
Luxury Homes for Rent in Chestnut Hill, MA (5,236 Rentals) Page 2 of 105
The most luxurious Homes in Chestnut Hill with high-end amenities, features, and finishes.


194 Gerry Rd

128 Thornton Rd

101 Independence Dr, Unit 1

213 Independence Dr

46 Gerry Rd

79 Thornton Rd, Unit 79

243 Gerry Rd

320 Hammond Pond Pky
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

1019 W Roxbury Pky, Unit 2

19 Sherman Rd

43 Independence Dr

101 Independence Dr

231 Gerry Rd

52 Independence Dr

39 Sherman Rd

52 Independence Dr

561 Vfw Pky

54 Independence Dr

164 Independence Dr

483 Vfw Pky

39 Sherman Rd

24 Thornton Rd

90 Thornton Rd

118 Independence Dr

108 Independence Dr

190 Gerry Rd

108 Independence Dr

105 Thornton Rd

201 Sherman Rd, Unit 810

65 Gerry Rd

37 Gerry Rd

495 Vfw Pky

36 Gerry Rd

128 Gerry Rd

26 Thornton Rd

133 Gerry Rd

214 Gerry Rd

148 Gerry Rd

31 Gerry Rd

5 Gerry Rd

116 Thornton Rd

245 Gerry Rd

107 Independence Dr

154 Independence Dr

74 Gerry Rd

102 Independence Dr

320 Hammond Pond Pky, Unit 203

11 Hammond Pond Pky, Unit 203

77 Sherman Rd
Chestnut Hill, 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 | $3,286 | $1,300 | $9,500 |
Chestnut Hill 3 Bedroom Homes for Rent | $3,979 | $1,280 | $10,000+ |
Chestnut Hill 4 Bedroom Homes for Rent | $4,775 | $950 | $10,000+ |
Chestnut Hill 5 Bedroom Homes for Rent | $5,983 | $1,025 | $10,000+ |
Chestnut Hill 6 Bedroom Homes for Rent | $7,154 | $975 | $10,000+ |
Chestnut Hill 7 Bedroom Homes for Rent | $3,287 | $1,000 | $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 7823 Apartments for Rent in Chestnut Hill, MA with pricing that ranges from $375 to $24,875. There are also 6054 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 $4,324.
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 $999 to $18,414, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,280 to $12,000. Four Bedroom Single-Family rentals are also available starting from $950 and Four Bedroom Apartments start at $1,150.
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.

The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Written by: Christine Leonard, Esq.
Hard truth. Moving is never easy. I’ve done it all – from local moves to cross-country relocations From packing to unpacking the last box, I have found moving to be an exhausting, expensive and stressful experience every time.

Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Written by: Christine Leonard, Esq.
Throughout the day, think about all the times that you have to pay for something. So many of us reach automatically for a credit card or even our phone for a quick payment.

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.