Cheap Homes for Rent in Cottage Hill Neighborhood of Winthrop, MA from $2,300 (27 Rentals)

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

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.

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property at 11 Walley St

11 Walley St

BostonMA02128

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.

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property at 25 Pratt St

25 Pratt St, Unit 1

25 Pratt St
BostonMA02134
property at 25 Pratt St

25 Pratt St, Unit 1

25 Pratt St
BostonMA02134
property at 7 Orient Ave

7 Orient Ave

BostonMA02128

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.

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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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Showing Results 1-27, Page 1 of 1

Cottage Hill, Winthrop, MA Local Guide

Cheapest Available Cottage Hill Apartments for Rent

 
Apartment ListingModel NameBed/BathPriced From
Broadway250A11BR,1BA$2,111

Best Value Apartments for Rent in Cottage Hill, MA

As of June 05, 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 25 Pratt St Model at 25 Pratt St, Unit 2 starting at $3,800 with a $0.38 price per square foot in the Cottage Hill 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
25 Pratt St, Unit 225 Pratt St3BR,1BA$0.38
720 Winthrop Ave, Unit #3720 Winthrop Ave2BR,1BA$0.26
76 Fremont St, Unit #276 Fremont St2BR,1BA$0.28
42 Ocean Ave, Unit 242 Ocean Ave2BR,1BA$0.30
271 Shirley St, Unit #2271 Shirley St2BR,1BA$0.42
65 Waldemar Ave, Unit #165 Waldemar Ave2BR,1BA$2.05
78 Temple Ave, Unit 178 Temple Ave2BR,1BA$2.10
1018 Shirley St, Unit #11018 Shirley St2BR,1.5BA$2.09
5 Hillside Ave, Unit #5A5 Hillside Ave2BR,2BA$2.09

Quick Rent Budget Calculator

How much rent can you afford?

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Frequently Asked Questions about Cottage Hill

What type of rentals are currently available in Cottage Hill?

There are currently 160 Apartments for Rent in Cottage Hill, MA with pricing that ranges from $900 to $5,600. There are also 71 Single Family Homes for rent, Condos, and Townhome rentals currently available in Cottage Hill ranging from $2,300 to $5,800.

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 $2,300 to $5,800 with an average monthly rent of $3,559.

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 $3,300 to $5,600, while Three Bedroom Homes, Condos, and Townhomes for rent range from $3,300 to $5,500. Four Bedroom Single-Family rentals are also available starting from $3,800 and Four Bedroom Apartments start at $2,850.

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.

decorative image for The 10 Best Affordable Neighborhoods in Boston, MA article

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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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.

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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.

decorative image for The Freedom of Short-Term Leases: Exploring the Advantages for Renters article

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.