377 National Ave
WinchesterVA22601
Cheap Homes for Rent in the Downtown Winchester Neighborhood of Winchester, VA from $750 (12 Rentals)
Search the lowest-cost Homes available for rent right now in the Downtown Winchester area of Winchester.
204 E Whitlock Ave
WinchesterVA22601
714 S Cameron St
WinchesterVA22601
1001 S Cameron St
WinchesterVA22601
346 Gray Ave
WinchesterVA22601
305 S Kent St
WinchesterVA22601
Rent According to Income: A Look at Income-Restricted Rentals
Find income-restricted rentals and housing subsidies. Explore government programs designed to help low-income families secure stable, affordable housing.
131 S Purcell Ave
WinchesterVA22601
2256 Roosevelt Blvd
WinchesterVA22601
502 N Loudoun St
WinchesterVA22601
230 E Whitlock Ave
WinchesterVA22601
21 S Stewart St
WinchesterVA22601
619 S Cameron St
WinchesterVA22601
Renters Insurance 101: What It Is, What It Covers, and Why You Need It
From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.
Showing Results 1-12, 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 | $1,596 | $1,250 | $1,995 |
| Downtown Winchester 3 Bedroom Homes for Rent | $1,819 | $1,395 | $2,525 |
| Downtown Winchester 4 Bedroom Homes for Rent | $2,383 | $2,100 | $2,650 |
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 12 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 1 Bed unit found at 008 priced from $1,250. North Winchester Apartments has the second lowest priced unit, which is a 2 Beds apartment currently listed from $1,300. Here are the most affordable Downtown Winchester apartments for rent in Winchester, VA:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| 008 | 1BR/1.0BA | 1BR,1BA | $1,250 |
| North Winchester Apartments | Two Bedroom | 2BR,2BA | $1,300 |
| Autumn Wind Apartments | The Shenandoah | 2BR,2BA | $1,443 |
| Blue Ridge Apartments | 2 Bedroom 1 Bath Woodstock - Reno | 2BR,1BA | $1,495 |
| PEMBERTON | 2 BEDROOM 2 BATH | 2BR,2BA | $1,550 |
Best Value Apartments for Rent in Downtown Winchester, VA
As of September 11, 2026 the best value apartment in the Downtown Winchester area is the $1.33 price per square foot 308 W Boscawen St Model at 308 W Boscawen St, Unit 308 W Boscawen Street Apt 2 in the in the Park Place neighborhood starting from $2,000. The second greatest value Downtown Winchester apartment is the Hollingsworth Model at The Lofts at Jubal Square starting at $2,388 with a $1.65 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 Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| 308 W Boscawen St, Unit 308 W Boscawen Street Apt 2 | 308 W Boscawen St | 3BR,1.5BA | $1.33 |
| The Lofts at Jubal Square | Hollingsworth | 3BR,2BA | $1.65 |
| 21 N Braddock St, Unit #3 | 21 N Braddock St | 2BR,1BA | $1.36 |
| PEMBERTON | 2 BEDROOM 2 BATH | 2BR,2BA | $1.57 |
| Autumn Wind Apartments | The Shenandoah | 2BR,2BA | $1.46 |
| 318 S Cameron St, Unit Apt A | 318 S Cameron St | 2BR,1BA | $1.44 |
| Fort Collier Terrace | 2 Beds 1.5 Baths | 2BR,1.5BA | $1.86 |
| North Winchester Apartments | Two Bedroom | 2BR,2BA | $1.50 |
| Stuart Hill | The Frederick | 1BR,1BA | $1.98 |
| Blue Ridge Apartments | 2 Bedroom 1 Bath - Reno | 2BR,1BA | $1.96 |
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
Navigating the Rental Market: Tips for First-Time Renters
Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.
Read ArticleReal 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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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 99 Apartments for Rent in Downtown Winchester, VA with pricing that ranges from $1,095 to $3,900. There are also 41 Single Family Homes for rent, Condos, and Townhome rentals currently available in Downtown Winchester ranging from $750 to $2,650.
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 $750 to $2,650 with an average monthly rent of $1,753.
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 $1,625 to $3,341, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,395 to $2,525. Four Bedroom Single-Family rentals are also available starting from $2,100 and Four Bedroom Apartments start at $2,110.
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
Rent According to Income: A Look at Income-Restricted Rentals
Written by: Robin Stewart
The idea of affordable housing can be subjective. Every individual is in a different place financially and vocationally. What one may easily afford could be a struggle for someone else.
Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My!
Written by: Robin Stewart
Where do you see yourself? When you think of home, sweet home, are you in a 3/2 apartment? Dreaming of a tall townhome? Maybe an industrial loft heavy on cool vibes is on your visioning board.
Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags
Written by: Robin Stewart
Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.
First Apartment Regrets: Real Renters Share What They'd Do Differently
Written by: Robin Stewart
Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.