
Homes for Rent in Chestnut Hill, MA with Swimming Pool (140 Rentals)


97 Sherman Rd

79 Thornton Rd, Unit 79, Unit 79

194 Gerry Rd

527 Vfw Pky

59 Thornton Rd

607 Vfw Pky

46 Gerry Rd

33 Gerry Rd

130 Sherman Rd, Unit 130, Unit 130
Apartment Common Area Rules: What Renters Need to Know
From the lounge to the laundry room, understand your rights and responsibilities in shared apartment spaces. Get tips on pet rules, noise, and security.

148 Independence Dr

241 Gerry Rd

499 Vfw Pky

122 Independence Dr

120 Thornton Rd

29 Independence Dr

250 Hammond Pond Pky, Unit 1203N, Unit 1203N

203 Ellery Ct

93 Woodcliff Rd, Unit 1, Unit 1

33 Westgate Rd, Unit 5, Unit 5
Understanding Amenity Fees: Know Where You Might Be Able to Save Money
What are amenity fees and are they optional? This guide breaks down everything you need to know about apartment amenity fees, including when you can opt out and how you might be able to lower your rent.

50 Broadlawn Park, Unit 307, Unit 307

57 Broadlawn Park, Unit 20B, Unit 20B

44 Broadlawn Park, Unit 18B, Unit 18B

28 Bryon Rd, Unit 1, Unit 1

31 Westgate Rd, Unit 5, Unit 5

589 Vfw Pky

537 Vfw Pky

162 Sherman Rd

50 Broadlawn Park, Unit 410, Unit 410

533 Vfw Pky
It's time to soak up some sun!
One of the easiest and more obvious ways of enjoying the summer sun is to lounge out by your community pool. Learn a Few Rules to Keep in Mind while at the pool.

44 Washington St, Unit 309, Unit 309

50 Green St

50 Green St, Unit 114, Unit 114

77 Pond Ave, Unit 612, Unit 612

38 Juniper St, Unit 78, Unit 78

33 Pond Ave, Unit 813, Unit 813

19 Winchester St, Unit 512, Unit 512

33 Pond Ave

1731 Beacon St, Unit 420, Unit 420

99 Pond Ave, Unit 213, Unit 213
Boston Major Employer Neighborhood Guide: Living Near UMass, MGH, & State Street
Get the local scoop! ApartmentHomeLiving's Boston Expert reveals the best neighborhoods to rent for employees of UMass Boston, Mass General Hospital, State Street, and more.

22 Chestnut Pl, Unit 403, Unit 403

33 Pond Ave, Unit 309, Unit 309

1731 Beacon St, Unit 203, Unit 203

1731 Beacon St, Unit 422, Unit 422

45 Longwood Ave, Unit 210, Unit 210

20 Webster St, Unit 405, Unit 405

1731 Beacon St, Unit 711, Unit 711

1731 Beacon St, Unit 108, Unit 108

1485 Beacon St, Unit 708, Unit 708

1441 Beacon St, Unit 601, Unit 601
Explore Like a Local: The Insider's Guide to Boston
Explore Boston like a local with our guide to neighborhoods, history, and hidden gems. Discover the city's best apartments, from historic brownstones to modern high-rises, and find your perfect Boston home.
Chestnut Hill, MA Local Guide

How much does it cost to rent a home in Chestnut Hill?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Chestnut Hill 2 Bedroom Homes for Rent | $3,239 | $1,450 | $8,250 |
| Chestnut Hill 3 Bedroom Homes for Rent | $4,055 | $1,250 | $10,000+ |
| Chestnut Hill 4 Bedroom Homes for Rent | $4,744 | $980 | $10,000+ |
| Chestnut Hill 5 Bedroom Homes for Rent | $5,757 | $1,010 | $10,000+ |
| Chestnut Hill 6 Bedroom Homes for Rent | $6,410 | $925 | $10,000+ |
| Chestnut Hill 7 Bedroom Homes for Rent | $3,162 | $1,025 | $10,000+ |
Browse Top Homes for Rent in Chestnut Hill
Explore Chestnut Hill
Chestnut Hill, MA Local Guide
- Nearby Cities
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- School Districts
Boston Neighborhood Guide: Living Near UMass, MGH, and State Street
Get the local scoop! ApartmentHomeLiving's Boston Expert reveals the best neighborhoods to rent for employees of UMass Boston, Mass General Hospital, State Street, and more.
Read ArticleTop Neighborhoods Near Boston Colleges and Universities
Learn About the Best Neighborhoods to Rent Near College Campuses in Boston, MA | Find Boston Off-Campus Student Housing at ApartmentHomeLiving.com
Read ArticleReal 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 ArticleQuick 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.
Remember the 3 Rules of Real Estate:Location, Location, Location!
Explore Chestnut Hill, MA Rentals by Map
See the most popular apartments and homes in Chestnut Hill, MA
Frequently Asked Questions about Chestnut Hill
What type of rentals are currently available in Chestnut Hill?
There are currently 4273 Apartments for Rent in Chestnut Hill, MA with pricing that ranges from $1,000 to $21,950. There are also 4876 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill ranging from $925 to $30,000.
What is the current price range for Rental Homes in Chestnut Hill?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Chestnut Hill ranges from $925 to $30,000 with an average monthly rent of $4,586.
How much are larger Three and Four Bedroom Rentals in Chestnut Hill?
For those who are looking for larger living arrangements, Three Bedroom Apartments in Chestnut Hill range from $1,295 to $16,877, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,250 to $30,000. Four Bedroom Single-Family rentals are also available starting from $980 and Four Bedroom Apartments start at $1,000.
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.
Helpful Local Expert Guides

The 10 Best Affordable Neighborhoods in Boston, MA
Written by: Amelia Ramstead
Boston is known for its exciting combination of early American history and modern high-tech universities and employers.

A Local Experts Guide to the Top Boston Neighborhoods for College Renters
Written by: Amelia Ramstead
Hi! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, Massachusetts! We’re excited to help you find your new home, and getting to know the neighborhood is an important part of that process!

Explore Like a Local: The Insider's Guide to Boston
Written by: Amelia Ramstead
Hello from Boston, Massachusetts! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, and I’m here to give you the inside scoop on this unique city.

Boston Major Employer Neighborhood Guide: Living Near UMass, MGH, & State Street
Written by: Amelia Ramstead
Hi! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, Massachusetts. Getting to know your new neighborhood is one of the best parts of moving, and we’re excited to help you get started.
Articles, How-To's, and Tips

A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back
Written by: Lauren Harrington
I’m going to talk with you as a seasoned property manager and friend. So, let’s start with your security deposit. I want you to think about this guide as insider information. You deserve your deposit back.

Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts
Written by: Lauren Harrington
This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.

What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Written by: Lauren Harrington
This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.

Maximizing Your Refund: Essential Tax Tips for Renters
Written by: Christine Leonard, Esq.
Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.