12 Olde Village Dr
WinchesterMA01890
Luxury Homes for Rent in Winchester, MA (523 Rentals)
The most luxurious Homes in Winchester with high-end amenities, features, and finishes.
7 Thornberry Rd
WinchesterMA01890
148 Forest St
WinchesterMA01890
32 Surrey Rd
WinchesterMA01890
270 Cross St
WinchesterMA01890
171 Swanton St
WinchesterMA01890
345 Washington St, Unit 1
345 Washington St
WinchesterMA01890
186 Ridge St
WinchesterMA01890
271 Washington St
WinchesterMA01890
270 Cross St
WinchesterMA01890
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
32 Surrey Rd
WinchesterMA01890
115 Washington St
WinchesterMA01890
64 Highland Ave
WinchesterMA01890
75 Woodfall Rd
BelmontMA02478
75 Woodfall Rd
BelmontMA02478
39 Hopkins Rd
ArlingtonMA02476
34 Chetwynd Rd, Unit BF
34 Chetwynd Rd
SomervilleMA02144
80 Curtis St, Unit 1
80 Curtis St
SomervilleMA02144
80 Curtis St
SomervilleMA02144
17 Tesla Ave
MedfordMA02155
16 Chetwynd Rd
SomervilleMA02144
16 Chetwynd Rd
SomervilleMA02144
80 Curtis St
SomervilleMA02144
16 Chetwynd Rd
SomervilleMA02144
16 Chetwynd Rd
SomervilleMA02144
232 Fulton St
MedfordMA02155
120 Jerome St
MedfordMA02155
232 Fulton St
MedfordMA02155
120 Jerome St, Unit T
120 Jerome St
MedfordMA02155
232 Fulton St
MedfordMA02155
120 Jerome St, Unit 120
120 Jerome St
MedfordMA02155
232 Fulton St, Unit 232
232 Fulton St
MedfordMA02155
232 Fulton St
MedfordMA02155
120 Jerome St
MedfordMA02155
120 Jerome St
MedfordMA02155
232 Fulton St
MedfordMA02155
232 Fulton St, Unit T
232 Fulton St
MedfordMA02155
232 Fulton St
MedfordMA02155
120 Jerome St
MedfordMA02155
232 Fulton St
MedfordMA02155
120 Jerome St
MedfordMA02155
232 Fulton St
MedfordMA02155
232 Fulton St
MedfordMA02155
120 Jerome St
MedfordMA02155
232 Fulton St
MedfordMA02155
120 Jerome St
MedfordMA02155
120 Jerome St, Unit #0
120 Jerome St
MedfordMA02155
120 Jerome St
MedfordMA02155
120 Jerome St
MedfordMA02155
232 Fulton St
MedfordMA02155
Winchester, MA Local Guide
Downtown Winchester, Massachusetts by Moonshine4711 is licensed under CC BY-SA 3.0
How much does it cost to rent a home in Winchester?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Winchester 2 Bedroom Homes for Rent | $2,999 | $2,375 | $4,000 |
| Winchester 3 Bedroom Homes for Rent | $3,928 | $2,800 | $7,200 |
| Winchester 4 Bedroom Homes for Rent | $4,910 | $3,100 | $7,500 |
| Winchester 5 Bedroom Homes for Rent | $6,234 | $2,800 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $7,975 | $4,600 | $10,000+ |
| Winchester 7 Bedroom Homes for Rent | $7,837 | $7,700 | $7,975 |
Browse Top Homes for Rent in Winchester
Explore Winchester
Winchester, MA Local Guide
- Winchester 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.
Let everyone know!
Do you know the Winchester area?
If you’re an expert on all things Winchester, tell us what you love (and don't) by rating it and writing a review.
Write a Review
Frequently Asked Questions about Winchester
What type of rentals are currently available in Winchester?
There are currently 998 Apartments for Rent in Winchester, MA with pricing that ranges from $1,100 to $10,400. There are also 561 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,725 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 $1,725 to $25,000 with an average monthly rent of $4,810.
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 $7,135, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,800 to $7,200. Four Bedroom Single-Family rentals are also available starting from $3,100 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.
Renting Smart: Lease Basics Every Renter Needs
Written by: Christine Leonard, Esq.
Often, in the excitement of finding a new place to live, there’s a rush to make it happen, and - too often - a new tenant signs a lease without reading it carefully.
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.