
Luxury Homes for Rent in Cottage Hill Neighborhood of Winthrop, MA (57 Rentals)
The most luxurious Homes in the Cottage Hill area of Winthrop with high-end amenities, features, and finishes.


152 Pleasant St

5 Fremont St, Unit 106

87 Winthrop Shore Dr, Unit uni5 2-bed 1-bath

90 Winthrop Shore Dr, Unit uni2 2-bed

92 Winthrop Shore Dr, Unit 2
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.

1079 Shirley St

49 Bates Ave

62 Park Ave

15 Ocean Ave

28 Trident Ave

141 Grovers Ave

90 Gladstone St

90 Gladstone St, Unit 1

90 Gladstone St, Unit 1

1 Orient Ave, Unit 3

44 Ashley St, Unit 4-bed2bath
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.

2 Walley St, Unit 1

215 Leyden St, Unit 1

25 Pratt St, Unit 2

16 Boardman St, Unit 303

8 Ford St

14 Leverett Ave, Unit 1

184 Gladstone St
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.

14 Leverett Ave

184 Gladstone St, Unit 1

184 Gladstone St, Unit Gladstone St

184 Gladstone St, Unit 1

184 Gladstone St, Unit 1

103 Barnes Ave

1030 Bennington St, Unit 5

1030 Bennington St, Unit 5

1030 Bennington St, Unit 5

1030 Bennington St, Unit 5

1030 Bennington St

1030 Bennington St, Unit 5
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

1030 Bennington St

1030 Bennington St, Unit 5

1030 Bennington St, Unit 5

7 Orient Ave

15 Walley St, Unit 206
Cottage Hill, Winthrop, MA Local Guide

How much does it cost to rent a home in Cottage Hill?
Bedroom | Average Rent | Cheapest Rent | Highest Rent |
---|---|---|---|
Cottage Hill 2 Bedroom Homes for Rent | $2,988 | $2,600 | $3,800 |
Cottage Hill 3 Bedroom Homes for Rent | $3,803 | $3,300 | $5,500 |
Cottage Hill 4 Bedroom Homes for Rent | $4,028 | $3,800 | $4,200 |
Cottage Hill 5 Bedroom Homes for Rent | $4,325 | $2,850 | $5,800 |
Browse Homes for Rent in this Neighborhood
There are currently 57 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
- Nearby Cities
- ZIP codes
- Local Counties
- School Districts
Quick 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.
Frequently Asked Questions about Cottage Hill
What type of rentals are currently available in Cottage Hill?
There are currently 159 Apartments for Rent in Cottage Hill, MA with pricing that ranges from $900 to $5,600. There are also 71 Single Family Homes for rent, Condos, and Townhome rentals currently available in Cottage Hill ranging from $2,300 to $5,800.
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 $2,300 to $5,800 with an average monthly rent of $3,509.
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 $3,300 to $5,600, while Three Bedroom Homes, Condos, and Townhomes for rent range from $3,300 to $5,500. Four Bedroom Single-Family rentals are also available starting from $3,800 and Four Bedroom Apartments start at $2,850.
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.

The Art of the Rental Viewing: What to look for during a property tour
Written by: Marie Brown
You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.

Know Your Budget: Calculating What You Can Realistically Afford When Renting
Written by: Lauren Harrington
Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.

The Freedom of Short-Term Leases: Exploring the Advantages for Renters
Written by: Bobbi Jackson
If you’re looking to relocate right now, a popular solution that may best fit your current rental needs is a short-term lease.