
Luxury Homes for Rent in Chester, NY (34 Rentals)
The most luxurious Homes in Chester with high-end amenities, features, and finishes.


1417 Whispering Hills Dr

14 Lori Ln

262 Reservoir Rd

17 Brookside Rd

508 Continental Dr
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.

9 Willard Pl

63 Butler Dr

707 Lenox Rd

317 Bellvale Lakes Rd

17 Highland Ave

46 Midway Dr

255 Prospect Rd

3 Country Club Dr

1290 Lakes

287 Seven Springs Mountain 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.

42 Merriewold Ln N

211 Prospect Rd

37 St Georges Ave

134 Quaker Hill Rd

7 Forestdale Ave

3 Gumwood Dr

125 N Main St

312 W Mombasha Rd

18 Briarwood Ave

146 S Church St

1 Pinehurst Cir

899 Lakes 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.

39 Paradise Valley Ln

373 Museum Village Rd

56 Benjamin Meadow Rd

11 Dorian Way

347 Museum Village Rd
Chester, NY Local Guide

How much does it cost to rent a home in Chester?
Bedroom | Average Rent | Cheapest Rent | Highest Rent |
---|---|---|---|
Chester 2 Bedroom Homes for Rent | $2,522 | $1,900 | $3,000 |
Chester 3 Bedroom Homes for Rent | $3,425 | $2,750 | $4,500 |
Chester 4 Bedroom Homes for Rent | $4,493 | $3,400 | $8,000 |
Chester 5 Bedroom Homes for Rent | $3,900 | $3,500 | $4,700 |
Chester 6 Bedroom Homes for Rent | $4,200 | $4,200 | $4,200 |
Browse Top Homes for Rent in Chester
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.
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 $8,500. There are also 40 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chester ranging from $1,600 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 $1,600 to $8,000 with an average monthly rent of $3,417.
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 $2,450 to $3,465, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,750 to $4,500. Four Bedroom Single-Family rentals are also available starting from $3,400 and Four Bedroom Apartments start at $8,500.
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.

Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Written by: Christine Leonard, Esq.
Throughout the day, think about all the times that you have to pay for something. So many of us reach automatically for a credit card or even our phone for a quick payment.

Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
Written by: Cheryl Bowman
A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.

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.