Luxury Homes for Rent in Chester, CT (18 Rentals)

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The most luxurious Homes in Chester with high-end amenities, features, and finishes.

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 11 Pinehurst Ln

$2,700

Total Monthly Price

Total Monthly Price

Base Rent
$2,700

Total Monthly Price
$2,700

2 Bedroom Rentals

Available Now

11 Pinehurst Ln

East HaddamCT06469
property at 10 College St

$2,795

Total Monthly Price

Total Monthly Price

Base Rent
$2,795

Total Monthly Price
$2,795

3 Bedroom, 2 Bath Home for Rent

Available Now

10 College St

ClintonCT06413
property at 12 Beach Park Rd

$2,795

Total Monthly Price

Total Monthly Price

Base Rent
$2,795

Total Monthly Price
$2,795

3 Bedroom, 1 Bath Home for Rent

Available Now

12 Beach Park Rd

ClintonCT06413
property at 117 Church Hill Rd

$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

117 Church Hill Rd

HaddamCT06438
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

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 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
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 114 Lakeside Dr

$3,500

Total Monthly Price

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 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 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 158 Captains Dr

$4,025

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,025

Total Monthly Price
$4,025

3 Bedroom, 2 Bath Home for Rent

Available Now

158 Captains Dr

WestbrookCT06498

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 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 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
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
property at 2203 Durham Rd

$7,500

Total Monthly Price

Total Monthly Price

Base Rent
$7,500

Total Monthly Price
$7,500

3 Bedroom, 2 Bath Home for Rent

Available Now

2203 Durham Rd

MadisonCT06443
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 558 N Roast Meat Hill Rd

$10,000

Total Monthly Price

Total Monthly Price

Base Rent
$10,000

Total Monthly Price
$10,000

3 Bedroom, 2 Bath Home for Rent

Available Now

558 N Roast Meat Hill Rd

KillingworthCT06419

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.

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
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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.

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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
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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.

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

Explore Chester, CT Rentals by Map

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Frequently Asked Questions about Chester

What type of rentals are currently available in Chester?

There are currently 66 Apartments for Rent in Chester, CT with pricing that ranges from $710 to $4,457. There are also 35 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chester ranging from $1,100 to $10,000.

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 $1,100 to $10,000 with an average monthly rent of $4,294.

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 18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property article

18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property

Written by: Lauren Harrington

Renting your next home can feel thrilling and overwhelming at the same time.

decorative image for A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment article

A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment

Written by: Bob Mallory

Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.

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.