
Homes for Rent in Chestnut Hill, MA with Swimming Pool (123 Rentals)


607 Vfw Pky

46 Gerry Rd

79 Thornton Rd, Unit 79

194 Gerry Rd

130 Sherman Rd, Unit 130

527 Vfw Pky

59 Thornton Rd

241 Gerry Rd

148 Independence Dr
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.

120 Thornton Rd

33 Gerry Rd

97 Sherman Rd

499 Vfw Pky

29 Independence Dr

250 Hammond Pond Pky, Unit 1203N

33 Westgate Rd, Unit 1

33 Westgate Rd, Unit 5

33 Westgate Rd, Unit 5

23 Westgate Rd, Unit 6
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.

31 Westgate Rd, Unit 5

589 Vfw Pky

162 Sherman Rd

50 Broadlawn Park, Unit 410

50-56 Broadlawn Park, Unit 410

60 Broadlawn Park, Unit 410

44 Washington St, Unit 616

33 Pond Ave, Unit 301

77 Pond Ave, Unit 1010

99 Pond Ave, Unit 902
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.

19 Winchester St, Unit 512

77 Pond Ave, Unit 407

33 Pond Ave, Unit 417

1731 Beacon St, Unit 1213

1731 Beacon St, Unit 422

1731 Beacon St, Unit 203

8 Juniper St, Unit 22

50 Green St, Unit 411

1485 Beacon St, Unit 708

10 Juniper St, Unit 35
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.

50 Green St, Unit 209

77 Pond Ave, Unit 306

20 Webster St, Unit ##

320 Hammond Pond Pkwy, Unit 104

40 Puddingstone Ln

40 Puddingstone Ln

40 Puddingstone Ln

110 Lanark Rd, Unit A

124 Sutherland Rd, Unit 1

26 Commonwealth Ter, Unit 3
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.
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 | $3,164 | $910 | $8,500 |
| Chestnut Hill 3 Bedroom Homes for Rent | $3,984 | $850 | $10,000+ |
| Chestnut Hill 4 Bedroom Homes for Rent | $4,488 | $725 | $10,000+ |
| Chestnut Hill 5 Bedroom Homes for Rent | $5,603 | $760 | $10,000+ |
| Chestnut Hill 6 Bedroom Homes for Rent | $6,708 | $780 | $10,000+ |
| Chestnut Hill 7 Bedroom Homes for Rent | $3,372 | $825 | $10,000+ |
Browse Top Homes for Rent in Chestnut Hill
Explore Chestnut Hill
Chestnut Hill, MA Local Guide
- Nearby Cities
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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 ArticleDon'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 ArticleThe 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.
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 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 4165 Apartments for Rent in Chestnut Hill, MA with pricing that ranges from $375 to $21,050. There are also 3609 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill ranging from $725 to $38,000.
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 $725 to $38,000 with an average monthly rent of $7,459.
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 $950 to $12,500, while Three Bedroom Homes, Condos, and Townhomes for rent range from $850 to $22,000. Four Bedroom Single-Family rentals are also available starting from $725 and Four Bedroom Apartments start at $1,225.
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

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.

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.

How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!

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.