Homes for Rent in Chesterfield, MA (40 Rentals)

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property at 20 Maine Ave

$2,000

Total Monthly Price

Total Monthly Price

Base Rent
$2,000

Total Monthly Price
$2,000

2 Bedroom, 2 Bath Condo for Rent

Available Now

20 Maine Ave

EasthamptonMA01027
property at 51 1/2 Hatfield St

$2,200

Total Monthly Price

Total Monthly Price

Base Rent
$2,200

Total Monthly Price
$2,200

2 Bedroom, 1.5 Bath Condo for Rent

Available Now

51 1/2 Hatfield St

NorthamptonMA01060
property at 22 Highland Ave

$2,300

Total Monthly Price

Total Monthly Price

Base Rent
$2,300

Total Monthly Price
$2,300

3 Bedroom, 1.5 Bath Townhome for Rent

Available Now

22 Highland Ave

NorthamptonMA01060
property at 24 Highland Ave

$2,300

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,300

Total Monthly Price
$2,300

3 Bedroom, 1 Bath Townhome for Rent

Available Now

24 Highland Ave

NorthamptonMA01060
property at 123-125 Williams St

$2,795

Total Monthly Price

Total Monthly Price

Base Rent
$2,795

Total Monthly Price
$2,795

3 Bedroom, 1 Bath Condo for Rent

Available Jan 1, 2026

123-125 Williams St

NorthamptonMA01060
property at 16 Winslow Ave

$2,950

Total Monthly Price

Total Monthly Price

Base Rent
$2,950

Total Monthly Price
$2,950

3 Bedroom, 2 Bath Home for Rent

Available Mar 1, 2026

16 Winslow Ave

NorthamptonMA01062
property at 97 Oak St

$2,950

Total Monthly Price

Total Monthly Price

Base Rent
$2,950

Total Monthly Price
$2,950

4 Bedroom, 2 Bath Home for Rent

Available Now

97 Oak St

NorthamptonMA01062
property at 60 Bridge St

$2,950

Total Monthly Price

Total Monthly Price

Base Rent
$2,950

Total Monthly Price
$2,950

3 Bedroom, 1 Bath Home for Rent

Available Now

60 Bridge St

HatfieldMA01038
property at 3238 Main St

$2,500

Total Monthly Price

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

3 Bedroom, 2 Bath Home for Rent

Available Now

3238 Main St

BecketMA01223
property at 131 Lane Rd

$2,550

Total Monthly Price

Total Monthly Price

Base Rent
$2,550

Total Monthly Price
$2,550

2 Bedroom, 1.5 Bath Home for Rent

Available Now

131 Lane Rd

BecketMA01223

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property at 130 West St

$3,895

Total Monthly Price

Total Monthly Price

Base Rent
$3,895

Total Monthly Price
$3,895

4 Bedroom, 1 Bath Condo for Rent

Available Jun 1, 2026

130 West St

HadleyMA01035
property at 190 Russell St

$3,895

Total Monthly Price

Total Monthly Price

Base Rent
$3,895

Total Monthly Price
$3,895

4 Bedroom, 1 Bath Condo for Rent

Available Aug 1, 2026

190 Russell St

HadleyMA01035
property at 201 Middle St

$3,950

Total Monthly Price

Total Monthly Price

Base Rent
$3,950

Total Monthly Price
$3,950

4 Bedroom, 2 Bath Condo for Rent

Available Jun 1, 2026

201 Middle St

HadleyMA01035
property at 132 Middle St

$3,950

Total Monthly Price

Total Monthly Price

Base Rent
$3,950

Total Monthly Price
$3,950

4 Bedroom, 2 Bath Condo for Rent

Available Aug 1, 2026

132 Middle St

HadleyMA01035
property at 456 River Dr

$4,500

Total Monthly Price

Total Monthly Price

Base Rent
$4,500

Total Monthly Price
$4,500

4 Bedroom, 1.5 Bath Home for Rent

Available Jul 1, 2026

456 River Dr

HadleyMA01035
property at 74 Linden St

$2,000

Total Monthly Price

Total Monthly Price

Base Rent
$2,000

Total Monthly Price
$2,000

3 Bedroom, 1 Bath Townhome for Rent

Available Now

74 Linden St

HolyokeMA01040
property at 270 Walnut St

$2,000

Total Monthly Price

Total Monthly Price

Base Rent
$2,000

Total Monthly Price
$2,000

3 Bedroom Rentals

Available Jan 1, 2026

270 Walnut St

HolyokeMA01040
property at 71 Bemis Rd

$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

71 Bemis Rd

HolyokeMA01040
property at 27 Lathrop St

$2,350

Total Monthly Price

Total Monthly Price

Base Rent
$2,350

Total Monthly Price
$2,350

3 Bedroom, 2 Bath Home for Rent

Available Now

27 Lathrop St

South HadleyMA01075
property at 26 Summit St

$2,400

Total Monthly Price

Total Monthly Price

Base Rent
$2,400

Total Monthly Price
$2,400

3 Bedroom, 1 Bath Home for Rent

Available Now

26 Summit St

South HadleyMA01075

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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 46 Old Amherst Rd

