
Pet Friendly Homes for Rent in Winchester, MA (196 Rentals)
Homes for rent in Winchester that love your dogs or cats as much as you do!


2 George Rd

67 Church St

171 Swanton St

23 Jefferson Rd

34 Glen Rd

3 Wood Ln

120 Jerome St

220 Massachusetts Ave, Unit 3
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.

25 Arlington Rd, Unit 3

12 Water St, Unit 1

37 Westminster Ave, Unit 2

26 Leonard St

132 Broadway, Unit 1

104 Forest St

104 Forest St, Unit 104

104 Forest St

116 Medford St, Unit 1

47 Webster St, Unit 47
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.

2012 Symmes Cir, Unit 1

86 Coolidge Rd

35 Bowdoin St, Unit 35

41 Rublee St

29 Addison St

8 Farmer Cir

6 Farmer Cir

6 Farmer Cir

37 Oldham Rd

422 High St, Unit 10
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.

64 Salem St, Unit 02

9 Circuit St, Unit 1

26 Bradlee Rd

20 Burget Ave

81 College Ave, Unit 2

260 Boston Ave, Unit 1

258 Boston Ave, Unit 3

227 Boston Ave, Unit 1

7 Greenleaf Ave, Unit 1

49 Adams St, Unit 49

12 Bellevue St, Unit 1
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

119 Burget Ave, Unit 2

10 Greenleaf Ave

217 Arlington

14 Woodbine Rd

33 Lincoln St, Unit 31-1

14 Woodbine Rd

14 Woodbine Rd

476 Fulton St, Unit 476

476 Fulton St

477 Fulton St
Winchester, MA Local Guide

How much does it cost to rent a home in Winchester?
Bedroom | Average Rent | Cheapest Rent | Highest Rent |
---|---|---|---|
Winchester 2 Bedroom Homes for Rent | $3,151 | $2,350 | $6,400 |
Winchester 3 Bedroom Homes for Rent | $3,852 | $2,000 | $6,550 |
Winchester 4 Bedroom Homes for Rent | $5,002 | $3,425 | $7,700 |
Winchester 5 Bedroom Homes for Rent | $6,506 | $4,225 | $10,000+ |
Winchester 6 Bedroom Homes for Rent | $7,889 | $5,945 | $10,000+ |
Winchester 7 Bedroom Homes for Rent | $8,497 | $6,995 | $10,000+ |
Browse Top Homes for Rent in Winchester
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Winchester, MA Local Guide
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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 Winchester
What type of rentals are currently available in Winchester?
There are currently 803 Apartments for Rent in Winchester, MA with pricing that ranges from $955 to $10,400. There are also 508 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,650 to $40,000.
What is the current price range for Rental Homes in Winchester?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Winchester ranges from $1,650 to $40,000 with an average monthly rent of $4,894.
How much are larger Three and Four Bedroom Rentals in Winchester?
For those who are looking for larger living arrangements, Three Bedroom Apartments in Winchester range from $2,850 to $7,500, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,000 to $6,550. Four Bedroom Single-Family rentals are also available starting from $3,425 and Four Bedroom Apartments start at $3,200.
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.