3102 Whispering Hills Dr
ChesterNY10918
Cheap Homes for Rent in Chester, NY from $1,500 (7 Rentals)
Search the lowest-cost Homes available for rent right now in Chester.
264 Reservoir Rd
GoshenNY10924
42 Woodland Cir S
MonroeNY10950
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
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9 Laurel Trail
MonroeNY10950
14 Bridge St
FloridaNY10921
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.
1358 Kings Hwy
ChesterNY10918
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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 | $2,315 | $1,750 | $2,800 |
| Chester 3 Bedroom Homes for Rent | $3,275 | $1,500 | $6,500 |
| Chester 4 Bedroom Homes for Rent | $4,917 | $2,250 | $8,000 |
| Chester 6 Bedroom Homes for Rent | $3,675 | $2,850 | $4,500 |
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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 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 | $1,625 |
Best Value Apartments for Rent in Chester, NY
As of June 10, 2025 the best value apartment in the Chester area is the $2.12 price per square foot 2BR/2BA Model at The Regency Club in the in the Downtown Middletown neighborhood starting from $2,500. 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 Regency Club | 2BR/2BA | 2BR,2BA | $2.12 |
| Woodbury Gardens | Two Bedroom | 2BR,2BA | $2.02 |
| The Park At Main | C | 2BR,2BA | $2.25 |
| Rockwood Gardens Apartments | 2 Beds, 1 bath | 2BR,1BA | $2.36 |
| Imperial Gardens Apartment Homes | Two Bedroom 1.5 Bath-916 sqft | 2BR,1.5BA | $2.36 |
| Kensington Manor | New Construction | 1BR,1BA | $2.18 |
| Summit Terrace Luxury Apartments | Rockland | 1BR,1BA | $2.30 |
| Crestwood Apartments | 2-Bedroom Large | 2BR,1BA | $2.45 |
| 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 $11,970. There are also 40 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chester ranging from $1,500 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 $1,500 to $8,000 with an average monthly rent of $3,296.
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 $2,600 to $3,026, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,500 to $6,500. Four Bedroom Single-Family rentals are also available starting from $2,250 and Four Bedroom Apartments start at $2,500.
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.
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.
The Freedom of Short-Term Leases: Exploring the Advantages for Renters
Written by: Bobbi Jackson
If you’re looking to relocate right now, a popular solution that may best fit your current rental needs is a short-term lease.
Navigating the Rental Market: Tips for First-Time Renters
Written by: Sandy Baker
Making the decision to rent is exciting and terrifying at the same time. For many people, there are a lot of unknowns.