
Homes for Rent in Chestnut Hill, MA with Swimming Pool (133 Rentals)


79 Thornton Rd, Unit 79

97 Sherman Rd

194 Gerry Rd

122 Independence Dr

527 Vfw Pky

59 Thornton Rd

607 Vfw Pky

46 Gerry Rd

33 Gerry Rd
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.

130 Sherman Rd, Unit 130

148 Independence Dr

20 Hammond Pond Pky, Unit 305

241 Gerry Rd

499 Vfw Pky

120 Thornton Rd

29 Independence Dr

250 Hammond Pond Pky, Unit 1203N

203 Ellery Ct

33 Westgate Rd, Unit 5
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.

30 Westgate Rd, Unit 5

28 Bryon Rd, Unit 1

31 Westgate Rd, Unit 5

55 Broadlawn Park, Unit 18

589 Vfw Pky

537 Vfw Pky

162 Sherman Rd

50 Broadlawn Park, Unit 410

50-56 Broadlawn Park, Unit 410

533 Vfw Pky
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.

44 Washington St, Unit 703

50 Green St, Unit 316

50 Green St, Unit 316

50 Green St

33 Pond Ave

44 Washington St, Unit 316

44 Washington St

19 Winchester St, Unit 512

77 Pond Ave, Unit 612

77 Pond Ave
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.

77 Pond Ave, Unit 408

33 Pond Ave, Unit 813

99 Pond Ave, Unit 218

1731 Beacon St, Unit 422

38 Juniper St, Unit 96

32 Juniper St, Unit 96

1485 Beacon St, Unit 708

77 Pond Ave, Unit 306

1731 Beacon St, Unit 1110

10 Juniper St, Unit 35
The Art of the Rental Viewing: What to look for during a property tour
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.
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 | $3,238 | $1,000 | $8,250 |
| Chestnut Hill 3 Bedroom Homes for Rent | $4,006 | $950 | $10,000+ |
| Chestnut Hill 4 Bedroom Homes for Rent | $4,613 | $800 | $10,000+ |
| Chestnut Hill 5 Bedroom Homes for Rent | $5,730 | $775 | $10,000+ |
| Chestnut Hill 6 Bedroom Homes for Rent | $6,719 | $1,000 | $10,000+ |
| Chestnut Hill 7 Bedroom Homes for Rent | $4,627 | $930 | $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
10 Hidden Costs of Renting You Should Budget for Before Signing a Lease
Avoid financial stress when renting. Learn about the 10 most common hidden costs—from pet fees to utilities—you must budget for before you sign a lease.
Read ArticleBoston 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 ArticleCash 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.
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 4692 Apartments for Rent in Chestnut Hill, MA with pricing that ranges from $1,020 to $17,969. There are also 4747 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill ranging from $775 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 $775 to $38,000 with an average monthly rent of $8,530.
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 $17,969, while Three Bedroom Homes, Condos, and Townhomes for rent range from $950 to $30,000. Four Bedroom Single-Family rentals are also available starting from $800 and Four Bedroom Apartments start at $1,295.
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.

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.

18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Written by: Lauren Harrington
Renting your next home can feel thrilling and overwhelming at the same time.

A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment
Written by: Bob Mallory
Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.