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1 Bedroom Apartments Available NowFurnished Private Bedroom in East Boston
1059 Saratoga StBoston, MA 02128
Cheap Homes for Rent in Cottage Hill Neighborhood of Winthrop, MA from $1,500 (14 Rentals)
Search the lowest-cost Homes available for rent right now in the Cottage Hill area of Winthrop.
40 Cottage Park Rd
WinthropMA02152
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1 Bedroom Apartments Available Feb 11Furnished Bedroom with Private Bath in East Boston
1047 Saratoga StBoston, MA 02128
5 Irwin St
WinthropMA02152
85 Winthrop Shore Dr
WinthropMA02152
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Studio Apartments Available Now90 Winthrop Shore Dr
90 Winthrop Shore DrWinthrop, MA 02152
90 Winthrop Shore Dr, Unit 3
90 Winthrop Shore Dr
WinthropMA02152
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.
312 Shirley St
WinthropMA02152
312 Shirley St
WinthropMA02152
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$1,850
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Studio Apartments Available Now90 Winthrop Shore Dr
90 Winthrop Shore DrWinthrop, MA 02152
90 Winthrop Shore Dr, Unit 1-b 1-b U10
90 Winthrop Shore Dr
WinthropMA02152
34 Trident Ave
WinthropMA02152
435 Shirley St
WinthropMA02152
1030 Bennington St
BostonMA02128
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.
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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 | $2,907 | $2,600 | $3,350 |
| Cottage Hill 3 Bedroom Homes for Rent | $3,627 | $2,800 | $4,250 |
| Cottage Hill 4 Bedroom Homes for Rent | $3,950 | $3,800 | $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 14 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
- Nearby Winthrop neighborhoods
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Cheapest Available Cottage Hill Apartments for Rent
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| 87-90 Win | 0BR/1.0BA | Studio,1BA | $1,750 |
| Amaya | M1 | Studio,1BA | $2,350 |
Best Value Apartments for Rent in Cottage Hill, MA
As of January 07, 2026 the best value apartment in the Cottage Hill area is the $0.43 price per square foot 25 Pratt St Model at 25 Pratt St, Unit 2 in the in the Cottage Hill neighborhood starting from $4,250. The second greatest value Cottage Hill apartment is the 25 Pratt St Model at 25 Pratt St, Unit 1 starting at $2,400 with a $0.24 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. |
|---|---|---|---|
| 25 Pratt St, Unit 2 | 25 Pratt St | 4BR,2BA | $0.43 |
| 25 Pratt St, Unit 1 | 25 Pratt St | 1BR,1BA | $0.24 |
| 288 Pleasant St, Unit 1 | 288 Pleasant St | 2BR,1BA | $0.27 |
| 85 Gladstone St, Unit 3 | 85 Gladstone St | 3BR,1BA | $0.28 |
| 183 Cottage Park Rd, Unit 3 | 183 Cottage Park Rd | 4BR,2BA | $1.55 |
| 31 Faywood Ave, Unit 3 | 31 Faywood Ave | 4BR,2BA | $2.25 |
| 31 Faywood Ave, Unit 2 | 31 Faywood Ave | 4BR,2BA | $2.40 |
| 62 Locust St, Unit 1 | 62 Locust St | 3BR,1BA | $2.38 |
| 25 Pratt St, Unit 1 | 25 Pratt St | 1BR,1BA | $2.40 |
| 129 Bradstreet Ave, Unit 3 | 129 Bradstreet Ave | 1BR,1BA | $2.00 |
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.
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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 ArticleCash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.
Read ArticleQuick Rent Budget Calculator
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The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.
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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
3.0Pet 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 103 Apartments for Rent in Cottage Hill, MA with pricing that ranges from $1,500 to $4,250. There are also 46 Single Family Homes for rent, Condos, and Townhome rentals currently available in Cottage Hill ranging from $1,500 to $4,250.
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 $1,500 to $4,250 with an average monthly rent of $2,840.
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 $2,600 to $4,000, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,800 to $4,250. Four Bedroom Single-Family rentals are also available starting from $3,800 and Four Bedroom Apartments start at $3,400.
Expert Rental Resources
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
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How to Make Your Apartment Holiday-Ready: Renter-Friendly Tips
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Renting with Roommates: Realistic Expectations for Shared Lease
Written by: Christine Leonard, Esq.
Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.
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!