
Luxury Homes for Rent in Cottage Hill Neighborhood of Winthrop, MA (31 Rentals)
The most luxurious Homes in the Cottage Hill area of Winthrop with high-end amenities, features, and finishes.


92 Winthrop Shore Dr, Unit 2

76 Fremont St, Unit 3

5 Fremont St, Unit 106

90 Winthrop Shore Dr

6 Edgehill Rd

45 Pleasant St
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.

1 Seal Harbor Rd

249 Winthrop Shore Dr

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
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.

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

1 Orient Ave, Unit 3C

44 Ashley St, Unit 4-bed2bath
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.

90 Gladstone St, Unit 1

89 Gladstone St

Total Monthly Price
1008 Winthrop Ave

72 Orient Ave

972 Saratoga St

82 Gladstone St

890 Winthrop Ave
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

11 Walley St

57 Bellingham Ave

25 Teragram St
Cottage Hill, Winthrop, MA Local Guide

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 | $2,874 | $2,600 | $3,200 |
| Cottage Hill 3 Bedroom Homes for Rent | $4,035 | $2,800 | $6,500 |
| Cottage Hill 4 Bedroom Homes for Rent | $3,900 | $3,800 | $4,200 |
Browse Homes for Rent in this Neighborhood
There are currently 31 rentals with your search options within a 2 mile radius of the Cottage Hill Neighborhood of Winthrop, MA.
Explore Winthrop
Frequently Asked Questions about Cottage Hill
What type of rentals are currently available in Cottage Hill?
There are currently 110 Apartments for Rent in Cottage Hill, MA with pricing that ranges from $1,175 to $4,250. There are also 44 Single Family Homes for rent, Condos, and Townhome rentals currently available in Cottage Hill ranging from $1,595 to $6,500.
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 $1,595 to $6,500 with an average monthly rent of $2,924.
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 $4,200, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,800 to $6,500. 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.
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

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.

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!