$2,895

Total Monthly Price

Total Monthly Price

Base Rent
$2,895

Total Monthly Price
$2,895

3 Bedroom, 1 Bath Condo for Rent

Available Jul 1, 2026

46 Old Amherst Rd

SunderlandMA01375
property at 180 Amherst Rd

$4,995

Total Monthly Price

Total Monthly Price

Base Rent
$4,995

Total Monthly Price
$4,995

5 Bedroom, 2 Bath Home for Rent

Available Jul 1, 2026

180 Amherst Rd

SunderlandMA01375
property at 28 School St

$4,995

Total Monthly Price

Total Monthly Price

Base Rent
$4,995

Total Monthly Price
$4,995

5 Bedroom, 2 Bath Home for Rent

Available Jun 1, 2026

28 School St

SunderlandMA01375
property at 77 Cranston St

$2,100

Total Monthly Price

Total Monthly Price

Base Rent
$2,100

Total Monthly Price
$2,100

3 Bedroom, 1 Bath Townhome for Rent

Available Now

77 Cranston St

WestfieldMA01085
property at 240 Russellville Rd

$2,500

Total Monthly Price

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

3 Bedroom, 1 Bath Home for Rent

Available Now

240 Russellville Rd

WestfieldMA01085
property at 1277 Southampton Rd

$2,500

Total Monthly Price

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

3 Bedroom, 2 Bath Condo for Rent

Available Now

1277 Southampton Rd

WestfieldMA01085
property at 25 Graves St

$2,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,600

Total Monthly Price
$2,600

3 Bedroom, 1.5 Bath Home for Rent

Available Now

25 Graves St

DeerfieldMA01373
property at 25 Greenleaves Dr

$1,550

Total Monthly Price

Total Monthly Price

Base Rent
$1,550

Total Monthly Price
$1,550

1 Bedroom, 1 Bath Condo for Rent

Available Now

25 Greenleaves Dr

AmherstMA01002
property at 252 West St

$1,900

Total Monthly Price

Total Monthly Price

Base Rent
$1,900

Total Monthly Price
$1,900

2 Bedroom, 1 Bath Townhome for Rent

Available Now

252 West St

AmherstMA01002
property at 1 Salem Pl

$2,400

Total Monthly Price

Total Monthly Price

Base Rent
$2,400

Total Monthly Price
$2,400

2 Bedroom, 2.5 Bath Townhome for Rent

Available Jun 3, 2026

1 Salem Pl

AmherstMA01002

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 2 Southpoint Dr

$2,450

Total Monthly Price

Total Monthly Price

Base Rent
$2,450

Total Monthly Price
$2,450

2 Bedroom, 1.5 Bath Townhome for Rent

Available Now

2 Southpoint Dr

AmherstMA01002
property at 17 Southpoint Dr

$2,450

Total Monthly Price

Total Monthly Price

Base Rent
$2,450

Total Monthly Price
$2,450

2 Bedroom, 1.5 Bath Townhome for Rent

Available Now

17 Southpoint Dr

AmherstMA01002
property at 6 Southpoint Dr

$2,550

Total Monthly Price

Total Monthly Price

Base Rent
$2,550

Total Monthly Price
$2,550

2 Bedroom, 1.5 Bath Townhome for Rent

Available Now

6 Southpoint Dr

AmherstMA01002
property at 1 Southpoint Dr

$2,550

Total Monthly Price

Total Monthly Price

Base Rent
$2,550

Total Monthly Price
$2,550

2 Bedroom, 1.5 Bath Townhome for Rent

Available Now

1 Southpoint Dr

AmherstMA01002
property at 47 Southpoint Dr

$2,550

Total Monthly Price

Total Monthly Price

Base Rent
$2,550

Total Monthly Price
$2,550

2 Bedroom, 1.5 Bath Townhome for Rent

Available Now

47 Southpoint Dr

AmherstMA01002
property at 81 Southpoint Dr

$2,550

Total Monthly Price

Total Monthly Price

Base Rent
$2,550

Total Monthly Price
$2,550

2 Bedroom, 1.5 Bath Townhome for Rent

Available Now

81 Southpoint Dr

AmherstMA01002
property at 67 Southpoint Dr

$2,550

Total Monthly Price

Total Monthly Price

Base Rent
$2,550

Total Monthly Price
$2,550

2 Bedroom, 1.5 Bath Townhome for Rent

Available Now

67 Southpoint Dr

AmherstMA01002
property at 20 Hills Rd

$3,900

Total Monthly Price

Total Monthly Price

Base Rent
$3,900

Total Monthly Price
$3,900

5 Bedroom, 2 Bath Home for Rent

Available Now

20 Hills Rd

AmherstMA01002
property at 106 Pondview Dr

$4,600

Total Monthly Price

Total Monthly Price

Base Rent
$4,600

Total Monthly Price
$4,600

5 Bedroom, 2 Bath Home for Rent

Available Jul 1, 2026

106 Pondview Dr

AmherstMA01002
property at 39 Valley Ln

$6,000

Total Monthly Price

Total Monthly Price

Base Rent
$6,000

Total Monthly Price
$6,000

6 Bedroom, 4 Bath Home for Rent

Available Jun 1, 2026

39 Valley Ln

AmherstMA01002

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.

Chesterfield, MA 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.

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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.

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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 Chesterfield, MA Rentals by Map

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Frequently Asked Questions about Chesterfield

What type of rentals are currently available in Chesterfield?

There are currently 47 Apartments for Rent in Chesterfield, MA with pricing that ranges from $799 to $4,800. There are also 40 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chesterfield ranging from $1,550 to $6,000.

What is the current price range for Rental Homes in Chesterfield?

Today's rental pricing for Homes for Rent, Condos and Townhomes in Chesterfield ranges from $1,550 to $6,000 with an average monthly rent of $3,480.

How much are larger Three and Four Bedroom Rentals in Chesterfield?

For those who are looking for larger living arrangements, Three Bedroom Apartments in Chesterfield range from $825 to $4,100, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,000 to $2,950. Four Bedroom Single-Family rentals are also available starting from $2,950 and Four Bedroom Apartments start at $800.

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.