
Luxury Apartments for Rent in the Cottage Hill Neighborhood of Winthrop, MA (68 Rentals)
The most luxurious Apartments in the Cottage Hill area of Winthrop with high-end amenities, features, and finishes.


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63 Upland Rd, Unit 1

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439 Winthrop St, Unit 1

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62 Locust St, Unit 1

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288 Pleasant St, Unit 1

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183 Cottage Park Rd, Unit 3

439 Winthrop St, Unit 1

92 Winthrop Shore Dr, Unit 2

76 Fremont St, Unit 3

5 Fremont St, Unit 106
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.

175 Somerset Ave

90 Winthrop Shore Dr

14 Beach Rd

73 Grovers Ave

14 Perkins St

49R Siren St

11 Forrest St

25 Seafoam Ave

10 Charles St
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.

117 Winthrop Shore Dr

5 Fremont St

31-33-33 Pleasant Park Rd

19 Beach Rd

45 Pleasant St

1 Seal Harbor Rd

249 Winthrop Shore Dr

29 Dolphin Ave

40 Cottage Park Rd
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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Amaya

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31 Faywood Ave, Unit 2

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1021 Winthrop Ave, Unit #2

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85 Gladstone St, Unit 3

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120 Gladstone St, Unit #3

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1110 Saratoga St, Unit 1

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44 Ashley St

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25 Pratt St, Unit 2

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31 Faywood Ave, Unit 3

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202 Orient Ave, Unit 2
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

15 Walley St, Unit 206

1030 Bennington St, Unit 5

1030 Bennington St, Unit 5

1030 Bennington St, Unit 5

1030 Bennington St, Unit 5

82 Gladstone St, Unit 2

184 Gladstone St, Unit 1

184 Gladstone St, Unit 1

25 Pratt St, Unit 2

215 Leyden St, Unit 1
Cottage Hill, Winthrop, MA Local Guide

How much does it cost to rent an apartment in Cottage Hill?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Cottage Hill Studio Apartments | $2,623 | $1,695 | $2,930 |
| Cottage Hill 1 Bedroom Apartments | $3,015 | $1,500 | $3,775 |
| Cottage Hill 2 Bedroom Apartments | $2,982 | $2,400 | $4,075 |
| Cottage Hill 3 Bedroom Apartments | $3,174 | $2,600 | $5,000 |
| Cottage Hill 4 Bedroom Apartments | $3,840 | $3,400 | $4,250 |
Browse Apartments in this Neighborhood
There are currently 68 rentals with your search options within a 2 mile radius of the Cottage Hill Neighborhood of Winthrop, MA.
See all Apartments in WinthropExplore Winthrop
Cottage Hill, Winthrop, MA Local Guide
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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 ArticleThe 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
How much rent can you afford?
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.
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
School data provided by Great Schools
Frequently Asked Questions about Cottage Hill
How much are Studio apartments in Cottage Hill?
There are currently 27 Studio Apartments in Cottage Hill with rent ranges from $1,695 to $2,930 with an average price of $2,623.
What is the current price range for One Bedroom Cottage Hill Apartments for rent?
Today's rental pricing for One Bedroom Apartments in Cottage Hill ranges from $1,500 to $3,775 with an average monthly rent of $3,015.
What does renting a Two Bedroom Apartment in Cottage Hill cost?
The monthly rent prices of Two Bedroom Apartments currently available in Cottage Hill range from $2,400 to $4,075. Today's average rental price for Two Bedrooms here is $2,982.
How expensive are Cottage Hill Three Bedroom Apartments?
There are currently 17 Three Bedroom Apartments listings available in Cottage Hill on ApartmentHomeLiving.com. The pricing ranges from $2,600 to $5,000 - averaging $3,174 for the location.
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
Boston is known for its exciting combination of early American history and modern high-tech universities and employers.

A Local Experts Guide to the Top Boston Neighborhoods for College Renters
Written by: Amelia Ramstead
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
Written by: Amelia Ramstead
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
Written by: Amelia Ramstead
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

How to Make Your Apartment Holiday-Ready: Renter-Friendly Tips
Written by: Justin Habersaat
Getting your apartment ready for the holidays can be exciting but sometimes challenging in a smaller space. Here are some modern tips to keep things festive, safe, and inviting this season.

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!

