1816 Valley Ave
WinchesterVA22601
Cheap Apartments for Rent in the Downtown Winchester Neighborhood of Winchester, VA from $800 (11 Rentals)
Search the lowest-cost Apartments available for rent right now in the Downtown Winchester area of Winchester.
800 Thomas Ct
WinchesterVA22601
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$1,013 - $1,6851 to 3 Bedroom Apartments Available Dec 15
ZeroPak Apartments
570 N Cameron StWinchester, VA 22601
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$1,050 - $1,3001 to 2 Bedroom Apartments Available Now
North Winchester Apartments
800 Thomas CtWinchester, VA 22601
545 N Loudoun 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.
24 Jackson Ave
WinchesterVA22601
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$1,2752 Bedroom Apartment Available Now
111 E Monmouth St, Unit Downstairs Unit
111 E Monmouth StWinchester, VA 22601
4 W Cork St
WinchesterVA22601
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413 E Cork 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.
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Downtown Winchester, Winchester, VA Local Guide
How much does it cost to rent an apartment in Downtown Winchester?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Downtown Winchester Studio Apartments | $1,500 | $1,300 | $1,700 |
| Downtown Winchester 1 Bedroom Apartments | $1,785 | $995 | $2,200 |
| Downtown Winchester 2 Bedroom Apartments | $1,743 | $1,249 | $3,100 |
| Downtown Winchester 3 Bedroom Apartments | $1,993 | $1,400 | $3,280 |
| Downtown Winchester 4 Bedroom Apartments | $2,087 | $1,775 | $2,400 |
Browse Apartments in this Neighborhood
There are currently 11 rentals with your search options within a 2 mile radius of the Downtown Winchester Neighborhood of Winchester, VA.
See all Apartments in WinchesterExplore Winchester
Downtown Winchester, Winchester, VA Local Guide
- Nearby Winchester neighborhoods
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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 North Winchester Apartments priced from $1,050. Autumn Wind Apartments has the second lowest priced unit, which is a 2 Beds apartment currently listed from $1,442. Here are the most affordable Downtown Winchester apartments for rent in Winchester, VA:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| North Winchester Apartments | One Bedroom | 1BR,1BA | $1,050 |
| Autumn Wind Apartments | The Shenandoah | 2BR,2BA | $1,442 |
| Blue Ridge Apartments | 2 Bedroom 1 Bath Woodstock - Reno | 2BR,1BA | $1,450 |
| Fort Collier Terrace | 2 Beds 1.5 Baths | 2BR,1BA | $1,695 |
| The Local | The Graduate | 1BR,1BA | $1,700 |
Best Value Apartments for Rent in Downtown Winchester, VA
As of November 06, 2025 the best value apartment in the Downtown Winchester area is the $1.80 price per square foot Hollingsworth Model at The Lofts at Jubal Square in the in the Park Place neighborhood starting from $2,607. The second greatest value Downtown Winchester apartment is the The Shenandoah Model at Stuart Hill starting at $2,200 with a $1.70 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. |
|---|---|---|---|
| The Lofts at Jubal Square | Hollingsworth | 3BR,2BA | $1.80 |
| Stuart Hill | The Shenandoah | 3BR,2BA | $1.70 |
| 446 N Loudoun St, Unit 1 | 446 N Loudoun St | 3BR,1BA | $1.58 |
| CEDAR HILL APARTMENTS | 2 BEDROOM 2 BATH with DEN | 3BR,2BA | $1.52 |
| Autumn Wind Apartments | The Shenandoah | 2BR,2BA | $1.46 |
| Fort Collier Terrace | 2 Beds 1.5 Baths | 2BR,1.5BA | $1.88 |
| North Winchester Apartments | Two Bedroom | 2BR,2BA | $1.47 |
| 111 E Monmouth St, Unit Downstairs Unit | 111 E Monmouth St | 2BR,1BA | $1.59 |
| Blue Ridge Apartments | 2 Bedroom 1 Bath Woodstock - Reno | 2BR,1BA | $1.86 |
| 342 Fairmont Ave, Apt 5, Unit #5 FULLY FURNISHED RENTAL Retro Loves Company | 342 Fairmont Ave, Apt 5 | 1BR,1BA | $2.62 |
Apartment Common Area Rules: What Renters Need to Know
From the lounge to the laundry room, understand your rights and responsibilities in shared apartment spaces. Get tips on pet rules, noise, and security.
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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 ArticleThe 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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Pet Friendly LifestyleDowntown Winchester, Winchester, VA
Ranked #4
Among cities in Virginia for Apartment listings with Pet Friendly Amenities.
Pet Friendliness Lifestyle Score
3.0Pet Friendly
Getting Around the Downtown Winchester Neighborhood in Winchester, VA
Walk Score®
79 / 100
Very Walkable
Most errands can be accomplished on foot
Bike Score®
49 / 100
Somewhat Bikeable
Minimal bike infrastructure
What Are Walk Score®, Transit Score®, and Bike Score® Ratings?
- Walk Score® measures the walkability of any address.
- Transit Score® measures access to public transit.
- Bike Score® measures the bikeability of any address.
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 North Winchester Apartments which is listed at $1,050, while the average apartment in Downtown Winchester costs $2,087.
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 2 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 $213 which is $1,874 cheaper than the average rent for all rentals in Downtown Winchester.
Expert Rental Resources
Helpful Apartment Articles, How-To's and Tips
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.
Apartment Common Area Rules: What Renters Need to Know
Written by: Christine Leonard, Esq.
Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.
How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!
The Rental Move-In Inspection Checklist: A Guide for Renters
Written by: Trey Huguley
The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Written by: Christine Leonard, Esq.
For many people, obstacles can arise during the rental application process for a variety of issues.