Luxury Homes for Rent in Chester, CT (20 Rentals)

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

property at 70 Goose Hill Rd
$5,000

Total Monthly Price

Base Rent$5,000

Total Monthly Price$5,000
4 Bedroom, 2 Bath Home for Rent
Available Sep 13

70 Goose Hill Rd

ChesterCT06412
property at 9 Red Bird Trail
$2,500

Total Monthly Price

Base Rent$2,500

Total Monthly Price$2,500
3 Bedroom, 1.5 Bath Home for Rent
Available Now

9 Red Bird Trail

Old SaybrookCT06475
property at 73 Chapman Beach Rd
$2,500

Total Monthly Price

Base Rent$2,500

Total Monthly Price$2,500
2 Bedroom, 1 Bath Home for Rent
Available Now

73 Chapman Beach Rd

WestbrookCT06498
property at 82 Menunketesuck Rd
$2,500

Total Monthly Price

Base Rent$2,500

Total Monthly Price$2,500
4 Bedroom, 1.5 Bath Home for Rent
Available Now
Cost Per Sq.Ft.

82 Menunketesuck Rd

WestbrookCT06498
property at 10 Phelps Ln
$2,600

Total Monthly Price

Base Rent$2,600

Total Monthly Price$2,600
2 Bedroom, 1 Bath Home for Rent
Available Now

10 Phelps Ln

Deep RiverCT06417

Exploring Rental Options: Apartments, Townhomes, and Lofts—Oh My!

Looking for the perfect rental? From apartments and condos to lofts and single family rentals, explore the unique pros and cons of each rental type to help you land in your perfect new place.

property at 4 Elinor Rd
$2,600

Total Monthly Price

Base Rent$2,600

Total Monthly Price$2,600
3 Bedroom, 1.5 Bath Home for Rent
Available Now

4 Elinor Rd

Old SaybrookCT06475
property at 55 Dogwood Rd
$2,800

Total Monthly Price

Base Rent$2,800

Total Monthly Price$2,800
12 Month Lease Term
2 Bedroom, 1 Bath Home for Rent
Available Now

55 Dogwood Rd

East HaddamCT06469
property at 260 Hamburg Rd
$2,950

Total Monthly Price

Base Rent$2,950

Total Monthly Price$2,950
5 Bedroom, 1.5 Bath Home for Rent
Available Now
Cost Per Sq.Ft.

260 Hamburg Rd

LymeCT06371
property at 311 Dennison Rd
$3,000

Total Monthly Price

Base Rent$3,000

Total Monthly Price$3,000
1 Bedroom, 1 Bath Home for Rent
Available Now

311 Dennison Rd

WestbrookCT06498
property at 6 Leeway Dr
$3,000

Total Monthly Price

Base Rent$3,000

Total Monthly Price$3,000
3 Bedroom, 3 Bath Home for Rent
Available Now
Cost Per Sq.Ft.

6 Leeway Dr

WestbrookCT06498
property at 7 Seascape Dr
$3,000

Total Monthly Price

Base Rent$3,000

Total Monthly Price$3,000
4 Bedroom, 2.5 Bath Home for Rent
Available Now
Cost Per Sq.Ft.

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 58 Sill Ln
$3,250

Total Monthly Price

Base Rent$3,250

Total Monthly Price$3,250
2 Bedroom, 1 Bath Home for Rent
Available Now

58 Sill Ln

Old LymeCT06371
property at 68 Otter Cove Dr
$3,500

Total Monthly Price

Base Rent$3,500

Total Monthly Price$3,500
4 Bedroom, 2.5 Bath Home for Rent
Available Now

68 Otter Cove Dr

Old SaybrookCT06475
property at 1281 Durham Rd
$3,750

Total Monthly Price

Base Rent$3,750

Total Monthly Price$3,750
4 Bedroom, 2 Bath Home for Rent
Available Now
Cost Per Sq.Ft.

1281 Durham Rd

MadisonCT06443
property at 166 Harvey Rd
$3,800

Total Monthly Price

Base Rent$3,800

Total Monthly Price$3,800
3 Bedroom, 3 Bath Home for Rent
Available Now
Cost Per Sq.Ft.

166 Harvey Rd

DurhamCT06422
property at 6 Beaver Dam Trail
$3,900

Total Monthly Price

Base Rent$3,900

Total Monthly Price$3,900
4 Bedroom, 2.5 Bath Home for Rent
Available Now

6 Beaver Dam Trail

Old SaybrookCT06475
property at 28 Beach Rd W
$4,500

Total Monthly Price

Base Rent$4,500

Total Monthly Price$4,500
12 Month Lease Term
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

Base Rent$4,500

Total Monthly Price$4,500
4 Bedroom, 3.5 Bath Home for Rent
Available Now
Cost Per Sq.Ft.

21 Grove Way

ClintonCT06413
property at 30 Riverside Ave
$7,500

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

Chester, CT Local Guide

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

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.

Read Article
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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 73 Apartments for Rent in Chester, CT with pricing that ranges from $975 to $4,928. There are also 33 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chester ranging from $1,300 to $7,500.

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 $1,300 to $7,500 with an average monthly rent of $2,958.

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 Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My! article

Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My!

Written by: Robin Stewart

Where do you see yourself? When you think of home, sweet home, are you in a 3/2 apartment? Dreaming of a tall townhome? Maybe an industrial loft heavy on cool vibes is on your visioning board.

decorative image for Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags   article

Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags

Written by: Robin Stewart

Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.

decorative image for First Apartment Regrets: Real Renters Share What They'd Do Differently article

First Apartment Regrets: Real Renters Share What They'd Do Differently

Written by: Robin Stewart

Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.

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.