Cheap Apartments for Rent in the Downtown Winchester Neighborhood of Winchester, VA from $800 (26 Rentals)

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

property at 1816 Valley Ave

$995

Total Monthly Price

Total Monthly Price

Base Rent
$995

Total Monthly Price
$995

1 Bedroom, 1 Bath Home for Rent

Available Now

1816 Valley Ave

WinchesterVA22601
property at 107 Morgan St

$1,200

Total Monthly Price

Total Monthly Price

Base Rent
$1,200

Total Monthly Price
$1,200

Studio, 1 Bath Home for Rent

Available May 28

107 Morgan St

WinchesterVA22601
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
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Fort Collier Terrace
Rent Specials
$1,272 - $1,847
Total Monthly Price

Total Monthly Price

Base Rent
$1,245 - $1,820
Required Monthly Fees
$27

Total Monthly Price
$1,272 - $1,847
1 to 3 Bedroom Apartments Available Now

Fort Collier Terrace

900-1024 N Braddock StWinchester, VA 22601
Corporate Housing
  • Verified
  • Customer Reviewed
  • 3D Tour

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 142 N Washington 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

142 N Washington St

WinchesterVA22601
property at 402 S Loudoun St

$1,300 - $1,550

Total Monthly Price

Total Monthly Price

Base Rent
$1,300

Total Monthly Price
$1,300

Studio Rentals

Available Now

402 S Loudoun St

WinchesterVA22601
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Blue Ridge Apartments
Rent Specials
$1,420 - $1,745
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,375 - $1,700
Required Monthly Fees
Varies

Total Monthly Price
Varies
2 to 4 Bedroom Apartments Available Now

Blue Ridge Apartments

2260 Wilson BlvdWinchester, VA 22601
Pet Friendly
  • Verified
  • Customer Reviewed
  • 3D Tour
property at 312 Amherst St

$1,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,500

Total Monthly Price
$1,500

3 Bedroom, 1.5 Bath Townhome for Rent

Available Jun 1

312 Amherst St

WinchesterVA22601
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Pine Plaza
2 to 3 Bedroom Apartments

Pine Plaza

2237 Taft CirWinchester, VA 22601

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 222 S Kent St

$1,100

Total Monthly Price

Total Monthly Price

Base Rent
$1,100

Total Monthly Price
$1,100

1 Bedroom, 1 Bath Home for Rent

Available Now

222 S Kent St

WinchesterVA22601
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 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 550 N Loudoun St

$1,350

Total Monthly Price

Total Monthly Price

Base Rent
$1,350

Total Monthly Price
$1,350

1 Bedroom, 1 Bath Condo for Rent

Available Now

550 N Loudoun St, Unit 4

550 N Loudoun St
WinchesterVA22601

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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 Jun 1

224 East 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 2256 Roosevelt Blvd

$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

2256 Roosevelt Blvd

WinchesterVA22601
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

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 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 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

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 2 Beds unit found at PEMBERTON priced from $1,575. Blue Ridge Apartments has the second lowest priced unit, which is a 2 Beds apartment currently listed from $1,620. Here are the most affordable Downtown Winchester apartments for rent in Winchester, VA:

Apartment ListingModel NameBed/BathPriced From
PEMBERTON2 BEDROOM 1 BATH2BR,1BA$1,575
Blue Ridge Apartments2 Bedroom 1 Bath - Reno2BR,1BA$1,620
The LocalThe Graduate1BR,1BA$1,700
Fort Collier Terrace3 Beds 1.5 Baths3BR,1BA$1,822
The Lofts at Jubal SquareMorgan1BR,1BA$1,843
Denstock Meadow Branch LLCFuji1BR,1BA$1,868

Best Value Apartments for Rent in Downtown Winchester, VA

As of May 28, 2026 the best value apartment in the Downtown Winchester area is the $1.82 price per square foot 3 Beds 1.5 Baths Model at Fort Collier Terrace in the in the Steeplechase neighborhood starting from $1,822. The second greatest value Downtown Winchester apartment is the Morgan Model at The Lofts at Jubal Square starting at $1,843 with a $1.91 price per square foot in the Park Place 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.
Fort Collier Terrace3 Beds 1.5 Baths3BR,1.5BA$1.82
The Lofts at Jubal SquareMorgan1BR,1BA$1.91
PEMBERTON2 BEDROOM 1 BATH2BR,1BA$1.75
Denstock Meadow Branch LLCFuji1BR,1BA$2.13
Blue Ridge Apartments2 Bedroom 1 Bath - Reno2BR,1BA$1.96
The LocalThe Graduate1BR,1BA$2.79

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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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.

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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 #3

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 The Local which is listed at $1,700, 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 12 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 $1,369 which is $2,531 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.

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