Homes for Rent in Chester, CT (39 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.
By AmenitiesDone
By Community TypeDone
Done
property at 15 Laurel St

$2,200

Total Monthly Price

Total Monthly Price

Base Rent
$2,200

Total Monthly Price
$2,200

3 Bedroom, 1 Bath Home for Rent

Available Now

15 Laurel St

ChesterCT06412
property at 55 Liberty St

$2,500

Total Monthly Price

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

2 Bedroom, 2.5 Bath Home for Rent

Available Now

55 Liberty St

ChesterCT06412
property at 55 Liberty St

$2,500

Plus Fees

2 Bedroom, 3 Bath Home for Rent

Available Now

55 Liberty St

ChesterCT06412
property at 10 Plains Rd

$2,250

Total Monthly Price

Total Monthly Price

Base Rent
$2,250

Total Monthly Price
$2,250

3 Bedroom, 1 Bath Home for Rent

Available Now

10 Plains Rd

East HaddamCT06469
property at 55 Dogwood Rd

$2,450

Total Monthly Price

Total Monthly Price

Base Rent
$2,450

Total Monthly Price
$2,450

2 Bedroom, 1 Bath Home for Rent

Available Now

55 Dogwood Rd

East HaddamCT06469
property at 66 Haywardville Rd

$2,750

Total Monthly Price

Total Monthly Price

Base Rent
$2,750

Total Monthly Price
$2,750

3 Bedroom, 1.5 Bath Home for Rent

Available Now

66 Haywardville Rd

East HaddamCT06423
property at 620 Town St

$2,800

Total Monthly Price

Total Monthly Price

Base Rent
$2,800

Total Monthly Price
$2,800

3 Bedroom, 2 Bath Home for Rent

Available Now

620 Town St

East HaddamCT06469
property at 740 Little City Rd

$3,200

Total Monthly Price

Total Monthly Price

Base Rent
$3,200

Total Monthly Price
$3,200

2 Bedroom, 2 Bath Home for Rent

Available Now

740 Little City Rd

HaddamCT06441

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.

property at 117 Church Hill Rd

$3,300

Total Monthly Price

Total Monthly Price

Base Rent
$3,300

Total Monthly Price
$3,300

3 Bedroom, 2 Bath Home for Rent

Available Now

117 Church Hill Rd

HaddamCT06438
property at 114 Lakeside Dr

$3,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

2 Bedroom, 1 Bath Home for Rent

Available Now

114 Lakeside Dr

East HaddamCT06423
property at 255 Rte 80

$1,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,600

Total Monthly Price
$1,600

1 Bedroom, 1 Bath Home for Rent

Available Now

255 Rte 80

KillingworthCT06419
property at 8 Jacob Ln

$9,950

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$9,950

Total Monthly Price
$9,950

5 Bedroom, 3 Bath Home for Rent

Available Now

8 Jacob Ln

KillingworthCT06419
property at 33 Main St

$1,750

Total Monthly Price

Total Monthly Price

Base Rent
$1,750

Total Monthly Price
$1,750

1 Bedroom, 1 Bath Home for Rent

Available Now

33 Main St

EssexCT06442
property at 25 Park Rd

$1,795

Total Monthly Price

Total Monthly Price

Base Rent
$1,795

Total Monthly Price
$1,795

1 Bedroom, 1 Bath Home for Rent

Available Now

25 Park Rd

EssexCT06442
property at 70 Pond Meadow Rd

$1,800

Total Monthly Price

Total Monthly Price

Base Rent
$1,800

Total Monthly Price
$1,800

2 Bedroom, 1 Bath Condo for Rent

Available Now

70 Pond Meadow Rd

EssexCT06442
property at 190 Westbrook Rd

$2,800

Total Monthly Price

Total Monthly Price

Base Rent
$2,800

Total Monthly Price
$2,800

2 Bedroom, 2 Bath Condo for Rent

Available Now

190 Westbrook Rd

EssexCT06426
property at 27 S Main St

$3,200

Total Monthly Price

Total Monthly Price

Base Rent
$3,200

Total Monthly Price
$3,200

3 Bedroom, 2.5 Bath Condo for Rent

Available Now

27 S Main St

EssexCT06426

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.

