
Homes for Rent in Chestnut Hill, MA with Swimming Pool (97 Rentals)


194 Gerry Rd

97 Sherman Rd

79 Thornton Rd, Unit 79

527 Vfw Pky

46 Gerry Rd

148 Independence Dr

33 Gerry Rd

130 Sherman Rd, Unit 130

59 Thornton Rd
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241 Gerry Rd

499 Vfw Pky

120 Thornton Rd

29 Independence Dr

607 Vfw Pky

203 Ellery Ct

41 Broadlawn Park

52 Bryon Rd, Unit 3

307 Tappan St, Unit 3

150 Kenrick St, Unit 4
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55 Broadlawn Park, Unit 18

44 Broadlawn Park

589 Vfw Pky

162 Sherman Rd

57 Broadlawn Park, Unit 16

33 Pond Ave

77 Pond Ave, Unit 804
1731 Beacon St, Unit 422
1731 Beacon St, Unit 108
1485 Beacon St, Unit 708
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50 Green St, Unit 109

100 Lanark Rd, Unit A B

92 Gordon St, Unit 205

124 Sutherland Rd, Unit 1

32 Gordon St, Unit 205

100 Lanark Rd, Unit 5

1988 Commonwealth Ave, Unit 62

57 Broadlawn Park, Unit 11

121 Tremont St, Unit 420

14 Heron St, Unit 410
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142 Kenrick St, Unit 38

137 Chiswick Rd, Unit 3

30 Kinross Rd, Unit 2##

51 Lake Shore Ct, Unit 1

35 Lake Shore Ct, Unit 1
15 N Beacon, Unit 228
15 North Beacon St, Unit 503

85 Brainerd Rd, Unit 503

147 Kelton St, Unit 2-bed 2-bath

85 Brainerd Rd
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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 | $3,265 | $2,000 | $10,000+ |
| Chestnut Hill 3 Bedroom Homes for Rent | $4,091 | $900 | $10,000+ |
| Chestnut Hill 4 Bedroom Homes for Rent | $5,083 | $1,110 | $10,000+ |
| Chestnut Hill 5 Bedroom Homes for Rent | $6,050 | $1,280 | $10,000+ |
| Chestnut Hill 6 Bedroom Homes for Rent | $6,542 | $1,100 | $10,000+ |
| Chestnut Hill 7 Bedroom Homes for Rent | $3,906 | $1,110 | $10,000+ |
Browse Top Homes for Rent in Chestnut Hill
Explore Chestnut Hill
Chestnut Hill, MA Local Guide
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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 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 2445 Apartments for Rent in Chestnut Hill, MA with pricing that ranges from $800 to $13,500. There are also 4311 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill ranging from $900 to $99,999.
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 $900 to $99,999 with an average monthly rent of $3,583.
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 $1,033 to $12,535, while Three Bedroom Homes, Condos, and Townhomes for rent range from $900 to $99,999. Four Bedroom Single-Family rentals are also available starting from $1,110 and Four Bedroom Apartments start at $1,350.
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

Moving to Boston Without Losing Your Mind: A Renter’s Guide to a Smooth Move
Written by: Amelia Ramstead
Hello! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston.

What It Really Costs to Live in Boston: A Local Renter's Guide
Written by: Amelia Ramstead
Hello! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston.

Close to Boston, Easier to Rent: Your Guide to 5 Key Neighboring Cities
Written by: Amelia Ramstead
Hello! I’m Amelia, your ApartmentHomeLiving.com expert for Boston!

Top Short-Term Rental Neighborhoods in Boston: Tips from a Local Expert
Written by: Amelia Ramstead
Hi! I’m Amelia, your ApartmentHomeLiving.com expert for Boston, and I’m excited to help you find your next home!
Articles, How-To's, and Tips

Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags
Written by: Robin Stewart
Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.

First Apartment Regrets: Real Renters Share What They'd Do Differently
Written by: Robin Stewart
Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.

Renters Insurance 101: What It Is, What It Covers, and Why You Need It
Written by: Robin Stewart
Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.

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.