Homes for Rent in the Old Town Neighborhood of Winchester, VA Under $2,000 (27 Rentals)

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property at 316 Fairview Ave

$1,700

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,700

Total Monthly Price
$1,700

2 Bedroom, 1 Bath Townhome for Rent

Available Now

316 Fairview Ave

WinchesterVA22601
property at 5 E Pall Mall St

$1,100

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,100

Total Monthly Price
$1,100

2 Bedroom, 1 Bath Townhome for Rent

Available Now

5 E Pall Mall St, Unit 7

5 E Pall Mall St
WinchesterVA22601
property at 553 Highland Ave

$1,950

Total Monthly Price

Total Monthly Price

Base Rent
$1,950

Total Monthly Price
$1,950

3 Bedroom, 2 Bath Home for Rent

Available Now

553 Highland Ave

WinchesterVA22601
property at 31 E Germain St

$1,750

Total Monthly Price

Total Monthly Price

Base Rent
$1,750

Total Monthly Price
$1,750

2 Bedroom, 2 Bath Home for Rent

Available Now

31 E Germain 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.

property at 265 Opequon Ave

$1,749

Total Monthly Price

Total Monthly Price

Base Rent
$1,749

Total Monthly Price
$1,749

3 Bedroom, 1 Bath Home for Rent

Available Now

265 Opequon Ave

WinchesterVA22601
property at 1112 Opequon Ave

$1,700

Total Monthly Price

Total Monthly Price

Base Rent
$1,700

Total Monthly Price
$1,700

3 Bedroom, 1 Bath Home for Rent

Available Now

1112 Opequon Ave

WinchesterVA22601
property at 668 Virginia Ave

$1,695

Total Monthly Price

Total Monthly Price

Base Rent
$1,695

Total Monthly Price
$1,695

3 Bedroom, 1 Bath Townhome for Rent

Available Sep 1

668 Virginia Ave

WinchesterVA22601
property at 235 Millwood Ave

$1,600

Total Monthly Price

Total Monthly Price

Base Rent
$1,600

Total Monthly Price
$1,600

2 Bedroom, 1.5 Bath Home for Rent

Available Now

235 Millwood Ave

WinchesterVA22601
property at 1839 Henry Ave

$1,600

Total Monthly Price

Total Monthly Price

Base Rent
$1,600

Total Monthly Price
$1,600

2 Bedroom, 1.5 Bath Townhome for Rent

Available Now

1839 Henry Ave

WinchesterVA22601
property at 30 W Germain St

$1,600

Total Monthly Price

Total Monthly Price

Base Rent
$1,600

Total Monthly Price
$1,600

1 Bedroom, 1 Bath Townhome for Rent

Available Now

30 W Germain St

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.

property at 619 S Cameron St

$1,600

Total Monthly Price

Total Monthly Price

Base Rent
$1,600

Total Monthly Price
$1,600

1 Bedroom, 1 Bath Townhome for Rent

Available Now

619 S Cameron St

WinchesterVA22601
property at 26 E Pall Mall St

$1,575

Total Monthly Price

Total Monthly Price

Base Rent
$1,575

Total Monthly Price
$1,575

2 Bedroom, 2 Bath Home for Rent

Available Now

26 E Pall Mall St

WinchesterVA22601
property at 527 Gray Ave

$1,550

Total Monthly Price

Total Monthly Price

Base Rent
$1,550

Total Monthly Price
$1,550

2 Bedroom, 1.5 Bath Townhome for Rent

Available Now

527 Gray Ave

WinchesterVA22601
property at 502 N Loudoun St

$1,495

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,495

Total Monthly Price
$1,495

2 Bedroom, 1 Bath Townhome for Rent

Available Sep 1

502 N Loudoun St

WinchesterVA22601
property at 1001 S Cameron St

$1,395

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,395

Total Monthly Price
$1,395

3 Bedroom, 1 Bath Home for Rent

Available Now

1001 S Cameron St

WinchesterVA22601
property at 346 Gray Ave

$1,395

Total Monthly Price

Total Monthly Price

Base Rent
$1,395

Total Monthly Price
$1,395

3 Bedroom, 1 Bath Home for Rent

Available Now

346 Gray Ave

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.