property at 33 Prospect St

$3,500

Total Monthly Price

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

2 Bedroom, 2 Bath Home for Rent

Available Now

33 Prospect St

EssexCT06426
property at 1742 Boston Post Rd

$1,900

Total Monthly Price

Total Monthly Price

Base Rent
$1,900

Total Monthly Price
$1,900

2 Bedroom, 1 Bath Condo for Rent

Available Now

1742 Boston Post Rd

WestbrookCT06498
property at 9 Essex Rd

$2,300

Total Monthly Price

Total Monthly Price

Base Rent
$2,300

Total Monthly Price
$2,300

3 Bedroom, 1 Bath Home for Rent

Available Now

9 Essex Rd

WestbrookCT06498
property at 92 Grove Beach Rd S

$2,700

Total Monthly Price

Total Monthly Price

Base Rent
$2,700

Total Monthly Price
$2,700

3 Bedroom, 1.5 Bath Home for Rent

Available Now

92 Grove Beach Rd S

WestbrookCT06498
property at 6 Leeway Dr

$3,999

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,999

Total Monthly Price
$3,999

3 Bedroom, 3 Bath Home for Rent

Available Now

6 Leeway Dr

WestbrookCT06498
property at 173 Captains Dr

$4,575

Total Monthly Price

Total Monthly Price

Base Rent
$4,575

Total Monthly Price
$4,575

4 Bedroom, 3 Bath Home for Rent

Available Now

173 Captains Dr

WestbrookCT06498
property at 293 Hamburg Rd

$2,800

Total Monthly Price

Total Monthly Price

Base Rent
$2,800

Total Monthly Price
$2,800

3 Bedroom, 1 Bath Home for Rent

Available Now

293 Hamburg Rd

LymeCT06371
property at 126 Beaver Brook Rd

$2,850

Total Monthly Price

Total Monthly Price

Base Rent
$2,850

Total Monthly Price
$2,850

1 Bedroom, 1 Bath Home for Rent

Available Now

property at 150 Ferry Rd

$5,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,000

Total Monthly Price
$5,000

3 Bedroom, 3.5 Bath Home for Rent

Available Now

150 Ferry Rd

LymeCT06371

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.

property at 119 Kelseytown Rd

$1,250

Total Monthly Price

Total Monthly Price

Base Rent
$1,250

Total Monthly Price
$1,250

1 Bedroom, 1 Bath Home for Rent

Available Now

119 Kelseytown Rd

ClintonCT06413
property at 144 E Main St

$1,995

Total Monthly Price

Total Monthly Price

Base Rent
$1,995

Total Monthly Price
$1,995

2 Bedroom, 1 Bath Townhome for Rent

Available Jan 1, 2026

144 E Main St

ClintonCT06413
property at 248 Killingworth Turnpike

$2,000

Total Monthly Price

Total Monthly Price

Base Rent
$2,000

Total Monthly Price
$2,000

1 Bedroom, 1 Bath Home for Rent

Available Now

property at 69 Waterside Ln

$2,400

Total Monthly Price

Total Monthly Price

Base Rent
$2,400

Total Monthly Price
$2,400

1 Bedroom, 1 Bath Home for Rent

Available Now

69 Waterside Ln

ClintonCT06413
property at 101 Legend Hill Rd

$3,000

Total Monthly Price

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000

2 Bedroom, 2 Bath Condo for Rent

Available Now

101 Legend Hill Rd

MadisonCT06443
property at 5 Beaver Dam Trail

$3,000

Total Monthly Price

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000

4 Bedroom, 2.5 Bath Home for Rent

Available Now

5 Beaver Dam Trail

Old SaybrookCT06475
property at 156 Concord Dr

$3,500

Total Monthly Price

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

3 Bedroom, 2 Bath Home for Rent

Available Now

156 Concord Dr

MadisonCT06443
property at 1281 Durham Rd

$3,750

Total Monthly Price

Total Monthly Price

Base Rent
$3,750

Total Monthly Price
$3,750

4 Bedroom, 2 Bath Home for Rent

Available Now

1281 Durham Rd

MadisonCT06443
property at 138 School House Rd

$3,800

Total Monthly Price

Total Monthly Price

Base Rent
$3,800

Total Monthly Price
$3,800

2 Bedroom, 3 Bath Home for Rent

Available Now

138 School House Rd

Old SaybrookCT06475

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.

property at 101 Cow Hill Rd

$3,995

Total Monthly Price

Total Monthly Price

Base Rent
$3,995

Total Monthly Price
$3,995

4 Bedroom, 2.5 Bath Home for Rent

Available Now

101 Cow Hill Rd

ClintonCT06413
property at 28 Beach Rd W

$4,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,500

Total Monthly Price
$4,500

2 Bedroom, 2 Bath Home for Rent

Available Now

28 Beach Rd W

Old SaybrookCT06475
property at 7 Saye St

$6,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,000

Total Monthly Price
$6,000

3 Bedroom, 2 Bath Home for Rent

Available Now

7 Saye St

Old SaybrookCT06475

Chester, CT Local Guide

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

How a Move-In Inspection Can Protect Your Security Deposit

Learn How a Move-In Inspection Can Protect Your Security Deposit from the Renter University at AparmentHomeLiving.com.

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, CT Rentals by Map

View Map
Chester, CT Apartments Map
View Map
Chester, CT Rental Homes Map

Frequently Asked Questions about Chester

What type of rentals are currently available in Chester?

There are currently 65 Apartments for Rent in Chester, CT with pricing that ranges from $710 to $4,301. There are also 39 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chester ranging from $1,250 to $9,950.

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 $1,250 to $9,950 with an average monthly rent of $4,367.

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 $1,700 to $3,895, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,200 to $6,000. Four Bedroom Single-Family rentals are also available starting from $3,000 and Four Bedroom Apartments start at $2,400.

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 Renting with Roommates: Realistic Expectations for Shared Lease article

Renting with Roommates: Realistic Expectations for Shared Lease

Written by: Christine Leonard, Esq.

Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.

decorative image for Apartment Common Area Rules: What Renters Need to Know article

Apartment Common Area Rules: What Renters Need to Know

Written by: Christine Leonard, Esq.

Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.

decorative image for How to Negotiate Your Apartment Lease and Save Money article

How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate! 

decorative image for The Rental Move-In Inspection Checklist: A Guide for Renters article

The Rental Move-In Inspection Checklist: A Guide for Renters

Written by: Trey Huguley

The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.