoshenNY10924
122 Green Meadows Way
ChesterNY10918
85 E Main St
WashingtonvilleNY10992
2458 NY-302
MiddletownNY10941
37 Tanager Rd
MonroeNY10950
42 Tanager Rd
MonroeNY10950
5 Lexington Hills Rd
HarrimanNY10926
258 Phillipsburg Rd
MiddletownNY10940
5 Eagles Nest Dr
VernonNJ07462
125 Forest Ave
MonroeNY10950
95 Glenmere Homesites Rd
FloridaNY10921
3312 Whispering Hills Dr
ChesterNY10918
5 Owens Farm Rd
HighlandsNY10922
Showing Results 1-18, 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 | $2,366 | $1,800 | $2,800 |
| Chester 3 Bedroom Homes for Rent | $2,984 | $2,100 | $4,400 |
| Chester 4 Bedroom Homes for Rent | $3,375 | $2,500 | $3,800 |
| Chester 6 Bedroom Homes for Rent | $5,000 | $5,000 | $5,000 |
Browse Top Homes for Rent in Chester
Explore Chester
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. Knox Village in the Grove at New Windsor neighborhood has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,555. 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 |
| Knox Village | 1 Bedroom | 1BR,1BA | $1,555 |
| Rockwood Gardens Apartments | 1 Bed, 1 bath | 1BR,1BA | $1,580 |
| Sutton Hill Apartments | Sutton Hill Type 2 | 1BR,1BA | $1,670 |
| Idlewild Creek Apartments | 1 Bedroom 1 Bathroom | 1BR,1BA | $1,671 |
Best Value Apartments for Rent in Chester, NY
As of March 25, 2025 the best value apartment in the Chester area is the $2.00 price per square foot 1BR/Den/1.5BA Model at The Regency Club in the in the Downtown Middletown neighborhood starting from $2,300. The second greatest value Chester apartment is the Hampton Model at Sterling Parc at Middletown starting at $2,399 with a $2.13 price per square foot in the Downtown Middletown 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 Regency Club | 1BR/Den/1.5BA | 1BR,1.5BA | $2.00 |
| Sterling Parc at Middletown | Hampton | 2BR,2BA | $2.13 |
| Sherwood Forest Garden Apartments | 2x1 | 2BR,1BA | $1.98 |
| The Park At Main | C | 2BR,2BA | $2.25 |
| Golf Links Apartments | 1 Bed, 1.5 baths | 1BR,1.5BA | $2.09 |
| Woodbury Gardens | 2 Beds, 1 bath | 2BR,1BA | $2.28 |
| Carriage Hill Apartments | 1BR/ 1BA Deluxe | 1BR,1BA | $2.24 |
| Kensington Manor | New Construction | 1BR,1BA | $2.18 |
| 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 51 Apartments for Rent in Chester, NY with pricing that ranges from $594 to $4,505. There are also 40 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chester ranging from $1,800 to $5,000.
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 $1,800 to $5,000 with an average monthly rent of $3,140.
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.
Understanding Amenity Fees: Know Where You Might Be Able to Save Money
Written by: Amber Kanuckel
With the rising costs of housing, a lot of renters are asking this question: Is it possible to opt out of various amenities that your rental property offers so that you can avoid paying the fees.
Renting Smart: Lease Basics Every Renter Needs
Written by: Christine Leonard, Esq.
Often, in the excitement of finding a new place to live, there’s a rush to make it happen, and - too often - a new tenant signs a lease without reading it carefully.
Battling the Butts: Your Guide to the Reality of Smoke-Free Renting
Written by: Andrea Lee Negroni, JD
While many apartment buildings are “no smoking” properties, it’s hard to know exactly how many. In 2017, the National Apartment Association reported more than half of rental properties had smoke free policies.
How Your Move-In Inspection Can Protect Your Security Deposit
Written by: Christine Leonard, Esq.
If you’re anything like most people, housing costs represent a huge chunk of your monthly budget. On top of that, moving can be both a stressful and expensive affair.