
Luxury Homes for Rent in Chestnut Hill Neighborhood of Boston, MA (546 Rentals)
Higher End Luxurious Homes in the Chestnut Hill area of Boston.


27 Orkney Rd, Unit 1

27 Orkney Rd, Unit 1

12 Gerald Rd

37 Radnor Rd, Unit 1

49 Radnor Rd, Unit 1

45 Radnor Rd

12 Gerald Rd, Unit 1

2021 Commonwealth Ave, Unit D

1860 Commonwealth Ave, Unit 1
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.

1860 Commonwealth Avenue

2021 Commonwealth Ave, Unit A

117 Sutherland Rd

58 Englewood Ave, Unit 1

25 Wade St

11 Kinross Rd, Unit 2

129 Sutherland

129 Sutherland Rd

129 Sutherland Rd

129 Sutherland
Know Your Rights - How Discrimination Laws Impact Landlords and Tenants
Read our practical guide to landlord and tenant rights. Understand protected classes, reasonable accommodations, and legal exceptions to prevent housing discrimination.

129 Sutherland Rd

129 Sutherland Rd

21 Radnor Rd

48 Englewood Ave, Unit 1

45 Radnor Rd, Unit 2

229 Chestnut Hill Ave, Unit 2

53 Radnor Rd, Unit 2

229 Chestnut Hill Ave, Unit 2

1914 Beacon St

1914 Beacon St, Unit 2
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

6 Lothian Rd, Unit 2

229 Chestnut Hill Ave, Unit Uni1 4-bed 2-bath

154 Kilsyth Rd

154 Kilsyth Rd, Unit 154a

154 Kilsyth Rd, Unit 1

154 Kilsyth Rd, Unit T

154 Kilsyth Rd

59 Strathmore Rd, Unit 4

99 Kilsyth Rd, Unit 2

217 Chestnut Hill Ave, Unit 3

99 Kilsyth Rd

99 Kilsyth Rd

99 Kilsyth Rd, Unit 2

47 Orkney Rd, Unit 2

27 Orkney Rd, Unit 2

47 Orkney Rd, Unit 2

27 Orkney Rd

45 Orkney Rd, Unit 3

27 Orkney Rd, Unit 27

7 Kilsyth Ter
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 | $3,281 | $2,200 | $6,500 |
Chestnut Hill 3 Bedroom Homes for Rent | $4,163 | $2,895 | $7,500 |
Chestnut Hill 4 Bedroom Homes for Rent | $5,422 | $3,525 | $10,000+ |
Chestnut Hill 5 Bedroom Homes for Rent | $6,297 | $4,500 | $10,000+ |
Chestnut Hill 6 Bedroom Homes for Rent | $10,030 | $6,900 | $10,000+ |
Browse Homes for Rent in this Neighborhood
There are currently 546 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 749 Apartments for Rent in Chestnut Hill, MA with pricing that ranges from $950 to $25,723. There are also 663 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill ranging from $1,750 to $15,000.
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 $1,750 to $15,000 with an average monthly rent of $4,847.
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 $2,500 to $8,655, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,895 to $7,500. Four Bedroom Single-Family rentals are also available starting from $3,525 and Four Bedroom Apartments start at $1,025.
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.

Navigating the Rental Market: Tips for First-Time Renters
Written by: Sandy Baker
Making the decision to rent is exciting and terrifying at the same time. For many people, there are a lot of unknowns.

Rise of Digital Nomads: Remote Work Tips for Apartment Renters
Written by: Brandie Parton
As a digital nomad, you no longer call a set address or office building your home for eight hours of the day or more.

Know Your Rights - How Discrimination Laws Impact Landlords and Tenants
Written by: Christine Leonard, Esq.
Everyone needs a place to live and to call home. For decades, the federal government has established protections to ensure that individuals and families can find housing free from discriminatory barriers.