270 Cross St
WinchesterMA01890
Pet Friendly Homes for Rent in Winchester, MA (68 Rentals)
Homes for rent in Winchester that love your dogs or cats as much as you do!
171 Swanton St
WinchesterMA01890
200 Swanton St
WinchesterMA01890
7 Ridge St
WinchesterMA01890
79 Bacon St
WinchesterMA01890
270 Cross St
WinchesterMA01890
31 Fells Rd
WinchesterMA01890
555 Main St
WoburnMA01801
40 Campbell St
WoburnMA01801
3 Day Cir
WoburnMA01801
Moving to Boston Without Losing Your Mind: A Renter’s Guide to a Smooth Move
Moving to Boston? Discover how to handle unique rental rules, avoid common moving day pitfalls, and prepare for your first winter in the city
353 Washington St
ArlingtonMA02474
333 Massachusetts Ave
ArlingtonMA02474
72 Harlow St, Unit 72
72 Harlow St
ArlingtonMA02474
14 Kings Ct
ArlingtonMA02474
61 Wollaston Ave, Unit 61 Wollaston Ave - 2
61 Wollaston Ave
ArlingtonMA02476
15 Campbell Rd
ArlingtonMA02476
25 Falmouth Rd
ArlingtonMA02474
258 Boston Ave
MedfordMA02155
21 Jerome St
MedfordMA02155
10 Greenleaf Ave, Unit 1
10 Greenleaf Ave
MedfordMA02155
Renters Insurance 101: What It Is, What It Covers, and Why You Need It
From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.
120 Jerome St, Unit 1
120 Jerome St
MedfordMA02155
120 Jerome St
MedfordMA02155
177 Central St
StonehamMA02180
42 Belknap St
SomervilleMA02144
56 Gordon St, Unit 1
56 Gordon St
SomervilleMA02144
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$8,749
Total Monthly Price
Pet FriendlyDogs and Cats AllowedTotal Monthly Price
Base Rent
$8,318
Required Monthly Fees
$431
Total Monthly Price
$8,749
Pet Details
3 Chapel Way, Unit SI ID1387521P
3 Chapel WayStoneham, MA 02180
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$2,000Pet FriendlyCats and Dogs Allowed
Pet Details
167-169 Summer St #B, Unit #B
167-169 Summer StArlington, MA 02474
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$5,500Pet FriendlyDogs and Cats Allowed
Pet Details
167-169 Summer St #1, Unit #1
167-169 Summer StArlington, MA 02474
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$4,300Pet FriendlyDogs and Cats Allowed
Pet Details
163 Main St, Unit 1
163 Main StMedford, MA 02155
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$3,000Pet FriendlyDogs and Cats Allowed
Pet Details
80 Hillsdale Rd, Unit 2
80 Hillsdale RdMedford, MA 02155
What It Really Costs to Live in Boston: A Local Renter’s Guide
Thinking of moving to Boston? Discover the real cost of living in the city. Our local expert guide breaks down rent, hidden utility costs, transportation tips, and neighborhood tradeoffs to help you budget smarter.
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$2,950Pet FriendlyCats and Dogs Allowed
Pet Details
35 Summit St, Unit 35
35 Summit StArlington, MA 02474
21 Jerome St
MedfordMA02155
19-21-21 Mt Vernon St, Unit B
19-21-21 Mt Vernon St
ArlingtonMA02476
97 W Quincy St
SomervilleMA02144
49 Broadway, Unit 9
49 Broadway
ArlingtonMA02474
82 Arlmont St
ArlingtonMA02476
54 Clark St
MedfordMA02155
15 Governors Ave, Unit 28
15 Governors Ave
MedfordMA02155
15 Governors Ave, Unit 2
15 Governors Ave
MedfordMA02155
15 Governors Ave, Unit 24
15 Governors Ave
MedfordMA02155
Close to Boston, Easier to Rent: Your Guide to 5 Key Neighboring Cities
Find your perfect apartment outside Boston. We review Quincy, Braintree, Malden, Somerville, and Lynn, covering local hotspots, commute options, and available rental types.
