377 National Ave
WinchesterVA22601
Cheap Homes for Rent in the Old Town Neighborhood of Winchester, VA from $750 (9 Rentals)
Search the lowest-cost Homes available for rent right now in the Old Town area of Winchester.
552 Fremont St
WinchesterVA22601
5 E Pall Mall St, Unit 7
5 E Pall Mall St
WinchesterVA22601
204 E Whitlock Ave
WinchesterVA22601
Rent According to Income: A Look at Income-Restricted Rentals
Find income-restricted rentals and housing subsidies. Explore government programs designed to help low-income families secure stable, affordable housing.
222 E Whitlock Ave
WinchesterVA22601
1001 S Cameron St
WinchesterVA22601
346 Gray Ave
WinchesterVA22601
305 S Kent St
WinchesterVA22601
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.
221 Baker St
WinchesterVA22601
Showing Results 1-9, 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 | $1,523 | $1,100 | $1,900 |
| Old Town 3 Bedroom Homes for Rent | $1,818 | $1,350 | $2,525 |
| Old Town 4 Bedroom Homes for Rent | $2,298 | $2,100 | $2,495 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Homes for Rent in this Neighborhood
There are currently 9 rentals with your search options within a 1 mile radius of the Old Town Neighborhood of Winchester, VA.
Explore Winchester
Old Town, Winchester, VA Local Guide
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Cheapest Available Old Town Apartments for Rent
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| 19-49 West Bond Street | 3BR/1.0BA | 3BR,1BA | $1,600 |
Best Value Apartments for Rent in Old Town, VA
As of August 27, 2026 the best value apartment in the Old Town area is the $1.36 price per square foot 21 N Braddock St Model at 21 N Braddock St in the in the Park Place neighborhood starting from $1,700. The second greatest value Old Town apartment is the 318 S Cameron St Model at 318 S Cameron St, Unit Apt A starting at $1,300 with a $1.44 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. |
|---|---|---|---|
| 21 N Braddock St | 21 N Braddock St | 2BR,1BA | $1.36 |
| 318 S Cameron St, Unit Apt A | 318 S Cameron St | 2BR,1BA | $1.44 |
| 342 Fairmont Ave, Unit Apt 3 | 342 Fairmont Ave | 2BR,1BA | $2.47 |
| 342 Fairmont Ave, Apt #8, Unit Comfortable In-Towner | 342 Fairmont Ave, Apt #8 | 1BR,1BA | $2.65 |
| 342 Fairmont Ave, Apt 5, Unit #5 FULLY FURNISHED RENTAL Retro Loves Company | 342 Fairmont Ave, Apt 5 | 1BR,1BA | $2.65 |
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 Article
Real 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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Pet Friendly LifestyleOld Town, Winchester, VA
Ranked #7
Among cities in Virginia for Apartment listings with Pet Friendly Amenities.
Pet Friendliness Lifestyle Score
2.5Pet Friendly
Best Local Schools in Old Town, Winchester, VA
Daniel Morgan Middle School
Winchester City Public Schools
Public School - Grades 6-8 (642)
4 out of 10
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 68 Apartments for Rent in Old Town, VA with pricing that ranges from $995 to $2,600. There are also 34 Single Family Homes for rent, Condos, and Townhome rentals currently available in Old Town ranging from $750 to $2,525.
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 $750 to $2,525 with an average monthly rent of $1,701.
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.
Articles, How-To's, and Tips
Rent According to Income: A Look at Income-Restricted Rentals
Written by: Robin Stewart
The idea of affordable housing can be subjective. Every individual is in a different place financially and vocationally. What one may easily afford could be a struggle for someone else.
Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags
Written by: Robin Stewart
Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.
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.