close
View Me
$1,600 - $1,8001 to 2 Bedroom Apartments Contact Us For Availability
Plus Fees
148 N Loudoun St
148 N Loudoun StWinchester, VA 22601
Apartments for Rent in the Old Town Neighborhood of Winchester, VA (104 Rentals)
close
View Me
$1,800 - $2,6001 to 2 Bedroom Apartments Available Nov 1
Plus Fees
210 S Cameron St
210 S Cameron StWinchester, VA 22601
close
View Me
$1,600 - $2,600Studio to 2 Bedroom Apartments Available Nov 1
Plus Fees
The Merchant Suites at 114 North Loudoun
114 N Loudoun StWinchester, VA 22601
close
View Me
$2,000
Total Monthly Price
Base Rent$2,000
Total Monthly Price$2,000
308 W Boscawen St, Unit 308 W Boscawen Street Apt 2
308 W Boscawen StWinchester, VA 22601
close
View Me
$1,700
Total Monthly Price
Base Rent$1,700
Total Monthly Price$1,700
21 N Braddock St, Unit #3
21 N Braddock StWinchester, VA 22601
close
View Me
$2,100
Total Monthly Price
Base Rent$2,100
Total Monthly Price$2,100
342 Fairmont Ave, Unit Apt 3
342 Fairmont AveWinchester, VA 22601
close
View Me
$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
316 Fairview Ave
WinchesterVA22601
close
View Me
$1,8501 Bedroom Apartments Available Now
406 N Loudoun St, Unit 1
406 N Loudoun StWinchester, VA 22601
377 National 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.
406 N Loudoun St
WinchesterVA22601
519 Amherst St
WinchesterVA22601
210 E Boscawen St
WinchesterVA22601
402 S Loudoun St
WinchesterVA22601
40 S Loudoun St
WinchesterVA22601
517 Amherst St
WinchesterVA22601
515 Amherst St
WinchesterVA22601
25 E Boscawen St
WinchesterVA22601
21-23-23 S Stewart St
WinchesterVA22601
116 N Indian Alley
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.
107 Morgan St
WinchesterVA22601
213 N Kent St
WinchesterVA22601
18 -1/2-18 1/2 Morningside Dr
WinchesterVA22601
1704 Roberts St
WinchesterVA22601
22 Peyton St
WinchesterVA22601
211 E Boscawen St
WinchesterVA22601
122 N Washington St
WinchesterVA22601
305 S Kent St
WinchesterVA22601
317 S Kent St
WinchesterVA22601
223 Baker St
WinchesterVA22601
Neighborhood & Market Insights: How to Choose the Right Area to Rent
Master your search for the perfect apartment. Location is everything. Discover how to leverage community insights, public data, and personal visits to make a fully informed decision about where to rent.
346 Gray Ave
WinchesterVA22601
619 S Cameron St
WinchesterVA22601
30 W Germain St
WinchesterVA22601
502 N Loudoun St
WinchesterVA22601
714 S Cameron St
WinchesterVA22601
26 E Pall Mall St
WinchesterVA22601
527 Gray Ave
WinchesterVA22601
332 Shawnee Ave
WinchesterVA22601
553 Highland Ave
WinchesterVA22601
1001 S Cameron St
WinchesterVA22601
The Art of the Rental Viewing: What to look for during a property tour
Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.
265 Opequon Ave
WinchesterVA22601
380 Shawnee Ave
WinchesterVA22601
668 Virginia Ave
WinchesterVA22601
131 S Purcell Ave
WinchesterVA22601
204 E Whitlock Ave
WinchesterVA22601
230 E Whitlock Ave
WinchesterVA22601
1112 Opequon Ave
WinchesterVA22601
122 Morningside Dr
WinchesterVA22601
1839 Henry Ave
WinchesterVA22601
739 S Kent St
WinchesterVA22601
Smart Renter's Guide: Calculating Affordable Rent & Housing Costs
Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.
Showing Results 1-50, Page 1 of 3
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 | $1,500 | $1,300 | $1,700 |
| Old Town 1 Bedroom Apartments | $1,817 | $1,095 | $2,200 |
| Old Town 2 Bedroom Apartments | $1,977 | $1,150 | $2,600 |
| Old Town 3 Bedroom Apartments | $1,925 | $1,625 | $2,150 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
How much does it cost to rent a home in Old Town?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| 2 Bedroom Homes | $1,543 | $1,250 | $1,900 |
| 3 Bedroom Homes | $1,772 | $1,395 | $2,525 |
| 4 Bedroom Homes | $2,297 | $2,100 | $2,495 |
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 104 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
A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back
Learn the property manager's true secrets to a zero-deduction move-out. Use this step-by-step guide on documentation, cleaning, and lease-reading to reclaim your security deposit.
Read Article
18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Tour smarter and choose with confidence. Get the essential 18 questions that reveal the truth about a rental property's maintenance, utilities, and safety.
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.
Read Article
Quick Rent Budget Calculator
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.
Let everyone know!
Do you know the Old Town area?
If you’re an expert on all things Old Town, tell us what you love (and don't) by rating it and writing a review.
Write a Review
Pet Friendly LifestyleOld Town, Winchester, VA
Ranked #7
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 Old Town
What is the current pricing and availability for apartments for rent in the Old Town area of Winchester, VA?
As of today, September 09, 2026, there are currently 104 available Old Town apartments priced from $1,095 to $2,600, with an average monthly rent of $1,870.
What is the current price range for One Bedroom Old Town Apartments for rent?
Today's rental pricing for One Bedroom Apartments in Old Town ranges from $1,095 to $2,200 with an average monthly rent of $1,817.
What does renting a Two Bedroom Apartment in Old Town cost?
The monthly rent prices of Two Bedroom Apartments currently available in Old Town range from $1,150 to $2,600. Today's average rental price for Two Bedrooms here is $1,977.
How expensive are Old Town Three Bedroom Apartments?
There are currently 9 Three Bedroom Apartments listings available in Old Town on ApartmentHomeLiving.com. The pricing ranges from $1,625 to $2,150 - averaging $1,925 for the location.
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
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.
Renters Insurance 101: What It Is, What It Covers, and Why You Need It
Written by: Robin Stewart
Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.