
Cheap Homes for Rent in Cottage Hill Neighborhood of Winthrop, MA from $1,900 (17 Rentals)
Search the lowest-cost Homes available for rent right now in the Cottage Hill area of Winthrop.


312 Shirley St

312 Shirley St

900 Governors Dr

400 Governors Dr

25 Pratt St, Unit 1

25 Pratt St, Unit 1

25 Pratt St, Unit 1

352 Shirley St

352 Shirley St
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

7 Walley St, Unit 106

11 Walley St

59 Cottage Park Rd

720 Winthrop Ave, Unit 3

50 Edgehill Rd

100 Governors Dr

23 Tafts Ave
Cottage Hill, Winthrop, MA Local Guide

How much does it cost to rent a home in Cottage Hill?
Bedroom | Average Rent | Cheapest Rent | Highest Rent |
---|---|---|---|
Cottage Hill 2 Bedroom Homes for Rent | $2,843 | $2,100 | $4,000 |
Cottage Hill 3 Bedroom Homes for Rent | $3,445 | $3,000 | $4,000 |
Cottage Hill 4 Bedroom Homes for Rent | $4,233 | $3,900 | $5,200 |
Browse Homes for Rent in this Neighborhood
There are currently 17 rentals with your search options within a 2 mile radius of the Cottage Hill Neighborhood of Winthrop, MA.
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Cottage Hill, Winthrop, MA Local Guide
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Best Value Apartments for Rent in Cottage Hill, MA
As of April 10, 2025 the best value apartment in the Cottage Hill area is the $0.33 price per square foot 25 Pratt St Model at 25 Pratt St, Unit 2 in the in the Cottage Hill neighborhood starting from $3,300. The second greatest value Cottage Hill apartment is the 42 Ocean Ave Model at 42 Ocean Ave, Unit 2 starting at $2,950 with a $0.30 price per square foot in the Beachmont neighborhood. Here is today’s list of the best values for Cottage Hill apartments based on price per square foot:
Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
---|---|---|---|
25 Pratt St, Unit 2 | 25 Pratt St | 3BR,1BA | $0.33 |
42 Ocean Ave, Unit 2 | 42 Ocean Ave | 2BR,1BA | $0.30 |
720 Winthrop Ave, Unit #3 | 720 Winthrop Ave | 2BR,1BA | $0.26 |
25 Pratt St, Unit 2 | 25 Pratt St | 3BR,1BA | $0.38 |
25 Pratt St, Unit 1 | 25 Pratt St | 1BR,1BA | $0.24 |
58 Lewis Ave, Unit #302 | 58 Lewis Ave | 1BR,1BA | $0.26 |
271 Shirley St, Unit #2 | 271 Shirley St | 2BR,1BA | $0.42 |
82 Temple Ave, Unit #1 | 82 Temple Ave | 1BR,1BA | $1.15 |
16 Franklin St, Unit A 16 Franklin St | 16 Franklin St | 2BR,1BA | $1.92 |
17 Waldemar Ave, Unit #301 | 17 Waldemar Ave | 2BR,1BA | $2.00 |
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Frequently Asked Questions about Cottage Hill
What type of rentals are currently available in Cottage Hill?
There are currently 196 Apartments for Rent in Cottage Hill, MA with pricing that ranges from $1,080 to $5,614. There are also 64 Single Family Homes for rent, Condos, and Townhome rentals currently available in Cottage Hill ranging from $1,900 to $5,200.
What is the current price range for Rental Homes in Cottage Hill?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Cottage Hill ranges from $1,900 to $5,200 with an average monthly rent of $2,994.
How much are larger Three and Four Bedroom Rentals in Cottage Hill?
For those who are looking for larger living arrangements, Three Bedroom Apartments in Cottage Hill range from $3,000 to $5,614, while Three Bedroom Homes, Condos, and Townhomes for rent range from $3,000 to $4,000. Four Bedroom Single-Family rentals are also available starting from $3,900 and Four Bedroom Apartments start at $4,000.
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.

Understanding Amenity Fees: Know Where You Might Be Able to Save Money
Written by: Amber Kanuckel
With the rising costs of housing, a lot of renters are asking this question: Is it possible to opt out of various amenities that your rental property offers so that you can avoid paying the fees.

Renting Smart: Lease Basics Every Renter Needs
Written by: Christine Leonard, Esq.
Often, in the excitement of finding a new place to live, there’s a rush to make it happen, and - too often - a new tenant signs a lease without reading it carefully.

Battling the Butts: Your Guide to the Reality of Smoke-Free Renting
Written by: Andrea Lee Negroni, JD
While many apartment buildings are “no smoking” properties, it’s hard to know exactly how many. In 2017, the National Apartment Association reported more than half of rental properties had smoke free policies.