1816 Valley Ave
WinchesterVA22601
Cheap Apartments for Rent in the Old Town Neighborhood of Winchester, VA from $900 (23 Rentals)
Search the lowest-cost Apartments available for rent right now in the Old Town area of Winchester.
close
View Me
$9951 Bedroom Apartments Available Jul 1
406 N Loudoun St, Unit 3
406 N Loudoun StWinchester, VA 22601
close
View Me
$1,013 - $1,685
Plus Fees12 Month Lease Term
1 to 3 Bedroom Apartments Contact Us For AvailabilityZeroPak Apartments
570 N Cameron StWinchester, VA 22601
515 N Loudoun St
WinchesterVA22601
142 N Washington St
WinchesterVA22601
close
View Me
$1,3001 Bedroom Apartments Available Aug 1
115 W Monmouth St, Unit 2
115 W Monmouth StWinchester, VA 22601
506 N Loudoun St
WinchesterVA22601
What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Learn the official definition (spending 30% or more of your gross income on housing) and how to calculate your exact rent-to-income ratio. This guide offers expert tips on factoring in total housing costs (including utilities and fees) and budgeting accurately to avoid unnecessary financial strain.
523 S Cameron St
WinchesterVA22601
4 W Cork St
WinchesterVA22601
382 Woodstock Ln
WinchesterVA22601
7 W Piccadilly St
WinchesterVA22601
105 N Loudoun St
WinchesterVA22601
222 S Kent St
WinchesterVA22601
307 S Kent St
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.
233 Kern St
WinchesterVA22601
412 Diehl St
WinchesterVA22601
224 East St
WinchesterVA22601
close
View Me
2 Bedroom Apartments
Raleigh Court
1 Raleigh CtWinchester, VA 22601
109 E Pall Mall St
WinchesterVA22601
204 E Whitlock Ave
WinchesterVA22601
311 S Kent St
WinchesterVA22601
Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.
615 S Braddock St
WinchesterVA22601
21 S Stewart St
WinchesterVA22601
Showing Results 1-23, Page 1 of 1
Old Town, Winchester, VA Local Guide
How much does it cost to rent an apartment in Old Town?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Old Town Studio Apartments | $1,712 | $1,700 | $1,725 |
| Old Town 1 Bedroom Apartments | $1,689 | $995 | $2,200 |
| Old Town 2 Bedroom Apartments | $1,936 | $1,218 | $2,600 |
| Old Town 3 Bedroom Apartments | $1,821 | $1,400 | $2,100 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Apartments in this Neighborhood
There are currently 23 rentals with your search options within a 1 mile radius of the Old Town Neighborhood of Winchester, VA.
See all Apartments in WinchesterExplore Winchester
Old Town, Winchester, VA Local Guide
- Nearby Winchester neighborhoods
- Nearby Cities
- ZIP codes
- Local Counties
- School Districts
Best Value Apartments for Rent in Old Town, VA
As of June 20, 2026 the best value apartment in the Old Town area is the $1.44 price per square foot 21 N Braddock St Model at 21 N Braddock St in the in the Park Place neighborhood starting from $1,800. The second greatest value Old Town apartment is the 208 N Kent St Model at 208 N Kent St, Unit 208 N. Kent St - Unit A starting at $1,550 with a $1.82 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 | $1.44 |
| 208 N Kent St, Unit 208 N. Kent St - Unit A | 208 N Kent St | 2BR,1BA | $1.82 |
| 210 N Kent St, Unit A | 210 N Kent St | 2BR,1BA | $1.85 |
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.
Read ArticleQuick 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 Old Town area?
If you’re an expert on all things Old Town, tell us what you love (and don't) by rating it and writing a review.
Write a Review
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
School data provided by Great Schools
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
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.
How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Written by: Robin Stewart
Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.
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.
Creative Ways Developers Reimagine Retail Spaces as Residential Units
Written by: Robin Stewart
Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.