
Luxury Apartments for Rent in Chester, NY with Swimming Pool (35 Rentals)
The most luxurious Apartments in Chester with high-end amenities, features, and finishes.


1912 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

Summit Terrace Luxury Apartments

The Regency Club

Idlewild Creek Apartments

The Point at Sutton Hill

Kensington Manor

13 Lexington Hills Rd

1728 NY-17
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.

63 Butler Dr

1711 NY-17A

3 Shale Ln

146 S Church St

453 Clove Rd

9 Willard Pl

46 Midway Dr

9 Blythelea Rd
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.

1432 E Mombasha Rd

40 Felter Hill Rd

7 Forestdale Ave

5 Case Ct

1290 Lakes
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.

11 Dorian Way

126 Evan Rd

1535 NY-208

36 Weathervane Way

10 Paradise Ln

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 | $1,737 | $1,450 | $1,900 |
Chester 1 Bedroom Apartments | $2,066 | $594 | $3,585 |
Chester 2 Bedroom Apartments | $2,393 | $698 | $4,396 |
Chester 3 Bedroom Apartments | $2,802 | $2,600 | $3,026 |
Chester 4 Bedroom Apartments | $5,993 | $2,500 | $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 $2,337.
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 775 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.

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.