Cheap Apartments for Rent in the Cottage Hill Neighborhood of Winthrop, MA from $1,100 (28 Rentals)

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Search the lowest-cost Apartments available for rent right now in the Cottage Hill area of Winthrop.

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

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Waldemar Ave
2 Bedroom Apartments

Waldemar Ave

75 Waldemar AveEast Boston, MA 02128
  • Utilities Inc.
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Revere Bell Apartments
Studio to 2 Bedroom Apartments

Revere Bell Apartments

45-55 Belle Isle AveRevere, MA 02151
  • Utilities Inc.

Cottage Hill, Winthrop, MA Local Guide

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 ListingModel NameBed/BathPrice Per Sq.Ft.
25 Pratt St, Unit 225 Pratt St3BR,1BA$0.33
42 Ocean Ave, Unit 242 Ocean Ave2BR,1BA$0.30
25 Pratt St, Unit 125 Pratt St1BR,1BA$0.24
25 Pratt St, Unit 125 Pratt St1BR,1BA$0.24
25 Pratt St, Unit 225 Pratt St3BR,1BA$0.38
16 Franklin St, Unit A 16 Franklin St16 Franklin St2BR,1BA$1.92
78 Temple Ave, Unit 178 Temple Ave2BR,1BA$2.10
94 Terrace Ave, Unit #194 Terrace Ave1BR,1BA$2.04
95 Terrace Ave, Unit #195 Terrace Ave1BR,1BA$2.04
Atlas LoftsOne Bedroom1BR,1BA$2.23

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Pet Friendly Lifestyle
Cottage Hill, Winthrop, MA

Ranked #1

Among neighborhoods in Winthrop, MA for Apartment listings with Pet Friendly Amenities

Pet Friendliness Lifestyle Score

4.0
Pet Friendly

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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

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.

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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.

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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.

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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.

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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.