
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.


2720 Whispering Hills Dr

21 Murray Dr

3312 Whispering Hills Dr

3322 Whispering Hills Dr

Residences at West Hills Country Club

Southgate Middletown

Sterling Parc at Middletown

Imperial Gardens Apartment Homes
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.

Boulder Pointe Apartments

Lamplight Village Apartments

The Point at Sutton Hill

Idlewild Creek Apartments

Summit Terrace Luxury Apartments

The Regency Club

Kensington Manor

63 Butler Dr

44 Scotchtown Ave
Smart Renter's Guide: Calculating Affordable Rent & Housing Costs
Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

3 Shale Ln

1 John Dr

406 Arlin Rd

9 Willard Pl

46 Midway Dr

54 Peddler Hill Rd

16 Dorothy Dr

65 Lois Ln

261 Prospect Rd
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.

57 School Rd

16 Hawxhurst Rd

13 Old Quaker Hill Rd

16 Gillian Ct

7 Forestdale Ave

40 Felter Hill Rd

19 Lexington Hills Rd

12 Lexington Hills Rd

10 Paradise Ln
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.

56 Benjamin Meadow 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 | $1,387 | $875 | $1,800 |
Chester 1 Bedroom Apartments | $2,079 | $594 | $3,805 |
Chester 2 Bedroom Apartments | $2,508 | $698 | $4,910 |
Chester 3 Bedroom Apartments | $2,781 | $2,600 | $3,026 |
Chester 4 Bedroom Apartments | $13,970 | $10,000 | $10,000+ |
Explore Chester
Chester, NY Local Guide
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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 $2,361.
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 776 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.

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.

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.