413 E Cork St
WinchesterVA22601
Cheap Homes for Rent in Old Town Neighborhood of Winchester, VA from $900 (11 Rentals)
Search the lowest-cost Homes available for rent right now in the Old Town area of Winchester.
382 Woodstock Ln
WinchesterVA22601
376 Woodstock Ln
WinchesterVA22601
313 Virginia Ave
WinchesterVA22601
127-A Peyton Street
WinchesterVA22601
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.
219 Millwood Ave
WinchesterVA22601
312 Shawnee Ave, Unit 0422
312 Shawnee Ave
WinchesterVA22601
211 Sharp St
WinchesterVA22601
44 S Loudoun St
WinchesterVA22601
235 Millwood Ave
WinchesterVA22601
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.
300-302 N Kent St
WinchesterVA22601
Showing Results 1-11, Page 1 of 1
Old Town, Winchester, VA Local Guide
How much does it cost to rent a home in Old Town?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Old Town 2 Bedroom Homes for Rent | $1,678 | $1,400 | $2,400 |
| Old Town 3 Bedroom Homes for Rent | $1,946 | $1,600 | $2,500 |
| Old Town 4 Bedroom Homes for Rent | $2,350 | $2,000 | $2,700 |
Browse Homes for Rent in this Neighborhood
There are currently 11 rentals with your search options within a 1 mile radius of the Old Town Neighborhood of Winchester, VA.
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Old Town, Winchester, VA Local Guide
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Best Value Apartments for Rent in Old Town, VA
As of November 02, 2025 the best value apartment in the Old Town area is the $1.58 price per square foot 446 N Loudoun St Model at 446 N Loudoun St, Unit 1 in the in the Park Place neighborhood starting from $1,895. The second greatest value Old Town apartment is the 111 E Monmouth St Model at 111 E Monmouth St, Unit Downstairs Unit starting at $1,275 with a $1.59 price per square foot in the Park Place neighborhood. Here is today’s list of the best values for Old Town apartments based on price per square foot:
| Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| 446 N Loudoun St, Unit 1 | 446 N Loudoun St | 3BR,1BA | $1.58 |
| 111 E Monmouth St, Unit Downstairs Unit | 111 E Monmouth St | 2BR,1BA | $1.59 |
| 342 Fairmont Ave, Apt 5, Unit #5 FULLY FURNISHED RENTAL Retro Loves Company | 342 Fairmont Ave, Apt 5 | 1BR,1BA | $2.62 |
Apartment Common Area Rules: What Renters Need to Know
From the lounge to the laundry room, understand your rights and responsibilities in shared apartment spaces. Get tips on pet rules, noise, and security.
Read Article
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.
Read ArticleThe 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 ArticleQuick Rent Budget Calculator
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Pet Friendly LifestyleOld Town, Winchester, VA
Ranked #6
Among cities in Virginia for Apartment listings with Pet Friendly Amenities.
Pet Friendliness Lifestyle Score
3.0Pet Friendly
Best Local Schools in Old Town, Winchester, VA
School data provided by Great Schools
Frequently Asked Questions about Old Town
What type of rentals are currently available in Old Town?
There are currently 61 Apartments for Rent in Old Town, VA with pricing that ranges from $995 to $2,600. There are also 29 Single Family Homes for rent, Condos, and Townhome rentals currently available in Old Town ranging from $900 to $2,700.
What is the current price range for Rental Homes in Old Town?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Old Town ranges from $900 to $2,700 with an average monthly rent of $1,659.
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.
Apartment Common Area Rules: What Renters Need to Know
Written by: Christine Leonard, Esq.
Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.
How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!
The Rental Move-In Inspection Checklist: A Guide for Renters
Written by: Trey Huguley
The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Written by: Christine Leonard, Esq.
For many people, obstacles can arise during the rental application process for a variety of issues.