
Luxury Homes for Rent in Chestnut Hill Neighborhood of Boston, MA (598 Rentals)
The most luxurious Homes in the Chestnut Hill area of Boston with high-end amenities, features, and finishes.


2018 Commonwealth Ave, Unit 45

2 Sutherland Rd, Unit 22

2000 Commonwealth Ave, Unit Commonwealth Ave #45

2045 Commonwealth Ave, Unit M-46

110 Lanark Rd, Unit 6

155 Strathmore Rd, Unit 02

25 South St, Unit 5

61 Selkirk Rd, Unit 4
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.

145 Englewood Ave, Unit 43

90 Kilsyth Rd, Unit 22

65 Strathmore Rd, Unit 5

117 Sutherland Rd, Unit N

1845 Commonwealth Ave, Unit 29

1799 Commonwealth Ave, Unit 20

27 South St, Unit #B3

2012 Commonwealth Ave, Unit 1

36 Orkney Rd, Unit B

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

370 Chestnut Hill Ave, Unit 1
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.

79 Sutherland Rd, Unit 5

117 Sutherland Rd, Unit 3

129 Sutherland Rd, Unit B

5 Braemore Rd, Unit 1-15

131 Sutherland Rd, Unit C

249 Chestnut Hill Ave, Unit 51

2 Braemore Rd, Unit 1

1933 Commonwealth Ave, Unit 108

69 Chiswick Rd, Unit 1

5 Braemore Rd, Unit 8
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.

116 Sutherland Rd, Unit 4

115 Sutherland Rd, Unit E

374 Chestnut Hill Ave, Unit 24

130 Sutherland Rd, Unit A

63 Selkirk Rd, Unit 1

1782 Commonwealth Ave, Unit 1

123 Sutherland Rd, Unit M

84 Kilsyth Rd, Unit 14

59 Lanark Rd, Unit 1

100 Lanark Rd, Unit 1
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

374 Chestnut Hill Ave

90 Kilsyth Rd, Unit 37

59 Lanark Rd, Unit 2

98 Strathmore Rd, Unit 2

59 Lanark Rd, Unit 2

59 Lanark Rd, Unit 2

59 Lanark Rd

59 Lanark Rd, Unit 2

7 Lothian Rd, Unit 8

59 Lanark Rd, Unit 2
Chestnut Hill, Boston, MA Local Guide

How much does it cost to rent a home in Chestnut Hill?
Bedroom | Average Rent | Cheapest Rent | Highest Rent |
---|---|---|---|
Chestnut Hill 2 Bedroom Homes for Rent | $3,321 | $2,300 | $6,500 |
Chestnut Hill 3 Bedroom Homes for Rent | $4,335 | $2,800 | $8,250 |
Chestnut Hill 4 Bedroom Homes for Rent | $4,981 | $950 | $9,000 |
Chestnut Hill 5 Bedroom Homes for Rent | $7,166 | $4,500 | $10,000+ |
Chestnut Hill 6 Bedroom Homes for Rent | $9,572 | $1,150 | $10,000+ |
Browse Homes for Rent in this Neighborhood
There are currently 598 rentals with your search options within a 1 mile radius of the Chestnut Hill Neighborhood of Boston, MA.
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Chestnut Hill, Boston, MA Local Guide
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Quick 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.
Frequently Asked Questions about Chestnut Hill
What type of rentals are currently available in Chestnut Hill?
There are currently 801 Apartments for Rent in Chestnut Hill, MA with pricing that ranges from $1,775 to $14,000. There are also 758 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill ranging from $950 to $40,000.
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 $950 to $40,000 with an average monthly rent of $4,866.
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 $2,600 to $6,900, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,800 to $8,250. Four Bedroom Single-Family rentals are also available starting from $950 and Four Bedroom Apartments start at $3,600.
Expert Rental Resources
Helpful Apartment Articles, How-To's and Tips
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.

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.

Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
Written by: Cheryl Bowman
A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.

The Art of the Rental Viewing: What to look for during a property tour
Written by: Marie Brown
You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.

Know Your Budget: Calculating What You Can Realistically Afford When Renting
Written by: Lauren Harrington
Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.