Luxury Homes for Rent in Chester, CT (21 Rentals)

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

property at 55 Liberty St

$2,500

Total Monthly Price

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

2 Bedroom, 3 Bath Home for Rent

Available Now

55 Liberty St

ChesterCT06412
property at 145 Liberty St

$2,800

Total Monthly Price

Total Monthly Price

Base Rent
$2,800

Total Monthly Price
$2,800

2 Bedroom, 1 Bath Home for Rent

Available Now

145 Liberty St

ClintonCT06413
property at 73 Chapman Beach Rd

$2,800

Total Monthly Price

Total Monthly Price

Base Rent
$2,800

Total Monthly Price
$2,800

2 Bedroom, 1 Bath Home for Rent

Available Now

73 Chapman Beach Rd

WestbrookCT06498
property at 9 Falls River Cir

$2,850

Total Monthly Price

Total Monthly Price

Base Rent
$2,850

Total Monthly Price
$2,850

2 Bedroom, 1 Bath Home for Rent

Available Now

9 Falls River Cir

EssexCT06442
property at 55 Dogwood Rd

$3,150

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,150

Total Monthly Price
$3,150

2 Bedroom, 1 Bath Home for Rent

Available Now

55 Dogwood Rd

East HaddamCT06469
property at 260 Hamburg Rd

$3,200

Total Monthly Price

Total Monthly Price

Base Rent
$3,200

Total Monthly Price
$3,200

5 Bedroom, 1.5 Bath Home for Rent

Available Now

260 Hamburg Rd

LymeCT06371
property at 7 Seascape Dr

$3,300

Total Monthly Price

Total Monthly Price

Base Rent
$3,300

Total Monthly Price
$3,300

4 Bedroom, 2.5 Bath Home for Rent

Available Now

7 Seascape Dr

WestbrookCT06498

Renters Insurance 101: What It Is, What It Covers, and Why You Need It

From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.

property at 6 Bower Rd

$3,500

Total Monthly Price

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

3 Bedroom, 1 Bath Home for Rent

Available Now

6 Bower Rd

MadisonCT06443
property at 6 Leada Woods Rd

$3,500

Total Monthly Price

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

4 Bedroom, 2.5 Bath Home for Rent

Available Sep 1

6 Leada Woods Rd

Old SaybrookCT06475
property at 84 Waterside Ln

$3,600

Total Monthly Price

Total Monthly Price

Base Rent
$3,600

Total Monthly Price
$3,600

1 Bedroom, 2 Bath Condo for Rent

Available Now

84 Waterside Ln

ClintonCT06413
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 166 Harvey Rd

$3,800

Total Monthly Price

Total Monthly Price

Base Rent
$3,800

Total Monthly Price
$3,800

3 Bedroom, 3 Bath Home for Rent

Available Now

166 Harvey Rd

DurhamCT06422
property at 58 Chapman Ave

$3,800

Total Monthly Price

Total Monthly Price

Base Rent
$3,800

Total Monthly Price
$3,800

3 Bedroom, 4 Bath Home for Rent

Available Now

58 Chapman Ave

WestbrookCT06498
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

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.

property at 21 Grove Way

$4,500

Total Monthly Price

Total Monthly Price

Base Rent
$4,500

Total Monthly Price
$4,500

4 Bedroom, 3.5 Bath Home for Rent

Available Now

21 Grove Way

ClintonCT06413
property at 33 Beach Rd W

$4,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,500

Total Monthly Price
$4,500

4 Bedroom, 1.5 Bath Home for Rent

Available Now

33 Beach Rd W

Old SaybrookCT06475
property at 2203 Durham Rd

$5,000

Total Monthly Price

Total Monthly Price

Base Rent
$5,000

Total Monthly Price
$5,000

3 Bedroom, 2 Bath Home for Rent

Available Now

2203 Durham Rd

MadisonCT06443
property at 17 Mallard Dr

$5,000

Total Monthly Price

Total Monthly Price

Base Rent
$5,000

Total Monthly Price
$5,000

4 Bedroom, 2.5 Bath Home for Rent

Available Now

17 Mallard Dr

Old SaybrookCT06475
property at 187 Wildcat Rd

$6,000

Total Monthly Price

Total Monthly Price

Base Rent
$6,000

Total Monthly Price
$6,000

4 Bedroom, 3 Bath Home for Rent

Available Now

187 Wildcat Rd

MadisonCT06443
property at 30 Riverside Ave

$7,500

Total Monthly Price

Total Monthly Price

Base Rent
$7,500

Total Monthly Price
$7,500

3 Bedroom, 3.5 Bath Home for Rent

Available Now

30 Riverside Ave

Old SaybrookCT06475
property at 150 Ferry Rd

$10,000

Total Monthly Price

Total Monthly Price

Base Rent
$10,000

Total Monthly Price
$10,000

3 Bedroom, 3.5 Bath Home for Rent

Available Now

150 Ferry Rd

LymeCT06371

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.

Chester, CT Local Guide

Real Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University

From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.

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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!

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Frequently Asked Questions about Chester

What type of rentals are currently available in Chester?

There are currently 70 Apartments for Rent in Chester, CT with pricing that ranges from $500 to $4,771. There are also 35 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chester ranging from $1,400 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 $1,400 to $10,000 with an average monthly rent of $3,048.

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 Renters Insurance 101: What It Is, What It Covers, and Why You Need It article

Renters Insurance 101: What It Is, What It Covers, and Why You Need It

Written by: Robin Stewart

Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.

decorative image for Apartment Occupancy Rates: Renter Attraction vs Renter Retention   article

Apartment Occupancy Rates: Renter Attraction vs Renter Retention

Written by: Robin Stewart

There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.

decorative image for How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide article

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Written by: Robin Stewart

Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.

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Pet-Friendly Renting: Everything You Need to Know Before You Move

Written by: Christine Leonard, Esq.

For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.