property at 305 S Kent St

$1,395

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,395

Total Monthly Price
$1,395

2 Bedroom, 1 Bath Townhome for Rent

Available Oct 1

305 S Kent St

WinchesterVA22601
property at 221 Baker St

$1,395

Total Monthly Price

Total Monthly Price

Base Rent
$1,395

Total Monthly Price
$1,395

2 Bedroom, 1 Bath Home for Rent

Available Now

221 Baker St

WinchesterVA22601
property at 222 E Whitlock Ave

$1,350

Total Monthly Price

Total Monthly Price

Base Rent
$1,350

Total Monthly Price
$1,350

3 Bedroom, 1 Bath Townhome for Rent

Available Now

222 E Whitlock Ave

WinchesterVA22601
property at 204 E Whitlock Ave

$1,250

Total Monthly Price

Total Monthly Price

Base Rent
$1,250

Total Monthly Price
$1,250

2 Bedroom, 1 Bath Townhome for Rent

Available Now

204 E Whitlock Ave

WinchesterVA22601
property at 552 Fremont St

$1,045

Total Monthly Price

Total Monthly Price

Base Rent
$1,045

Total Monthly Price
$1,045

2 Bedroom, 1 Bath Condo for Rent

Available Now

552 Fremont St

WinchesterVA22601
property at 550 N Loudoun St

$1,495

Total Monthly Price

Total Monthly Price

Base Rent
$1,495

Total Monthly Price
$1,495

1 Bedroom, 1 Bath Condo for Rent

Available Now

550 N Loudoun St, Unit 1

550 N Loudoun 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.

property at 619 S Cameron St

$1,800

Total Monthly Price

Total Monthly Price

Base Rent
$1,800

Total Monthly Price
$1,800

1 Bedroom, 1 Bath Condo for Rent

Available Now

619 S Cameron St, Unit 2

619 S Cameron St
WinchesterVA22601
property at 21 S Stewart St

$1,500

Total Monthly Price

Total Monthly Price

Base Rent
$1,500

Total Monthly Price
$1,500

2 Bedroom, 1 Bath Home for Rent

Available Now

21 S Stewart St

WinchesterVA22601
property at 21 S Stewart St

$1,900

Total Monthly Price

Total Monthly Price

Base Rent
$1,900

Total Monthly Price
$1,900

2 Bedroom, 2 Bath Condo for Rent

Available Now

21 S Stewart St, Unit 4

21 S Stewart St
WinchesterVA22601

Old Town, Winchester, VA Local Guide

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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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.

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Pet Friendly Lifestyle
Old Town, Winchester, VA

Ranked #7

Among cities in Virginia for Apartment listings with Pet Friendly Amenities.

Pet Friendliness Lifestyle Score

2.5
Pet Friendly

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Frequently Asked Questions about Old Town

What type of rentals are currently available in Old Town?

There are currently 68 Apartments for Rent in Old Town, VA with pricing that ranges from $995 to $2,600. There are also 34 Single Family Homes for rent, Condos, and Townhome rentals currently available in Old Town ranging from $750 to $2,525.

What is the current price range for Rental Homes in Old Town?

Today's rental pricing for Homes for Rent, Condos and Townhomes in Old Town ranges from $750 to $2,525 with an average monthly rent of $1,701.

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

decorative image for Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags   article

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.

decorative image for First Apartment Regrets: Real Renters Share What They'd Do Differently article

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.

decorative image for Renters Insurance 101: What It Is, What It Covers, and Why You Need It article

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.

decorative image for Apartment Occupancy Rates: Renter Attraction vs Renter Retention   article

Apartment Occupancy Rates: Renter Attraction vs Renter Retention

Written by: Robin Stewart

There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.