Cheap Apartments for Rent in the Cottage Hill Neighborhood of Winthrop, MA from $1,100 (28 Rentals)
Search the lowest-cost Apartments available for rent right now in the Cottage Hill area of Winthrop.

70 Beach Rd

87 Winthrop Shore Dr

85 Winthrop Shore Dr, Unit 8

76 Sunnyside Ave, Unit 3

34 Trident Ave

12 Harvard St

267 Washington Ave, Unit #3A

312 Shirley St, Unit #200

265 Washington Ave, Unit #3A

205 Winthrop St, Unit #8
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

203 Winthrop Shore Dr, Unit #8

Furnished Private Bedroom in East Boston

Furnished Private Bedroom in East Boston

1061 Saratoga St

1047 Saratoga St

Ocean Point Apartments

85 Bennington St, Unit #3

1048 Bennington St, Unit #3

1046 Bennington St, Unit #3
Cottage Hill, Winthrop, MA Local Guide

How much does it cost to rent an apartment in Cottage Hill?
Bedroom | Average Rent | Cheapest Rent | Highest Rent |
---|---|---|---|
Cottage Hill Studio Apartments | $2,527 | $1,650 | $2,850 |
Cottage Hill 1 Bedroom Apartments | $2,722 | $1,175 | $3,825 |
Cottage Hill 2 Bedroom Apartments | $3,307 | $2,300 | $4,740 |
Cottage Hill 3 Bedroom Apartments | $3,703 | $3,000 | $5,614 |
Cottage Hill 4 Bedroom Apartments | $4,342 | $4,000 | $5,595 |
Browse Apartments in this Neighborhood
There are currently 28 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 March 14, 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 |
25 Pratt St, Unit 1 | 25 Pratt St | 1BR,1BA | $0.24 |
25 Pratt St, Unit 1 | 25 Pratt St | 1BR,1BA | $0.24 |
25 Pratt St, Unit 2 | 25 Pratt St | 3BR,1BA | $0.38 |
16 Franklin St, Unit A 16 Franklin St | 16 Franklin St | 2BR,1BA | $1.92 |
78 Temple Ave, Unit 1 | 78 Temple Ave | 2BR,1BA | $2.10 |
94 Terrace Ave, Unit #1 | 94 Terrace Ave | 1BR,1BA | $2.04 |
95 Terrace Ave, Unit #1 | 95 Terrace Ave | 1BR,1BA | $2.04 |
Atlas Lofts | One Bedroom | 1BR,1BA | $2.23 |
Quick Rent Budget Calculator
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Pet Friendly LifestyleCottage Hill, Winthrop, MA
Ranked #1
Among neighborhoods in Winthrop, MA for Apartment listings with Pet Friendly Amenities
Pet Friendliness Lifestyle Score
4.0Pet Friendly
Best Local Schools in Cottage Hill, Winthrop, MA
Arthur T. Cummings Elementary School
School data provided by Great Schools
Best Local Schools in Cottage Hill, Winthrop, MA
Arthur T. Cummings Elementary School
School data provided by Great Schools
Getting Around the Cottage Hill Neighborhood in Winthrop, MA
Walk Score®
62 / 100
Somewhat Walkable
Some errands can be accomplished on foot
Bike Score®
35 / 100
Somewhat Bikeable
Minimal bike infrastructure
What Are Walk Score®, Transit Score®, and Bike Score® Ratings?
- Walk Score® measures the walkability of any address.
- Transit Score® measures access to public transit.
- Bike Score® measures the bikeability of any address.
Frequently Asked Questions about Cheap Cottage Hill Apartments
What is the Cheapest Studio apartment in Cottage Hill?
Currently the most affordable Cheap Studio Apartment in Cottage Hill is at DUO listed at $2,263.
How much is rent for a Cheap One Bedroom Cottage Hill Apartment?
The lowest price for a Cheap One Bedroom Cottage Hill Apartment is $2,225 at Atlas Lofts.
What is the lowest price for a Cheap Two Bedroom Cottage Hill Apartment for rent?
Today's best deal for a Cheap Two Bedroom Apartment in Cottage Hill is starting from $2,750 at 87-90 Win.
What is the most affordable Cottage Hill Three Bedroom Apartment?
The best deal on a cheap Cottage Hill Three Bedroom Apartment rental is at Parkside Commons Apartments and starts from $3,762.
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.

What to Know About Fees and Fines When Renting
Written by: Trey Huguley
When it comes to renting a new apartment or home there can be a number of fees that you will want to keep in mind going into the process.

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.