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$2,600
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Jan 1, 2026Total Monthly Price
Base Rent
$2,600
Total Monthly Price
$2,600
439 Winthrop St, Unit 1
439 Winthrop StWinthrop, MA 02152
Pet Friendly Apartments for Rent in the Cottage Hill Neighborhood of Winthrop, MA (31 Rentals)
Apartments for rent in the Cottage Hill area of Winthrop that love your dogs or cats as much as you do!
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$1,850
Total Monthly Price12 Month Lease Term
Studio Apartment Available NowTotal Monthly Price
Base Rent
$1,850
Total Monthly Price
$1,850
95 Bowdoin St, Unit 3
95 Bowdoin StWinthrop, MA 02152
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$1,800
Total Monthly Price12 Month Lease Term
Studio Apartment Available NowTotal Monthly Price
Base Rent
$1,800
Total Monthly Price
$1,800
98 Winthrop Shore Dr
98 Winthrop Shore DrWinthrop, MA 02152
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$4,995
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,995
Total Monthly Price
$4,995
176 Winthrop Shore Dr, Unit 1
176 Winthrop Shore DrWinthrop, MA 02152
85 Winthrop Shore Dr
WinthropMA02152
90 Winthrop Shore Dr, Unit 1-b 1-b U10
90 Winthrop Shore Dr
WinthropMA02152
439 Winthrop St, Unit 1
439 Winthrop St
WinthropMA02152
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.
92 Winthrop Shore Dr, Unit 2
92 Winthrop Shore Dr
WinthropMA02152
5 Fremont St, Unit 106
5 Fremont St
WinthropMA02152
141 Grovers Ave
WinthropMA02152
312 Shirley St
WinthropMA02152
435 Shirley St
WinthropMA02152
5 Irwin St
WinthropMA02152
34 Trident Ave
WinthropMA02152
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.
249 Winthrop Shore Dr
WinthropMA02152
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Rent Specials
$2,265 - $4,075
Total Monthly Price
Studio to 2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$2,265 - $4,075
Total Monthly Price
$2,265 - $4,075
Amaya
50 Salt StRevere, MA 02151
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$2,400
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available Aug 31, 2026Total Monthly Price
Base Rent
$2,400
Total Monthly Price
$2,400
25 Pratt St, Unit 1
25 Pratt StBoston, MA 02134
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$2,750
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Feb 1, 2026Total Monthly Price
Base Rent
$2,750
Total Monthly Price
$2,750
202 Orient Ave, Unit 2
202 Orient AveBoston, MA 02128
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.
15 Walley St, Unit 206
15 Walley St
BostonMA02128
25 Pratt St, Unit 2
25 Pratt St
BostonMA02134
44 Ashley St, Unit 4-bed2bath
44 Ashley St
BostonMA02128
1 Orient Ave, Unit 3C
1 Orient Ave
BostonMA02128
90 Gladstone St, Unit 1
90 Gladstone St
BostonMA02128
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$3,500
Total Monthly Price
3 Bedroom Apartments Available Dec 30Total Monthly Price
Base Rent
$3,030
Required Monthly Fees
$470
Total Monthly Price
$3,500
1008 Winthrop Ave
1008 Winthrop AveRevere, MA 02151
25 Teragram St
BostonMA02128
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
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Showing Results 1-31, 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 an apartment in Cottage Hill?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Cottage Hill Studio Apartments | $2,614 | $1,695 | $2,930 |
| Cottage Hill 1 Bedroom Apartments | $2,974 | $1,250 | $3,775 |
| Cottage Hill 2 Bedroom Apartments | $2,985 | $2,200 | $4,075 |
| Cottage Hill 3 Bedroom Apartments | $3,237 | $2,600 | $4,995 |
| Cottage Hill 4 Bedroom Apartments | $3,827 | $3,300 | $4,250 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Apartments 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.
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Cottage Hill, Winthrop, MA Local Guide
- Nearby Winthrop neighborhoods
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Cheapest Pet Friendly Apartment Rentals in Cottage Hill
| Apartment Listing | Model Name | Priced From |
|---|---|---|
| Amaya | M1 | $2,350 |
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
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.
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If you’re an expert on all things Cottage Hill, tell us what you love (and don't) by rating it and writing a review.
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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
4.0Pet 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 Pet Friendly Cottage Hill Apartments
What is the Cheapest Pet Friendly apartment in Cottage Hill?
Currently the most affordable Pet Friendly Apartment in Cottage Hill is at 98 Winthrop Shore Dr listed at $1,800.
How much is the average rent for a Pet Friendly Cottage Hill Apartment?
The average rent for a Pet Friendly Apartment in Cottage Hill is $3,343.
What is the largest Pet Friendly Cottage Hill Apartment for rent?
Today's Pet Friendly apartment with the most square footage in Cottage Hill is a 1,500 square feet unit starting from $4,995 at 176 Winthrop Shore Dr, Unit 1.
What is the average size for Cottage Hill Pet Friendly Apartments for rent?
The average size for a Pet Friendly rental in Cottage Hill is currently at 949 sq ft.
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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Everything is a negotiation in real estate!