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$1,3001 Bedroom Apartments Available Jun 1
Furnished Private Bedroom in East Boston
1061 Saratoga StBoston, MA 02128
Cheap Homes for Rent in Cottage Hill Neighborhood of Winthrop, MA from $1,700 (14 Rentals)
Search the lowest-cost Homes available for rent right now in the Cottage Hill area of Winthrop.
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$1,5001 Bedroom Apartments Available May 1
Furnished Bedroom with Private Bath in East Boston
1047 Saratoga StBoston, MA 02128
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$1,5501 Bedroom Apartments Available Sep 1
Furnished Bedroom with Private Bath in East Boston
1047 Saratoga StBoston, MA 02128
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$1,650Studio Apartments Available Now
90 Winthrop Shore Dr
90 Winthrop Shore DrWinthrop, MA 02152
90 Winthrop Shore Dr
WinthropMA02152
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$1,750Studio Apartments Available Apr 1
90 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
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$1,800Studio Apartments Available Now
312 Shirley St
312 Shirley StWinthrop, MA 02152
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$2,000Studio Apartments Available Now
312 Shirley St
312 Shirley StWinthrop, MA 02152
800 Governors Dr
WinthropMA02152
25 Pratt St
BostonMA02134
214 Bradstreet Ave, Unit 2
214 Bradstreet Ave
RevereMA02151
900 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.
Showing Results 1-14, 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 | $2,738 | $2,025 | $3,200 |
| Cottage Hill 3 Bedroom Homes for Rent | $3,314 | $2,700 | $4,200 |
| Cottage Hill 4 Bedroom Homes for Rent | $4,037 | $3,650 | $4,500 |
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
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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 | $1,650 |
| Amaya | M1 | Studio,1BA | $2,030 |
Best Value Apartments for Rent in Cottage Hill, MA
As of March 12, 2026 the best value apartment in the Cottage Hill area is the $1.55 price per square foot 183 Cottage Park Rd Model at 183 Cottage Park Rd, Unit 3 in the in the Beachmont neighborhood starting from $3,400. The second greatest value Cottage Hill apartment is the 31 Faywood Ave Model at 31 Faywood Ave, Unit 3 starting at $3,600 with a $2.25 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. |
|---|---|---|---|
| 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 |
| 953 Shirley St, Unit 2 | 953 Shirley St | 3BR,1BA | $3.08 |
| 44 Ashley St | 44 Ashley St | 4BR,2BA | $3.17 |
| 135 Bellingham Ave, Unit 1 | 135 Bellingham Ave | 3BR,1BA | $2.08 |
| 21 Prescott St, Unit 1 | 21 Prescott St | 2BR,1BA | $2.18 |
| 25 Pratt St, Unit 1 | 25 Pratt St | 1BR,1BA | $2.40 |
| 82 Gladstone St, Unit 2 | 82 Gladstone St | 2BR,1BA | $3.15 |
| 81 Gladstone St, Unit 2 | 81 Gladstone St | 2BR,1BA | $3.04 |
| 82 Gladstone St, Unit 2 | 82 Gladstone St | 2BR,1BA | $3.04 |
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
3.5Pet Friendly
Best Local Schools in Cottage Hill, Winthrop, MA
Arthur T. Cummings Elementary School
Winthrop School District
Public School - Grades 3-5 (466)
5 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 109 Apartments for Rent in Cottage Hill, MA with pricing that ranges from $1,300 to $6,777. There are also 49 Single Family Homes for rent, Condos, and Townhome rentals currently available in Cottage Hill ranging from $1,700 to $4,500.
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 $1,700 to $4,500 with an average monthly rent of $2,864.
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 $2,500 to $6,777, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,700 to $4,200. Four Bedroom Single-Family rentals are also available starting from $3,650 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.
Helpful Local Expert Guides
The 10 Best Affordable Neighborhoods in Boston, MA
Written by: Amelia Ramstead
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A Local Experts Guide to the Top Boston Neighborhoods for College Renters
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Hi! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, Massachusetts! We’re excited to help you find your new home, and getting to know the neighborhood is an important part of that process!
Explore Like a Local: The Insider's Guide to Boston
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Hello from Boston, Massachusetts! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, and I’m here to give you the inside scoop on this unique city.
Boston Major Employer Neighborhood Guide: Living Near UMass, MGH, & State Street
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Hi! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, Massachusetts. Getting to know your new neighborhood is one of the best parts of moving, and we’re excited to help you get started.
Articles, How-To's, and Tips
Maximizing Your Refund: Essential Tax Tips for Renters
Written by: Christine Leonard, Esq.
Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.
18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Written by: Lauren Harrington
Renting your next home can feel thrilling and overwhelming at the same time.
A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment
Written by: Bob Mallory
Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.
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.