222 S Kent St
WinchesterVA22601
Cheap Homes for Rent in Downtown Winchester Neighborhood of Winchester, VA from $1,100 (13 Rentals)
Search the lowest-cost Homes available for rent right now in the Downtown Winchester area of Winchester.
448 N Loudoun St
WinchesterVA22601
307 S Kent St
WinchesterVA22601
550 N Loudoun St, Unit 4
550 N Loudoun St
WinchesterVA22601
233 Kern St
WinchesterVA22601
412 Diehl St
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.
224 East St
WinchesterVA22601
382 Woodstock Ln
WinchesterVA22601
109 E Pall Mall St
WinchesterVA22601
2256 Roosevelt Blvd
WinchesterVA22601
615 S Braddock St
WinchesterVA22601
311 S Kent 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.
21 S Stewart St
WinchesterVA22601
Showing Results 1-13, Page 1 of 1
Downtown Winchester, Winchester, VA Local Guide
How much does it cost to rent a home in Downtown Winchester?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Downtown Winchester 2 Bedroom Homes for Rent | $1,621 | $1,295 | $2,200 |
| Downtown Winchester 3 Bedroom Homes for Rent | $2,154 | $1,550 | $3,700 |
| Downtown Winchester 4 Bedroom Homes for Rent | $2,600 | $2,600 | $2,600 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Homes for Rent in this Neighborhood
There are currently 13 rentals with your search options within a 2 mile radius of the Downtown Winchester Neighborhood of Winchester, VA.
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Downtown Winchester, Winchester, VA Local Guide
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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 $1,600. 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 Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| PEMBERTON | 2 BEDROOM 2 BATH | 2BR,2BA | $1,600 |
| Blue Ridge Apartments | 2 Bedroom 1 Bath - Reno | 2BR,1BA | $1,620 |
| The Local | The Graduate | 1BR,1BA | $1,700 |
| Fort Collier Terrace | 3 Beds 1.5 Baths | 3BR,1BA | $1,752 |
| CEDAR HILL APARTMENTS | 2 BEDROOM 2 BATH with DEN | 3BR,2BA | $1,800 |
Best Value Apartments for Rent in Downtown Winchester, VA
As of June 11, 2026 the best value apartment in the Downtown Winchester area is the $1.65 price per square foot Hollingsworth Model at The Lofts at Jubal Square in the in the Park Place neighborhood starting from $2,393. The second greatest value Downtown Winchester apartment is the 2 BEDROOM 2 BATH with DEN Model at CEDAR HILL APARTMENTS starting at $1,800 with a $1.52 price per square foot in the Kernstown neighborhood. Here is today’s list of the best values for Downtown Winchester apartments based on price per square foot:
| Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| The Lofts at Jubal Square | Hollingsworth | 3BR,2BA | $1.65 |
| CEDAR HILL APARTMENTS | 2 BEDROOM 2 BATH with DEN | 3BR,2BA | $1.52 |
| Fort Collier Terrace | 3 Beds 1.5 Baths | 3BR,1.5BA | $1.75 |
| Denstock Meadow Branch LLC | Gala | 1BR,1BA | $2.09 |
| PEMBERTON | 2 BEDROOM 1 BATH | 2BR,1BA | $1.74 |
| 208 N Kent St, Unit 208 N. Kent St - Unit A | 208 N Kent St | 2BR,1BA | $1.82 |
| 210 N Kent St, Unit A | 210 N Kent St | 2BR,1BA | $1.85 |
| Blue Ridge Apartments | 2 Bedroom 1 Bath - Reno | 2BR,1BA | $1.96 |
| The Local | The Graduate | 1BR,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.
Read Article
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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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 LifestyleDowntown Winchester, Winchester, VA
Ranked #3
Among cities in Virginia for Apartment listings with Pet Friendly Amenities.
Pet Friendliness Lifestyle Score
3.5Pet Friendly
Frequently Asked Questions about Downtown Winchester
What type of rentals are currently available in Downtown Winchester?
There are currently 97 Apartments for Rent in Downtown Winchester, VA with pricing that ranges from $900 to $3,900. There are also 46 Single Family Homes for rent, Condos, and Townhome rentals currently available in Downtown Winchester ranging from $1,100 to $3,700.
What is the current price range for Rental Homes in Downtown Winchester?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Downtown Winchester ranges from $1,100 to $3,700 with an average monthly rent of $1,963.
How much are larger Three and Four Bedroom Rentals in Downtown Winchester?
For those who are looking for larger living arrangements, Three Bedroom Apartments in Downtown Winchester range from $1,400 to $3,348, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,550 to $3,700. Four Bedroom Single-Family rentals are also available starting from $2,600 and Four Bedroom Apartments start at $3,900.
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
How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Written by: Robin Stewart
Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.
Pet-Friendly Renting: Everything You Need to Know Before You Move
Written by: Christine Leonard, Esq.
For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.
Creative Ways Developers Reimagine Retail Spaces as Residential Units
Written by: Robin Stewart
Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.
Neighborhood and Market Insights: How to Choose the Right Area to Rent
Written by: Robin Stewart
Apartment-hunting can be a gargantuan task. Renters have a wish list of items—some luxuries, some necessities—but finding what you seek in the right place is perhaps the most important part of the journey.