2 Bedroom Apartments for Rent in Chester, NY (53 Rentals)

How Many Bedrooms?Done
Select your price rangeDone
to
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Lifestyle Matching SearchDone
Learn more about Lifestyle Search
By AmenitiesDone
By Community TypeDone
Features and AvailabilityDone
Done
close
View Me
18 Main St
2 Bedroom Apartments

18 Main St

18 Main StChester, NY 10918
close
View Me
Green Meadows
2 Bedroom Apartments

Green Meadows

313 Green Meadows WayChester, NY 10918
close
View Me
78 High St
2 Bedroom Apartments

78 High St

78 High StChester, NY 10918
close
View Me
Meadow Hills
2 Bedroom Apartments

Meadow Hills

44 High StChester, NY 10918
  • Utilities Included

Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.

Read Article

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.

Read Article

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.

Read Article

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.

Read Article
close
View Me
29 N Main St
2 Bedroom Apartments

29 N Main St

29 N Main StFlorida, NY 10921
close
View Me
Knox Village
2 Bedroom Apartments

Knox Village

835 Blooming Grove TpkeNew Windsor, NY 12553
close
View Me
Crestwood Apartments
2 Bedroom Apartments

Crestwood Apartments

92 Fitzgerald DrMiddletown, NY 10940
  • Utilities Included
close
View Me
Golf Links Apartments
2 Bedroom Apartments

Golf Links Apartments

206 Golf Links RdMiddletown, NY 10940
  • Utilities Included
close
View Me
Kensington Manor
2 Bedroom Apartments

Kensington Manor

1 Kensington MnrMiddletown, NY 10941
  • Utilities Included
Showing Results 1-50, Page 1 of 2

Chester, NY Local Guide

Largest Available Chester 2 Bedroom Apartments

The largest available 2 Bedroom apartment unit in Chester, NY is found at Pulaski in the Glenview Hills At Florida neighborhood and is 1,350 square feet priced from $2,000. Southgate Middletown in the Middletown Goshen neighborhood has the second largest 2 Bedroom, which is sized at 1,302 square feet and currently listed start at $3,000. Here is today’s list of the largest available 2 Bedroom units in Chester:

Apartment ListingModel NameSquare FootagePriced From
Pulaski1,350 Sq Ft$2,000
Southgate MiddletownB-2B3 3rd Floor1,302 Sq Ft$3,000
Briarwood House Apartments2 BRM DUPLEX1,200 Sq Ft$2,940
The Regency Club2BR/2BA1,172 Sq Ft$2,550
Sterling Parc at MiddletownHampton1,125 Sq Ft$2,413
The Point at Sutton HillThe Point Type B1,111 Sq Ft$2,480
Woodbury GardensTwo Bedroom1,090 Sq Ft$2,200
Idlewild Creek Apartments2 Bedroom 1.5 Bathroom1,079 Sq Ft$2,153
Residences at West Hills Country Club2 Bedroom A1,078 Sq Ft$3,423
The Park At MainC1,076 Sq Ft$2,650

Cheapest Available Chester 2 Bedroom Apartments

As of May 03, 2026 the lowest priced 2 Bedroom apartment unit in Chester, NY is the 2 Bedroom Model starting from $1,810 at Knox Village . The second most affordable Chester 2 Bedroom is the Sutton Hill Type 4 Model at Sutton Hill Apartments starting at $1,850 in the Middletown Goshen neighborhood. The average price for all 2 Bedroom apartments in Chester is currently $2,325. Here is today’s list of the cheapest available 2 Bedroom options in Chester:

Apartment ListingModel NamePriced From
Knox Village2 Bedroom$1,810
Sutton Hill ApartmentsSutton Hill Type 4$1,850
Stoneridge Manor Apartments2 Beds, 2 baths$2,000
Imperial Gardens Apartment HomesTwo Bedroom-916 sqft$2,045
Woodbury GardensTwo Bedroom$2,100
Idlewild Creek Apartments2 Bedroom 1.5 Bathroom$2,153
Stevens Manor Apartments2BR/1.0BA$2,200
Country Manor Apartments2BR/1.5BA$2,200
Rockwood Gardens Apartments2 Beds, 1 bath$2,200
Carriage Hill Apartments2 BR$2,225

A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back

Learn the property manager's true secrets to a zero-deduction move-out. Use this step-by-step guide on documentation, cleaning, and lease-reading to reclaim your security deposit.

Read Article
Decorative image

10 Hidden Costs of Renting You Should Budget for Before Signing a Lease

Avoid financial stress when renting. Learn about the 10 most common hidden costs—from pet fees to utilities—you must budget for before you sign a lease.

Read Article
Decorative image

Don't Settle: How to Negotiate Your Apartment Lease and Save Money

Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.

Read Article
Decorative image

The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro

Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.

Read Article
Decorative image

Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting

Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.

Read Article
Decorative image

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.

decorative image of people with a giant lease agreement

Remember the 3 Rules of Real Estate:
Location, Location, Location!

Explore Chester, NY Rentals by Map

Decorative image of map

See the most popular apartments and homes in Chester, NY

View Map
Chester, NY Apartments Map
View Map
Chester, NY Rental Homes Map

Frequently Asked Questions about 2 Bedroom Chester Apartments

How much is the average rent for a 2 Bedroom Chester Apartment?

The average rent for a 2 Bedroom Apartment in Chester is $2,325.

What is the largest available 2 Bedroom Chester Apartment for rent?

Today's apartment with the most square footage in Chester is a 1,350 square feet unit starting from $2,000 at Pulaski.

Expert Rental Resources

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.

Articles, How-To's, and Tips

decorative image for A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back article

A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back

Written by: Lauren Harrington

I’m going to talk with you as a seasoned property manager and friend. So, let’s start with your security deposit. I want you to think about this guide as insider information. You deserve your deposit back.

decorative image for Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts article

Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts

Written by: Lauren Harrington

This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.

decorative image for What Does “Rent Burdened” Mean? How Much Rent Is Too Much article

What Does “Rent Burdened” Mean? How Much Rent Is Too Much

Written by: Lauren Harrington

This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.

decorative image for Maximizing Your Refund: Essential Tax Tips for Renters article

Maximizing Your Refund: Essential Tax Tips for Renters

Written by: Christine Leonard, Esq.

Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.