
Homes for Rent in Chestnut Hill, MA with Swimming Pool (99 Rentals) Page 2 of 2


99 Pleasant St, Unit 1-2

50 Watertown St, Unit 2bed 2bath

144 Kenrick St, Unit 24

276 Corey Rd, Unit 12A

26 Commonwealth Terrace, Unit 3

19 Winchester St

50 Green St

132 Yarmouth Rd
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.

20 Hammond Pond Pkwy

50-56-56 Broadlawn Park

25 Westgate Rd

137 Lake Shore Rd

280 Corey Rd

18 Lake Shore Terrace
15 N Beacon St

241 Perkins St

151 Coolidge 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.

36 Risley Rd

51 Algonquin Rd

3 Oakley Rd

69 Walnut St, Unit 6

4 Mossdale Rd

31 Harris St, Unit 102

221 Belgrade Ave, Unit 2

35 Eliot St

567 Poplar St
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.

40 Naples Rd, Unit B

13 Pratt St, Unit 1

12 Vinal St, Unit 3
28 Beaconsfield Rd, Unit 1

753 Boylston St, Unit 2

38 Cumberland Ave

79 Franklin St, Unit 2

20 Shanley St, Unit 1R

142 Bigelow St, Unit 304
Boston's Best Affordable Neighborhoods
Learn about Boston and the best places to live around the area with original content written by our Boston, MA Local Expert Amelia Ramstead

68 Bryon Rd, Unit 5

530 VFW Parkway, Unit 201

120 Washington St, Unit 2

30 Penniman Rd, Unit 203

15 Rushmore St, Unit 15

1304-1312-1312 Commonwealth Ave, Unit 6

414 Western Ave

85 Brainerd Rd, Unit 404

50-56-56 Broadlawn Park, Unit 221
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.

99 Chestnut Hill Ave, Unit 105

38 Lake Shore Terrace, Unit 2

53 Breck Ave

1743 Commonwealth Ave
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
Frequently Asked Questions about Chestnut Hill
What type of rentals are currently available in Chestnut Hill?
There are currently 2392 Apartments for Rent in Chestnut Hill, MA with pricing that ranges from $800 to $13,500. There are also 4120 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 $1,495 to $12,705, 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.