Cheap Apartments for Rent in the Historic District Winchester, VA from $1,000 (17 Rentals)

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

property at 208 W Boscawen 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 Now

208 W Boscawen St

WinchesterVA22601
property at 113 W Boscawen St

$1,350

Total Monthly Price

Total Monthly Price

Base Rent
$1,350

Total Monthly Price
$1,350

2 Bedroom, 1 Bath Home for Rent

Available Now

113 W Boscawen 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

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 432 Chase St

$1,095

Total Monthly Price

Total Monthly Price

Base Rent
$1,095

Total Monthly Price
$1,095

2 Bedroom, 1 Bath Condo for Rent

Available Mar 13

432 Chase St

WinchesterVA22601
property at 18 E Clifford St

$1,150

Total Monthly Price

Total Monthly Price

Base Rent
$1,150

Total Monthly Price
$1,150

2 Bedroom, 1 Bath Townhome for Rent

Available Mar 20

18 E Clifford St

WinchesterVA22601
property at 304 S Kent St

$1,195

Total Monthly Price

Total Monthly Price

Base Rent
$1,195

Total Monthly Price
$1,195

2 Bedroom, 1 Bath Townhome for Rent

Available Now

304 S Kent St

WinchesterVA22601
property at 24 W Cecil St

$1,200

Total Monthly Price

Total Monthly Price

Base Rent
$1,200

Total Monthly Price
$1,200

2 Bedroom, 1 Bath Condo for Rent

Available Now

24 W Cecil St

WinchesterVA22601
property at 123 E Leicester 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 Apr 1

123 E Leicester 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 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 235 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

235 Kern St

WinchesterVA22601
property at 103 W Germain St

$1,395

Total Monthly Price

Total Monthly Price

Base Rent
$1,395

Total Monthly Price
$1,395

2 Bedroom, 1 Bath Home for Rent

Available Now

103 W Germain St

WinchesterVA22601
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Raleigh Court
2 Bedroom Apartments

Raleigh Court

1 Raleigh CtWinchester, VA 22601
  • Utilities Included
property at 434 Fairmont Ave

$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

434 Fairmont 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 44 S Loudoun St

$1,400

Total Monthly Price

Total Monthly Price

Base Rent
$1,400

Total Monthly Price
$1,400

1 Bedroom, 1 Bath Condo for Rent

Available Now

44 S Loudoun St, Unit 9

44 S Loudoun St
WinchesterVA22601
property at 2 E Germain 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

2 E Germain St

WinchesterVA22601

Historic District, Winchester, VA Local Guide

Cheapest Available Historic District Apartments for Rent

 
Apartment ListingModel NameBed/BathPriced From
210 S Cameron St2 Bedroom2BR,2BA$2,100

Best Value Apartments for Rent in Historic District, VA

As of March 12, 2026 the best value apartment in the Historic District area is the $1.50 price per square foot 25 W Boscawen St Model at 25 W Boscawen St, Unit 3 in the in the Park Place neighborhood starting from $1,350. The second greatest value Historic District apartment is the 342 Fairmont Ave Model at 342 Fairmont Ave, Unit Apt 3 starting at $1,975 with a $2.32 price per square foot in the Park Place neighborhood. Here is today’s list of the best values for Historic District apartments based on price per square foot:

Apartment ListingModel NameBed/BathPrice Per Sq.Ft.
25 W Boscawen St, Unit 325 W Boscawen St1BR,1.5BA$1.50
342 Fairmont Ave, Unit Apt 3342 Fairmont Ave2BR,1BA$2.32
210 N Kent St, Unit A210 N Kent St2BR,1BA$1.85
210 S Cameron St1 Bedroom1BR,1BA$2.40
114 N Loudoun StStudioStudio ,1BA$4.57

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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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.

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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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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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Frequently Asked Questions about Cheap Historic District Apartments

How much is rent for a Cheap One Bedroom Historic District Apartment?

The lowest price for a Cheap One Bedroom Historic District Apartment is $1,800 at 114 N Loudoun St.

What is the lowest price for a Cheap Two Bedroom Historic District Apartment for rent?

Today's best deal for a Cheap Two Bedroom Apartment in Historic District is starting from $2,100 at 210 S Cameron St.

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

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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.

decorative image for Renting with Roommates: Realistic Expectations for Shared Lease article

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.