85 Winthrop Shore Dr
WinthropMA02152
Cheap Homes for Rent in Cottage Hill Neighborhood of Winthrop, MA from $1,600 (9 Rentals)
Search the lowest-cost Homes available for rent right now in the Cottage Hill area of Winthrop.
90 Winthrop Shore Dr, Unit 1-b 1-b U10
90 Winthrop Shore Dr
WinthropMA02152
34 Trident Ave
WinthropMA02152
1030 Bennington St, Unit 15
1030 Bennington St
BostonMA02128
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.
1062 Saratoga St, Unit 3
1062 Saratoga St
BostonMA02128
15 Walley St, Unit 206
15 Walley St
BostonMA02128
352 Shirley St
WinthropMA02152
1000 Governors Dr
WinthropMA02152
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.
439 Winthrop St, Unit 1
439 Winthrop St
WinthropMA02152
Showing Results 1-9, Page 1 of 1
Cottage Hill, Winthrop, MA Local Guide
View of Winthrop, Massachusetts from the northeast by Sean 2015 is licensed under Internal
How much does it cost to rent a home in Cottage Hill?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Cottage Hill 2 Bedroom Homes for Rent | $2,846 | $2,600 | $3,300 |
| Cottage Hill 3 Bedroom Homes for Rent | $3,990 | $2,500 | $5,500 |
| Cottage Hill 4 Bedroom Homes for Rent | $3,800 | $3,400 | $4,200 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Homes for Rent in this Neighborhood
There are currently 9 rentals with your search options within a 2 mile radius of the Cottage Hill Neighborhood of Winthrop, MA.
Explore Winthrop
Cottage Hill, Winthrop, MA Local Guide
- Nearby Winthrop neighborhoods
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Cheapest Available Cottage Hill Apartments for Rent
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Amaya | M1 | Studio,1BA | $2,430 |
Best Value Apartments for Rent in Cottage Hill, MA
As of November 25, 2025 the best value apartment in the Cottage Hill area is the $0.27 price per square foot 288 Pleasant St Model at 288 Pleasant St, Unit 1 in the in the Beachmont neighborhood starting from $2,650. The second greatest value Cottage Hill apartment is the 25 Pratt St Model at 25 Pratt St, Unit 2 starting at $4,250 with a $0.43 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 Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| 288 Pleasant St, Unit 1 | 288 Pleasant St | 2BR,1BA | $0.27 |
| 25 Pratt St, Unit 2 | 25 Pratt St | 4BR,2BA | $0.43 |
| 71 Wilshire St, Unit 2 | 71 Wilshire St | 3BR,1BA | $0.37 |
| 183 Cottage Park Rd, Unit 3 | 183 Cottage Park Rd | 4BR,2BA | $1.55 |
| 1148 Bennington St, Unit 1 | 1148 Bennington St | 4BR,2BA | $1.93 |
| 31 Faywood Ave, Unit 3 | 31 Faywood Ave | 4BR,2BA | $2.25 |
| 21 Seafoam Ave, Unit 3 | 21 Seafoam Ave | 4BR,2BA | $2.13 |
| 354 Shirley St, Unit 3 | 354 Shirley St | 3BR,1BA | $2.04 |
| 3 Orchard St, Unit #3 | 3 Orchard St | 2BR,1BA | $2.70 |
| 25 Pratt St, Unit 1 | 25 Pratt St | 1BR,1BA | $2.40 |
Don't Settle: How to Negotiate Your Apartment Lease and Save Money
Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.
Read Article
The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.
Read ArticleQuick Rent Budget Calculator
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Pet Friendly LifestyleCottage Hill, Winthrop, MA
Ranked #2
Among cities in Massachusetts for Apartment listings with Pet Friendly Amenities.
Pet Friendliness Lifestyle Score
3.5Pet Friendly
Best Local Schools in Cottage Hill, Winthrop, MA
Arthur T. Cummings Elementary School
Winthrop School District
Public School - Grades 3-5 (431)
6 out of 10
School data provided by Great Schools
Frequently Asked Questions about Cottage Hill
What type of rentals are currently available in Cottage Hill?
There are currently 114 Apartments for Rent in Cottage Hill, MA with pricing that ranges from $1,270 to $4,995. There are also 46 Single Family Homes for rent, Condos, and Townhome rentals currently available in Cottage Hill ranging from $1,650 to $5,500.
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 $1,650 to $5,500 with an average monthly rent of $2,875.
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 $2,450 to $4,995, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,500 to $5,500. Four Bedroom Single-Family rentals are also available starting from $3,400 and Four Bedroom Apartments start at $3,200.
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.
Apartment Common Area Rules: What Renters Need to Know
Written by: Christine Leonard, Esq.
Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.
How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!
The Rental Move-In Inspection Checklist: A Guide for Renters
Written by: Trey Huguley
The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.