
Homes for Rent in Chestnut Hill, MA with Swimming Pool (180 Rentals)


20 Hammond Pond Pky, Unit 308

120 Thornton Rd

194 Gerry Rd

33 Gerry Rd

59 Thornton Rd

527 Vfw Pky
It's time to soak up some sun!
One of the easiest and more obvious ways of enjoying the summer sun is to lounge out by your community pool. Learn a Few Rules to Keep in Mind while at the pool.

29 Independence Dr

46 Gerry Rd

499 Vfw Pky

607 Vfw Pky

241 Gerry Rd

148 Independence Dr

250 Hammond Pond Pky, Unit 1203N

97 Sherman Rd

130 Sherman Rd, Unit 130

15 North Beacon St, Unit 212
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.

33 Westgate Rd, Unit 1

40 Broadlawn Dr

33 Westgate Rd, Unit 1

33 Westgate Rd, Unit 1

33 Westgate Rd

35 Westgate Rd, Unit 4

8 Bryon Rd

28 Bryon Rd, Unit 1

35 Westgate Rd, Unit 4

35 Westgate Rd, Unit 4

35 Westgate Rd

14 Bryon Rd, Unit 6

31 Westgate Rd, Unit 5
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.

50 Broadlawn Park, Unit 110

20 Westgate Rd, Unit #3

60 Broadlawn Park

589 Vfw Pky

162 Sherman Rd

45 Longwood Ave, Unit 403

45 Longwood Ave
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.

24 Juniper St, Unit 66

19 Winchester St, Unit 512

44 Washington St, Unit 517

33 Pond Ave, Unit 502

22 Chestnut Pl, Unit 311

22 Chestnut Pl, Unit 311

115 Marion St, Unit 414

77 Pond Ave, Unit 203

99 Pond Ave, Unit 407

1731 Beacon St, Unit 301

1731 Beacon St, Unit 301

1485 Beacon St, Unit 708
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

1731 Beacon St, Unit 422
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 | $3,260 | $2,000 | $8,400 |
Chestnut Hill 3 Bedroom Homes for Rent | $3,938 | $1,950 | $10,000+ |
Chestnut Hill 4 Bedroom Homes for Rent | $4,985 | $1,250 | $10,000+ |
Chestnut Hill 5 Bedroom Homes for Rent | $6,290 | $1,125 | $10,000+ |
Chestnut Hill 6 Bedroom Homes for Rent | $7,711 | $1,125 | $10,000+ |
Chestnut Hill 7 Bedroom Homes for Rent | $10,000 | $10,000 | $10,000+ |
Browse Top Homes for Rent in Chestnut Hill
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Chestnut Hill, 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 7778 Apartments for Rent in Chestnut Hill, MA with pricing that ranges from $900 to $50,000. There are also 6701 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestnut Hill ranging from $1,125 to $45,000.
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 $1,125 to $45,000 with an average monthly rent of $5,782.
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 $1,100 to $16,704, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,950 to $12,000. Four Bedroom Single-Family rentals are also available starting from $1,250 and Four Bedroom Apartments start at $975.
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 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.

The Freedom of Short-Term Leases: Exploring the Advantages for Renters
Written by: Bobbi Jackson
If you’re looking to relocate right now, a popular solution that may best fit your current rental needs is a short-term lease.