
Luxury Apartments for Rent in Chester, NY with Swimming Pool (37 Rentals)
The most luxurious Apartments in Chester with high-end amenities, features, and finishes.


3312 Whispering Hills Dr

1507 Whispering Hills Dr

3411 Whispering Hills Dr

3011 Whispering Hills Dr

14 Lake View Dr

Residences at West Hills Country Club

Southgate Middletown

Sutton Hill Apartments

Sterling Parc at Middletown

Imperial Gardens Apartment Homes

Boulder Pointe Apartments

Lamplight Village Apartments

The Regency Club

Idlewild Creek Apartments

The Point at Sutton Hill

Kensington Manor

36 4 Corners Rd

95 Glenmere Homesites Rd

4 Golf Dr

63 Butler Dr

143 Montgomery St

51 Wedgewood Dr

2 Quail Ln

146 S Church St

24 Northgate

125 Forest Ave

32 Claire Dr

8 Lake Ave

425 Old Dutch Hollow Rd

46 Midway Dr

54 Peddler Hill Rd

57 School Rd

16 Hawxhurst Rd

11 Peter Bush Dr

5 Friendly Acres

5 Owens Farm Rd
Chester, NY Local Guide

How much does it cost to rent an apartment in Chester?
Bedroom | Average Rent | Cheapest Rent | Highest Rent |
---|---|---|---|
Chester Studio Apartments | $1,859 | $1,450 | $3,350 |
Chester 1 Bedroom Apartments | $1,970 | $594 | $3,825 |
Chester 2 Bedroom Apartments | $2,418 | $698 | $4,505 |
Chester 3 Bedroom Apartments | $2,927 | $2,585 | $4,455 |
Explore Chester
Chester, NY Local Guide
- Nearby Cities
- ZIP codes
- Local Counties
- School Districts
Quick Rent Budget Calculator
How much rent can you afford?
The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.
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 Chester Apartments with Swimming Pool
What is the Cheapest Swimming Pool apartment in Chester?
Currently the most affordable Apartment in Chester with Swimming Pool is at Crestwood Apartments listed at $1,450.
How much is the average rent for Chester Apartments with Swimming Pool?
The average rent for a Apartment in Chester with Swimming Pool is $2,365.
What is the largest Chester Apartment for rent with Swimming Pool?
Today's Apartment with Swimming Pool and the most square footage in Chester is a 2,100 square feet unit starting from $1,695 at Kensington Manor.
What is the average size for Chester Apartments for rent with Swimming Pool?
The average size for a rental with Swimming Pool in Chester is currently at 760 sq ft.
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.

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.

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.

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.

Signing Your Apartment Lease: The Basics
Written by: Trey Huguley
When you're about to sign a lease for the first time, it can feel a bit overwhelming. You don’t want to miss any important details hidden in the fine print.