Cheap Apartments for Rent in the Old Town Neighborhood of Winchester, VA from $900 (26 Rentals)

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Search the lowest-cost Apartments available for rent right now in the Old Town area of Winchester.

property at 434 N Kent St

$1,200

Total Monthly Price

Total Monthly Price

Base Rent
$1,200

Total Monthly Price
$1,200

2 Bedroom Rentals

Available Now

434 N Kent St

WinchesterVA22601
property at 105 N Loudoun St

$1,300

Total Monthly Price

Total Monthly Price

Base Rent
$1,300

Total Monthly Price
$1,300

1 Bedroom, 1 Bath Home for Rent

Available May 7

105 N Loudoun St

WinchesterVA22601
property at 127-A Peyton Street

$1,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,500

Total Monthly Price
$1,500

2 Bedroom, 1.5 Bath Townhome for Rent

Available Now

127-A Peyton Street

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.

property at 307 S Kent St

$1,295

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,295

Total Monthly Price
$1,295

2 Bedroom, 1 Bath Townhome for Rent

Available Jun 1

307 S Kent St

WinchesterVA22601
property at 309 S Kent St

$1,295

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,295

Total Monthly Price
$1,295

2 Bedroom, 1 Bath Townhome for Rent

Available Now

309 S Kent St

WinchesterVA22601
property at 233 Kern St

$1,350

Total Monthly Price

Total Monthly Price

Base Rent
$1,350

Total Monthly Price
$1,350

2 Bedroom, 1 Bath Townhome for Rent

Available Now

233 Kern St

WinchesterVA22601
property at 224 East St

$1,395

Total Monthly Price

Total Monthly Price

Base Rent
$1,395

Total Monthly Price
$1,395

2 Bedroom, 1 Bath Townhome for Rent

Available Now

224 East 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.

property at 515 N Loudoun St

$1,395

Total Monthly Price

Total Monthly Price

Base Rent
$1,395

Total Monthly Price
$1,395

1 Bedroom, 1 Bath Home for Rent

Available Now

515 N Loudoun St

WinchesterVA22601
property at 2 E Germain St

$1,400

Total Monthly Price

Total Monthly Price

Base Rent
$1,400

Total Monthly Price
$1,400

2 Bedroom, 1 Bath Home for Rent

Available Now

2 E Germain St

WinchesterVA22601
property at 412 Diehl St

$1,400

Total Monthly Price

Total Monthly Price

Base Rent
$1,400

Total Monthly Price
$1,400

2 Bedroom, 1 Bath Home for Rent

Available Now

412 Diehl St

WinchesterVA22601
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Raleigh Court
2 Bedroom Apartments

Raleigh Court

1 Raleigh CtWinchester, VA 22601
  • Utilities Included
property at 112 E Pall Mall St

$1,450

Total Monthly Price

Total Monthly Price

Base Rent
$1,450

Total Monthly Price
$1,450

2 Bedroom, 1 Bath Townhome for Rent

Available Now

112 E Pall Mall St

WinchesterVA22601
property at 737 S Kent St

$1,450

Total Monthly Price

Total Monthly Price

Base Rent
$1,450

Total Monthly Price
$1,450

2 Bedroom, 1 Bath Townhome for Rent

Available Now

737 S Kent St

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.

property at 220 Kimberly Way

$1,450

Total Monthly Price

Total Monthly Price

Base Rent
$1,450

Total Monthly Price
$1,450

2 Bedroom, 2.5 Bath Home for Rent

Available Now

220 Kimberly Way

WinchesterVA22601
property at 21 S Stewart St

$1,500

Total Monthly Price

Total Monthly Price

Base Rent
$1,500

Total Monthly Price
$1,500

2 Bedroom, 1 Bath Home for Rent

Available Now

21 S Stewart St

WinchesterVA22601
property at 109 E Pall Mall St

$1,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,500

Total Monthly Price
$1,500

2 Bedroom, 1 Bath Home for Rent

Available Now

109 E Pall Mall St

WinchesterVA22601
property at 609 Smithfield Ave

$1,575

Total Monthly Price

Total Monthly Price

Base Rent
$1,575

Total Monthly Price
$1,575

2 Bedroom, 1 Bath Townhome for Rent

Available Now

609 Smithfield Ave

WinchesterVA22601
property at 28 E Pall Mall St

$1,595

Total Monthly Price

Total Monthly Price

Base Rent
$1,595

Total Monthly Price
$1,595

2 Bedroom, 2 Bath Home for Rent

Available Now

28 E Pall Mall St

WinchesterVA22601
property at 1817 Henry Ave

$1,600

Total Monthly Price

Total Monthly Price

Base Rent
$1,600

Total Monthly Price
$1,600

2 Bedroom, 1.5 Bath Townhome for Rent

Available Now

1817 Henry Ave

WinchesterVA22601

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.

property at 1831 Henry Ave

$1,600

Total Monthly Price

Total Monthly Price

Base Rent
$1,600

Total Monthly Price
$1,600

2 Bedroom, 1.5 Bath Townhome for Rent

Available Now

1831 Henry Ave

WinchesterVA22601
property at 228 Opequon Ave

$1,600

Total Monthly Price

Total Monthly Price

Base Rent
$1,600

Total Monthly Price
$1,600

2 Bedroom, 1 Bath Home for Rent

Available Now

228 Opequon Ave

WinchesterVA22601

Old Town, Winchester, VA Local Guide

Cheapest Available Old Town Apartments for Rent

 
Apartment ListingModel NameBed/BathPriced From
ZeroPak Apartments2 Bedroom2BR,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 ListingModel NameBed/BathPrice Per Sq.Ft.
ZeroPak Apartments2 Bedroom2BR,1.5BA$0.78
130 Montague Ave130 Montague Ave2BR,1BA$2.00
342 Fairmont Ave, Unit Apt 3342 Fairmont Ave2BR,1BA$2.32
342 Fairmont Ave, Apt #8, Unit Comfortable In-Towner342 Fairmont Ave, Apt #81BR,1BA$2.62
342 Fairmont Ave, Apt 5, Unit #5 FULLY FURNISHED RENTAL Retro Loves Company342 Fairmont Ave, Apt 51BR,1BA$2.65
719 S Braddock St, Unit Master Bedroom719 S Braddock St1BR,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 Article
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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.

Read Article
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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
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The 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 Article
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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.

Read Article
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Quick 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.

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Pet Friendly Lifestyle
Old Town, Winchester, VA

Ranked #7

Among cities in Virginia for Apartment listings with Pet Friendly Amenities.

Pet Friendliness Lifestyle Score

2.5
Pet Friendly

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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

decorative image for A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back article

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.

decorative image for Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts  article

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.

decorative image for What Does “Rent Burdened” Mean? How Much Rent Is Too Much article

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.

decorative image for Maximizing Your Refund: Essential Tax Tips for Renters article

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.