
Luxury Homes for Rent in Chestnut Hill Neighborhood of Boston, MA (319 Rentals)
The most luxurious Homes in the Chestnut Hill area of Boston with high-end amenities, features, and finishes.


2045 Commonwealth Ave, Unit M-46

1933 Commonwealth Ave, Unit 108

247 Chestnut Hill Ave, Unit 5

116 Sutherland Rd, Unit 1

28 Sidlaw Rd, Unit 6

1860 Commonwealth Ave, Unit 51

97 Strathmore Rd, Unit 8

7 Lothian Rd, Unit 3

27 South St, Unit #B3
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.

117 Sutherland Rd, Unit 3

2 Ayr Rd, Unit unitB 1-bed 1-bath

12 Kilsyth Ter, Unit 24

75 Kilsyth Rd

78 Kilsyth Rd, Unit 1

110 Lanark Rd, Unit 7

110 Lanark Rd, Unit 7

110 Lanark Rd, Unit 7

2 Braemore Rd, Unit 1

110 Lanark Rd, Unit 7
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.

2031 Commonwealth Ave, Unit 12

69 Chiswick Rd, Unit 9

63 Selkirk Rd, Unit 1

59 Lanark Rd, Unit 2

39 Englewood Ave, Unit 12

7 Lothian Rd, Unit 12

63 Selkirk Rd, Unit 3

63 Selkirk Rd, Unit 3

2012 Commonwealth Ave, Unit BE

1880 Commonwealth Ave, Unit 12
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.

2001 Commonwealth Ave, Unit 16

39 South St, Unit 4

39 South St, Unit 4

19 Colliston Rd, Unit Apt 3 - 19 Colliston Rd.

370 Chestnut Hill Ave

39 South St, Unit 2

2009 Commonwealth Ave, Unit 20

1950 Beacon St, Unit 1

7 Sutherland Rd, Unit 202

1880 Commonwealth Ave, Unit 14
Smart Renter's Guide: Calculating Affordable Rent & Housing Costs
Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

1872 Commonwealth Ave, Unit 10

1880 Commonwealth Ave, Unit 5

1872 Commonwealth Ave

145 Englewood Ave, Unit 2##

1933 Commonwealth Ave, Unit 1

130 Englewood Ave, Unit 4

10 Selkirk Rd, Unit 4

374 Chestnut Hill Ave, Unit 41

26 Chiswick Rd, Unit 13

141 Chiswick Rd, Unit B
Navigating the Rental Market: Tips for First-Time Renters
Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.
Chestnut Hill, Boston, 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 | $3,241 | $2,295 | $4,850 |
| Chestnut Hill 3 Bedroom Homes for Rent | $4,201 | $2,750 | $5,600 |
| Chestnut Hill 4 Bedroom Homes for Rent | $5,201 | $900 | $10,000+ |
| Chestnut Hill 5 Bedroom Homes for Rent | $7,418 | $4,300 | $10,000+ |
| Chestnut Hill 6 Bedroom Homes for Rent | $7,288 | $1,060 | $10,000+ |
Browse Homes for Rent in this Neighborhood
There are currently 319 rentals with your search options within a 1 mile radius of the Chestnut Hill Neighborhood of Boston, MA.
Explore Boston
Frequently Asked Questions about Chestnut Hill
What type of rentals are currently available in Chestnut Hill?
There are currently 491 Apartments for Rent in Chestnut Hill, MA with pricing that ranges from $1,150 to $14,200. There are also 386 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill ranging from $900 to $17,500.
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 $900 to $17,500 with an average monthly rent of $6,770.
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 $2,700 to $6,380, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,750 to $5,600. Four Bedroom Single-Family rentals are also available starting from $900 and Four Bedroom Apartments start at $3,500.
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

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.

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.

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.

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