
Homes for Rent in Chestnut Hill, MA with Swimming Pool (117 Rentals)


2 Hammond Pond Pky, Unit 604

194 Gerry Rd

97 Sherman Rd

79 Thornton Rd, Unit 79

20 Hammond Pond Pky, Unit 206

59 Thornton Rd

130 Sherman Rd, Unit 130

527 Vfw Pky

46 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.

33 Gerry Rd

148 Independence Dr

241 Gerry Rd

499 Vfw Pky

120 Thornton Rd

29 Independence Dr

607 Vfw Pky

250 Hammond Pond Pky, Unit 1203N

203 Ellery Ct

140 Kenrick St, Unit Apt 23
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

57 Broadlawn Park, Unit 11B

34 Bryon Rd, Unit 3

55 Broadlawn Park, Unit 18

44 Broadlawn Park

589 Vfw Pky

162 Sherman Rd

19 Winchester St, Unit 512
1731 Beacon St, Unit 316
1731 Beacon St, Unit 711
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.

77 Pond Ave, Unit 804
1731 Beacon St, Unit 422
1731 Beacon St, Unit 108
1485 Beacon St, Unit 708

50 Green St, Unit 109

40 Puddingstone Ln

40 Puddingstone Ln

40 Puddingstone Ln

92 Gordon St, Unit 205

124 Sutherland Rd, Unit 1
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.

32 Gordon St, Unit 205

35 Westgate Rd

26 Commonwealth Ter, Unit 3

72 Euston Rd

142 Kenrick St, Unit 38

374 Chestnut Hill Ave, Unit 43

1486 Commonwealth Ave, Unit U:18

30 Kinross Rd, Unit 2##

137 Chiswick Rd, Unit 3

51 Lake Shore Ct, Unit 1
Close to Boston, Easier to Rent: Your Guide to 5 Key Neighboring Cities
Find your perfect apartment outside Boston. We review Quincy, Braintree, Malden, Somerville, and Lynn, covering local hotspots, commute options, and available rental types.
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 | $3,287 | $1,380 | $7,950 |
| Chestnut Hill 3 Bedroom Homes for Rent | $4,095 | $1,330 | $10,000+ |
| Chestnut Hill 4 Bedroom Homes for Rent | $4,721 | $950 | $10,000+ |
| Chestnut Hill 5 Bedroom Homes for Rent | $5,631 | $1,010 | $10,000+ |
| Chestnut Hill 6 Bedroom Homes for Rent | $6,326 | $1,000 | $10,000+ |
| Chestnut Hill 7 Bedroom Homes for Rent | $3,592 | $1,110 | $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 3535 Apartments for Rent in Chestnut Hill, MA with pricing that ranges from $950 to $17,000. There are also 4485 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill ranging from $950 to $35,500.
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 $950 to $35,500 with an average monthly rent of $5,547.
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 $1,350 to $13,207, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,330 to $35,500. Four Bedroom Single-Family rentals are also available starting from $950 and Four Bedroom Apartments start at $1,050.
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 Occupancy Rates: Renter Attraction vs Renter Retention
Written by: Robin Stewart
There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Written by: Robin Stewart
Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.

Pet-Friendly Renting: Everything You Need to Know Before You Move
Written by: Christine Leonard, Esq.
For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.

Creative Ways Developers Reimagine Retail Spaces as Residential Units
Written by: Robin Stewart
Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.