
Pet Friendly Homes for Rent in Winchester, MA (229 Rentals)
Homes for rent in Winchester that love your dogs or cats as much as you do!


270 Cross St

148 Forest St

12 Olde Village Dr

115 Washington St

39 Loring Ave

270 Cross St

186 Ridge St

14 Brattle Ln, Unit 35

14 Dudley St, Unit 6

11 Allen St, Unit 3
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

49 Broadway, Unit #6

211 Forest St, Unit 1

20 Hamilton Rd, Unit 201

3 Acton St, Unit 1

27 Highland Ave, Unit 2

43 Surry Rd, Unit 43

12 Water St, Unit 1

1051 Massachusetts Ave, Unit 3

78 Warren St, Unit 1

68 Central St

24 Cleveland St, Unit 1

378 Massachusetts Ave, Unit 2

132 Rawson Rd, Unit 132

3 Ortona St

34 Fessenden Rd, Unit 34

18 Pine St, Unit 18

132 Broadway, Unit 1

37 Westminster Ave, Unit 2

32-34 Fessenden Rd, Unit 2

104 Forest St, Unit 104

72-74 Harlow St, Unit 72

116 Medford St, Unit 1

32 Fessenden Rd, Unit #2

9 Bartlett Ave, Unit 2

28 Wadsworth Rd

80 Allen St

80 Allen St

32 River St

47 Webster St, Unit 47

308 Washington St

32 River St

27 Michael St

22 Cleveland St, Unit A

2012 Symmes Cir, Unit 1

20 Grove Street Pl

122 Oakland Ave

22 Patrick St

52 Webster St, Unit 52

32 Washington 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 | $3,009 | $2,275 | $4,000 |
Winchester 3 Bedroom Homes for Rent | $3,938 | $2,500 | $6,500 |
Winchester 4 Bedroom Homes for Rent | $4,946 | $3,200 | $7,500 |
Winchester 5 Bedroom Homes for Rent | $6,202 | $2,800 | $10,000+ |
Winchester 6 Bedroom Homes for Rent | $8,019 | $4,600 | $10,000+ |
Winchester 7 Bedroom Homes for Rent | $7,837 | $7,700 | $7,975 |
Browse Top Homes for Rent in Winchester
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Frequently Asked Questions about Winchester
What type of rentals are currently available in Winchester?
There are currently 986 Apartments for Rent in Winchester, MA with pricing that ranges from $1,500 to $12,069. There are also 553 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,795 to $25,000.
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 $1,795 to $25,000 with an average monthly rent of $4,813.
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 $2,600 to $12,069, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,500 to $6,500. Four Bedroom Single-Family rentals are also available starting from $3,200 and Four Bedroom Apartments start at $3,249.
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.

Apartment Animals: What Renters Should Know About Pet Policies & Service Animals
Written by: Andrea Lee Negroni, JD
If you’re considering an apartment that accepts pets, it’s wise to learn about the rules that apply to animals in apartments. Conversely, if you want a no-pets building, you should understand what “no pets” means.

Battling the Butts: Your Guide to the Reality of Smoke-Free Renting
Written by: Andrea Lee Negroni, JD
While many apartment buildings are “no smoking” properties, it’s hard to know exactly how many. In 2017, the National Apartment Association reported more than half of rental properties had smoke free policies.

Understanding Amenity Fees: Know Where You Might Be Able to Save Money
Written by: Amber Kanuckel
With the rising costs of housing, a lot of renters are asking this question: Is it possible to opt out of various amenities that your rental property offers so that you can avoid paying the fees.