377 National Ave
WinchesterVA22601
Cheap Apartments for Rent in the Old Town Neighborhood of Winchester, VA from $1,095 (24 Rentals)
Search the lowest-cost Apartments available for rent right now in the Old Town area of Winchester.
406 N Loudoun St
WinchesterVA22601
1704 Roberts St
WinchesterVA22601
22 Peyton St
WinchesterVA22601
129 Holiday Dr
WinchesterVA22601
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$1,300
Total Monthly Price
Base Rent$1,300
Total Monthly Price$1,300
318 S Cameron St, Unit Apt A
318 S Cameron StWinchester, VA 22601
4 W Cork St
WinchesterVA22601
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$1,500
Total Monthly Price
Base Rent$1,500
Total Monthly Price$1,500
115 S Loudoun St, Unit 1
115 S Loudoun StWinchester, VA 22601
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.
115 S Loudoun St
WinchesterVA22601
21-23-23 S Stewart St
WinchesterVA22601
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2 Bedroom Apartments
22 Peyton St
22 Peyton StWinchester, VA 22601
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1 to 3 Bedroom Apartments
ZeroPak Apartments
570 N Cameron StWinchester, VA 22601
204 E Whitlock Ave
WinchesterVA22601
714 S Cameron St
WinchesterVA22601
1001 S Cameron St
WinchesterVA22601
346 Gray Ave
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.
305 S Kent St
WinchesterVA22601
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2 Bedroom Apartments
Raleigh Court
1 Raleigh CtWinchester, VA 22601
131 S Purcell Ave
WinchesterVA22601
230 E Whitlock Ave
WinchesterVA22601
502 N Loudoun St
WinchesterVA22601
21 S Stewart St
WinchesterVA22601
619 S Cameron St
WinchesterVA22601
31 Avon Ct
WinchesterVA22601
How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.
Showing Results 1-24, Page 1 of 1
Old Town, Winchester, VA Local Guide
How much does it cost to rent an apartment in Old Town?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Old Town Studio Apartments | $1,700 | $1,700 | $1,700 |
| Old Town 1 Bedroom Apartments | $1,833 | $1,095 | $2,200 |
| Old Town 2 Bedroom Apartments | $1,895 | $1,150 | $2,600 |
| Old Town 3 Bedroom Apartments | $2,025 | $1,900 | $2,150 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Apartments in this Neighborhood
There are currently 24 rentals with your search options within a 1 mile radius of the Old Town Neighborhood of Winchester, VA.
See all Apartments in WinchesterExplore Winchester
Old Town, Winchester, VA Local Guide
- Nearby Winchester neighborhoods
- Nearby Cities
- ZIP codes
- Local Counties
Best Value Apartments for Rent in Old Town, VA
As of September 19, 2026 the best value apartment in the Old Town area is the $1.27 price per square foot 308 W Boscawen St Model at 308 W Boscawen St, Unit 308 W Boscawen Street Apt 2 in the Park Place neighborhood starting from $1,900. The second greatest value Old Town apartment is the 21 N Braddock St Model at 21 N Braddock St, Unit #3 in the Park Place neighborhood starting at $1,600 with a $1.28 price per square foot. Here is today’s list of the best values for Old Town 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 | $1.27 |
| 21 N Braddock St, Unit #3 | 21 N Braddock St | 2BR, 1BA | $1.28 |
| 318 S Cameron St, Unit Apt A | 318 S Cameron St | 2BR, 1BA | $1.44 |
| 342 Fairmont Ave, Unit Apt 3 | 342 Fairmont Ave | 2BR, 1BA | $2.47 |
| 115 S Loudoun St, Unit 1 | 115 S Loudoun St | 1BR, 1BA | $2.14 |
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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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 LifestyleOld Town, Winchester, VA
Ranked #8
Among cities in Virginia for Apartment listings with Pet Friendly Amenities.
Pet Friendliness Lifestyle Score
2.5Pet Friendly
Best Local Schools in Old Town, Winchester, VA
Daniel Morgan Middle School
Winchester City Public Schools
Public School - Grades 6-8 (642)
4 out of 10
School data provided by Great Schools
Frequently Asked Questions about Cheap Old Town Apartments
What is the lowest price for a Cheap Two Bedroom Old Town Apartment for rent?
Today's best deal for a Cheap Two Bedroom Apartment in Old Town is starting from $1,150 at 22 Peyton 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
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.
How Commercial-to-Residential Property Conversions Help the Housing Crisis
Written by: Robin Stewart
Many housing markets throughout America share a common complaint: a lack of affordable rental properties.
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.