15 Governors Ave, Unit 22
15 Governors Ave
MedfordMA02155
15 Governors Ave, Unit 28
15 Governors Ave
MedfordMA02155
15 Governors Ave, Unit 2
15 Governors Ave
MedfordMA02155
15 Governors Ave, Unit 24
15 Governors Ave
MedfordMA02155
47 Curtis Ave, Unit 3
47 Curtis Ave
SomervilleMA02144
47 Curtis Ave, Unit 1
47 Curtis Ave
SomervilleMA02144
74 Beach St
WoburnMA01801
27 Highland St
WoburnMA01801
555 Main St
WoburnMA01801
61 Dudley St
ArlingtonMA02476
How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.
Showing Results 1-50, Page 1 of 2
Winchester, MA Local Guide
How much does it cost to rent a home in Winchester?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winchester 2 Bedroom Homes for Rent | $3,101 | $2,300 | $4,750 |
| Winchester 3 Bedroom Homes for Rent | $4,129 | $2,900 | $6,500 |
| Winchester 4 Bedroom Homes for Rent | $5,290 | $2,850 | $9,750 |
| Winchester 5 Bedroom Homes for Rent | $8,751 | $4,900 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $8,941 | $6,495 | $10,000+ |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Top Homes for Rent in Winchester
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Winchester, MA Local Guide
- Winchester Neighborhoods
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10 Hidden Costs of Renting You Should Budget for Before Signing a Lease
Avoid financial stress when renting. Learn about the 10 most common hidden costs—from pet fees to utilities—you must budget for before you sign a lease.
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Boston Neighborhood Guide: Living Near UMass, MGH, and State Street
Get the local scoop! ApartmentHomeLiving's Boston Expert reveals the best neighborhoods to rent for employees of UMass Boston, Mass General Hospital, State Street, and more.
Read ArticleTop Neighborhoods Near Boston Colleges and Universities
Learn About the Best Neighborhoods to Rent Near College Campuses in Boston, MA | Find Boston Off-Campus Student Housing at ApartmentHomeLiving.com
Read ArticleReal Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University
From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.
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Quick Rent Budget Calculator
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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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Remember the 3 Rules of Real Estate:Location, Location, Location!
Explore Winchester, MA Rentals by Map
See the most popular apartments and homes in Winchester, MA
Frequently Asked Questions about Winchester
What type of rentals are currently available in Winchester?
There are currently 407 Apartments for Rent in Winchester, MA with pricing that ranges from $1,000 to $20,951. There are also 278 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $985 to $20,000.
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 $985 to $20,000 with an average monthly rent of $4,687.
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 $6,000, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,900 to $6,500. Four Bedroom Single-Family rentals are also available starting from $2,850 and Four Bedroom Apartments start at $3,300.
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.
Helpful Local Expert Guides
Moving to Boston Without Losing Your Mind: A Renter’s Guide to a Smooth Move
Written by: Amelia Ramstead
Hello! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston.
What It Really Costs to Live in Boston: A Local Renter's Guide
Written by: Amelia Ramstead
Hello! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston.
Close to Boston, Easier to Rent: Your Guide to 5 Key Neighboring Cities
Written by: Amelia Ramstead
Hello! I’m Amelia, your ApartmentHomeLiving.com expert for Boston!
Top Short-Term Rental Neighborhoods in Boston: Tips from a Local Expert
Written by: Amelia Ramstead
Hi! I’m Amelia, your ApartmentHomeLiving.com expert for Boston, and I’m excited to help you find your next home!
Articles, How-To's, and Tips
Pet-Friendly Renting: Everything You Need to Know Before You Move
Written by: Christine Leonard, Esq.
For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.
First Apartment Regrets: Real Renters Share What They'd Do Differently
Written by: Robin Stewart
Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.
Renters Insurance 101: What It Is, What It Covers, and Why You Need It
Written by: Robin Stewart
Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.
Apartment Occupancy Rates: Renter Attraction vs Renter Retention
Written by: Robin Stewart
There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.