Cheap Apartments for Rent in the Downtown Winchester Neighborhood of Winchester, VA from $800 (15 Rentals)

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

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 208 W Boscawen St

$1,300 - $1,450

1 To 2 Bedroom Rentals

Available Now

208 W Boscawen St

WinchesterVA22601
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Pine Plaza
2 to 3 Bedroom Apartments

Pine Plaza

2237 Taft CirWinchester, VA 22601

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 318 S Braddock St

$1,000

1 Bedroom, 1 Bath Home for Rent

Available Now

318 S Braddock St

WinchesterVA22601
property at 24 W Cecil St

$1,200

2 Bedroom, 1 Bath Condo for Rent

Available Now

24 W Cecil St

WinchesterVA22601

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Downtown Winchester, Winchester, VA Local Guide

Cheapest Available Downtown Winchester Apartments for Rent

 

The cheapest available apartment rental in the Downtown Winchester area of Winchester, VA is a 1 Bed unit found at ZeroPak Apartments priced from $1,013. North Winchester Apartments has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,150. Here are the most affordable Downtown Winchester apartments for rent in Winchester, VA:

Apartment ListingModel NameBed/BathPriced From
ZeroPak Apartments1 Bedroom1BR,1BA$1,013
North Winchester ApartmentsOne Bedroom1BR,1BA$1,150
Blue Ridge Apartments2 Bedroom 1 Bath Woodstock - Reno2BR,1BA$1,450
PEMBERTON2 BEDROOM 2 BATH2BR,2BA$1,580
HARRISON PLAZA RESIDENTIAL1 BEDROOM 1 BATH1BR,1BA$1,605

Best Value Apartments for Rent in Downtown Winchester, VA

As of February 07, 2026 the best value apartment in the Downtown Winchester area is the $1.74 price per square foot Hollingsworth Model at The Lofts at Jubal Square in the in the Downtown Winchester neighborhood starting from $2,517. The second greatest value Downtown Winchester apartment is the 1 Bedroom Model at ZeroPak Apartments starting at $1,013 with a $0.82 price per square foot in the Downtown Winchester neighborhood. Here is today’s list of the best values for Downtown Winchester apartments based on price per square foot:

Apartment ListingModel NameBed/BathPrice Per Sq.Ft.
The Lofts at Jubal SquareHollingsworth3BR,2BA$1.74
ZeroPak Apartments1 Bedroom1BR,1BA$0.82
Fort Collier Terrace3 Beds 1.5 Baths3BR,1.5BA$1.80
342 Fairmont Ave, Unit Apt 3342 Fairmont Ave2BR,1BA$2.32
North Winchester ApartmentsOne Bedroom1BR,1BA$1.51
The LocalThe Graduate1BR,1BA$2.79
301 S Braddock St, Unit 3301 S Braddock St1BR,1BA$2.80

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.

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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.

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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.

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Quick Rent Budget Calculator

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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
Downtown Winchester, Winchester, VA

Ranked #4

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

Pet Friendliness Lifestyle Score

3.0
Pet Friendly

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Frequently Asked Questions about Cheap Downtown Winchester Apartments

What is the price of a cheap apartment in Downtown Winchester?

The cheapest apartment in Downtown Winchester is ZeroPak Apartments which is listed at $1,013, while the average apartment in Downtown Winchester costs $3,900.

What types of apartments are the cheapest in Downtown Winchester?

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 3 regular apartments in Downtown Winchester that we think qualify as ‘cheap apartments’ that do not have special requirements to apply to rent.

How do the prices of cheap apartments compare to the average apartment in Downtown Winchester?

Cheap apartments in Downtown Winchester have an average cost of $328 which is $3,572 cheaper than the average rent for all rentals in Downtown Winchester.

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 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.

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18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property

Written by: Lauren Harrington

Renting your next home can feel thrilling and overwhelming at the same time.

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A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment

Written by: Bob Mallory

Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.

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Renting with Roommates: Realistic Expectations for Shared Lease

Written by: Christine Leonard, Esq.

Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.