
Luxury Homes for Rent in the Chestnut Hill Neighborhood of Boston, MA (366 Rentals)
The most luxurious Homes in the Chestnut Hill area of Boston with high-end amenities, features, and finishes.


65 Chiswick Rd

7 Lothian Rd

1999 Commonwealth Ave

26 Chiswick Rd

1982 Commonwealth Ave

247 Chestnut Hill Ave

116 Sutherland Rd

48 Strathmore Rd, Unit 26

164 Strathmore Rd, Unit 25
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15 Colliston Rd, Unit 4

27 South St, Unit #B3

9 Braemore Rd, Unit 1A

1933 Commonwealth Ave

37 Radnor Rd

59 Lanark Rd, Unit 12

59 Lanark Rd, Unit 12

1933 Commonwealth Ave, Unit 504

2 Braemore Rd, Unit 1

12 Sutherland Rd, Unit A
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67 Chiswick Rd

15 South St, Unit 15 South

30 Kinross Rd, Unit 2##

72 Strathmore Rd

132 Chiswick Rd, Unit 1B

46 Orkney Rd, Unit #2

1868 Commonwealth Ave, Unit 5DW

1868 Commonwealth Ave, Unit 5

1880 Commonwealth Ave, Unit 5

8 Selkirk Rd
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39 Englewood Ave, Unit 12

292 Foster St, Unit 2

22 Chiswick Rd, Unit 13

1776 Commonwealth Ave, Unit 3

79 Sutherland Rd, Unit 4

72 Strathmore Rd, Unit 3B

2009 Commonwealth Ave, Unit 20

116 Englewood Ave

2001 Commonwealth Ave, Unit 34

78 Kilsyth Rd, Unit 1
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1999 Commonwealth Ave

148 Strathmore Rd, Unit 21

2003 Commonwealth Ave, Unit 20

72 Strathmore Rd

34 Orkney Rd, Unit 9

7 Lothian Rd, Unit 3

370 Chestnut Hill Ave, Unit 35

97 Kilsyth Rd, Unit 4
1942 Beacon St, Unit 4

39 Englewood Ave, Unit #4
How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.
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 | $3,086 | $2,250 | $6,000 |
| Chestnut Hill 3 Bedroom Homes for Rent | $3,782 | $2,475 | $6,900 |
| Chestnut Hill 4 Bedroom Homes for Rent | $5,323 | $1,200 | $10,000+ |
| Chestnut Hill 5 Bedroom Homes for Rent | $6,681 | $4,700 | $10,000+ |
| Chestnut Hill 6 Bedroom Homes for Rent | $6,455 | $975 | $10,000+ |
| Chestnut Hill 7 Bedroom Homes for Rent | $10,500 | $10,000 | $10,000+ |
Browse Homes for Rent in this Neighborhood
There are currently 366 rentals with your search options within a 1 mile radius of the Chestnut Hill Neighborhood of Boston, MA.
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Frequently Asked Questions about Chestnut Hill
What type of rentals are currently available in Chestnut Hill?
There are currently 298 Apartments for Rent in Chestnut Hill, MA with pricing that ranges from $1,200 to $12,500. There are also 506 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill ranging from $975 to $22,000.
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 $975 to $22,000 with an average monthly rent of $6,949.
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 $2,200 to $8,033, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,475 to $6,900. Four Bedroom Single-Family rentals are also available starting from $1,200 and Four Bedroom Apartments start at $1,400.
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

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!

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

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.

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Written by: Robin Stewart
Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.

Pet-Friendly Renting: Everything You Need to Know Before You Move
Written by: Christine Leonard, Esq.
For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.