
Luxury Apartments for Rent in Chester, NY with Swimming Pool (33 Rentals)
Higher End Luxurious Apartments in Chester.


3312 Whispering Hills Dr

2720 Whispering Hills Dr

3411 Whispering Hills Dr

Residences at West Hills Country Club

Southgate Middletown

Sutton Hill Apartments

Sterling Parc at Middletown

Imperial Gardens Apartment Homes

Boulder Pointe Apartments
It's time to soak up some sun!
One of the easiest and more obvious ways of enjoying the summer sun is to lounge out by your community pool. Learn a Few Rules to Keep in Mind while at the pool.

Lamplight Village Apartments

The Point at Sutton Hill

Idlewild Creek Apartments

Summit Terrace Luxury Apartments

The Regency Club

Kensington Manor

36 4 Corners Rd

63 Butler Dr

44 Scotchtown Ave

3 Shale Ln
Navigating the Rental Market: Tips for First-Time Renters
Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.

146 S Church St

48 Natalie Ct

46 Midway Dr

54 Peddler Hill Rd

16 Dorothy Dr

57 School Rd

65 Lois Ln

261 Prospect Rd

3 Fredrick Dr

16 Hawxhurst Rd
Know Your Rights - How Discrimination Laws Impact Landlords and Tenants
Read our practical guide to landlord and tenant rights. Understand protected classes, reasonable accommodations, and legal exceptions to prevent housing discrimination.

22 Barr Ln

19 Lexington Hills Rd

12 Lexington Hills 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 | $1,450 | $1,450 | $1,450 |
Chester 1 Bedroom Apartments | $2,044 | $594 | $4,140 |
Chester 2 Bedroom Apartments | $2,458 | $698 | $4,555 |
Chester 3 Bedroom Apartments | $2,734 | $2,585 | $3,026 |
Chester 4 Bedroom Apartments | $13,950 | $10,000 | $10,000+ |
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
How much is the average rent for Chester Apartments with Swimming Pool?
The average rent for a Apartment in Chester with Swimming Pool is $2,350.
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.
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.

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.

Rise of Digital Nomads: Remote Work Tips for Apartment Renters
Written by: Brandie Parton
As a digital nomad, you no longer call a set address or office building your home for eight hours of the day or more.

Know Your Rights - How Discrimination Laws Impact Landlords and Tenants
Written by: Christine Leonard, Esq.
Everyone needs a place to live and to call home. For decades, the federal government has established protections to ensure that individuals and families can find housing free from discriminatory barriers.

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.