118 Green Meadows Way
ChesterNY10918
Cheap Homes for Rent in Chester, NY from $1,900 (10 Rentals)
Search the lowest-cost Homes available for rent right now in Chester.
30 Peddler Hill Rd
Blooming GroveNY10950
235-237-237 Main St
CornwallNY12518
84 Carpenter Ave
NewburghNY12550
9 Upper Hillman Rd
WarwickNY10990
2208 Whispering Hills Dr
ChesterNY10918
16 Jmd Dr
Kiryas JoelNY10950
10 Murray Ave
GoshenNY10924
1418 Whispering Hills Dr
ChesterNY10918
55 High St
MonroeNY10950
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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 | $2,635 | $2,000 | $3,000 |
| Chester 3 Bedroom Homes for Rent | $3,311 | $2,600 | $5,000 |
| Chester 4 Bedroom Homes for Rent | $3,930 | $3,000 | $6,000 |
| Chester 5 Bedroom Homes for Rent | $4,400 | $4,400 | $4,400 |
| Chester 6 Bedroom Homes for Rent | $5,500 | $5,500 | $5,500 |
| Chester 7 Bedroom Homes for Rent | $3,700 | $3,700 | $3,700 |
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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. Knox Village 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 | $1,625 |
Best Value Apartments for Rent in Chester, NY
As of November 14, 2025 the best value apartment in the Chester area is the $1.53 price per square foot 2 Bed 1 Bath Model at The 211 Luxury Lofts in the in the Downtown Middletown neighborhood starting from $2,300. The second greatest value Chester apartment is the Two Bedroom Model at Woodbury Gardens starting at $2,200 with a $2.02 price per square foot . 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 | 2 Bed 1 Bath | 2BR,1BA | $1.53 |
| Woodbury Gardens | Two Bedroom | 2BR,2BA | $2.02 |
| Boulder Pointe Apartments | 2 Bedrooms | 2 Bathrooms | 2BR,2BA | $2.28 |
| Rockwood Gardens Apartments | 2 Beds, 1 bath | 2BR,1BA | $2.36 |
| Kensington Manor | New Construction | 1BR,1BA | $2.18 |
| Loosestrife Fields | 1 Bedroom 1 bath | 1BR,1BA | $2.23 |
| Slatewood Apartments | 1 Bed | 1BR,1BA | $2.33 |
| Imperial Gardens Apartment Homes | One Bedroom-772 sqft | 1BR,1BA | $2.45 |
| Knox Village | 1 Bedroom | 1BR,1BA | $2.05 |
| Hawkins Apartments | 1 Bed, 1 bath | 1BR,1BA | $2.33 |
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Frequently Asked Questions about Chester
What type of rentals are currently available in Chester?
There are currently 60 Apartments for Rent in Chester, NY with pricing that ranges from $594 to $6,677. There are also 38 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chester ranging from $1,900 to $6,000.
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 $1,900 to $6,000 with an average monthly rent of $3,626.
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 $2,000 to $4,675, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,600 to $5,000. Four Bedroom Single-Family rentals are also available starting from $3,000 and Four Bedroom Apartments start at $6,677.
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.
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!
The Rental Move-In Inspection Checklist: A Guide for Renters
Written by: Trey Huguley
The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Written by: Christine Leonard, Esq.
For many people, obstacles can arise during the rental application process for a variety of issues.