
Cheap Apartments for Rent in the Old Town Neighborhood of Winchester, VA from $900 (26 Rentals)
Search the lowest-cost Apartments available for rent right now in the Old Town area of Winchester.


ZeroPak Apartments

434 N Kent St

105 N Loudoun St

406 N Loudoun St, Unit 14

127-A Peyton Street
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.

148 N Loudoun St

114 N Loudoun St

307 S Kent St

309 S Kent St

233 Kern St

224 East St
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.

515 N Loudoun St

2 E Germain St

412 Diehl St

Raleigh Court

112 E Pall Mall St

737 S Kent St
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.

220 Kimberly Way

21 S Stewart St

109 E Pall Mall St

609 Smithfield Ave

28 E Pall Mall St

1817 Henry Ave
The Art of the Rental Viewing: What to look for during a property tour
Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.

1831 Henry Ave

228 Opequon Ave
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 | $1,700 | $1,700 | $1,700 |
| Old Town 1 Bedroom Apartments | $1,852 | $900 | $2,200 |
| Old Town 2 Bedroom Apartments | $1,958 | $1,200 | $2,600 |
| Old Town 3 Bedroom Apartments | $1,592 | $1,499 | $1,685 |
Browse Apartments in this Neighborhood
There are currently 26 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
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Cheapest Available Old Town Apartments for Rent
 | Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| ZeroPak Apartments | 2 Bedroom | 2BR,1BA | $1,249 |
Best Value Apartments for Rent in Old Town, VA
As of May 06, 2026 the best value apartment in the Old Town area is the $0.78 price per square foot 2 Bedroom Model at ZeroPak Apartments in the in the Historic District neighborhood starting from $1,249. The second greatest value Old Town apartment is the 130 Montague Ave Model at 130 Montague Ave starting at $2,000 with a $2.00 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. |
|---|---|---|---|
| ZeroPak Apartments | 2 Bedroom | 2BR,1.5BA | $0.78 |
| 130 Montague Ave | 130 Montague Ave | 2BR,1BA | $2.00 |
| 342 Fairmont Ave, Unit Apt 3 | 342 Fairmont Ave | 2BR,1BA | $2.32 |
| 342 Fairmont Ave, Apt #8, Unit Comfortable In-Towner | 342 Fairmont Ave, Apt #8 | 1BR,1BA | $2.62 |
| 342 Fairmont Ave, Apt 5, Unit #5 FULLY FURNISHED RENTAL Retro Loves Company | 342 Fairmont Ave, Apt 5 | 1BR,1BA | $2.65 |
| 719 S Braddock St, Unit Master Bedroom | 719 S Braddock St | 1BR,1BA | $3.00 |
A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back
Learn the property manager's true secrets to a zero-deduction move-out. Use this step-by-step guide on documentation, cleaning, and lease-reading to reclaim your security deposit.
Read Article10 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.
Read ArticleDon'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 ArticleCash 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.
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.
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
Frequently Asked Questions about Cheap Old Town Apartments
What types of apartments are the cheapest in Old Town?
Student, low-income, and by-the-bed apartments are typically the cheapest rentals in most cities, though they require qualifying criteria to rent. There are 1 regular apartments in Old Town that we think qualify as ‘cheap apartments’ that do not have special requirements to apply to rent.
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

A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back
Written by: Lauren Harrington
I’m going to talk with you as a seasoned property manager and friend. So, let’s start with your security deposit. I want you to think about this guide as insider information. You deserve your deposit back.

Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts
Written by: Lauren Harrington
This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.

What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Written by: Lauren Harrington
This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.

Maximizing Your Refund: Essential Tax Tips for Renters
Written by: Christine Leonard, Esq.
Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.