Cheap Apartments for Rent in the Old Town Neighborhood of Winchester, VA from $1,000 (16 Rentals)

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Search the lowest-cost Apartments available for rent right now in the Old Town area of Winchester.

property at 374 Woodstock Ln

374 Woodstock Ln

WinchesterVA22601
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Raleigh Court
2 Bedroom Apartments

Raleigh Court

1 Raleigh CtWinchester, VA 22601
  • Utilities Included
Showing Results 1-16, Page 1 of 1

Old Town, Winchester, VA Local Guide

Best Value Apartments for Rent in Old Town, VA

As of June 28, 2025 the best value apartment in the Old Town area is the $1.56 price per square foot 542 N Loudoun St Model at 542 N Loudoun St, Unit B in the in the Historic District neighborhood starting from $1,400. The second greatest value Old Town apartment is the 342 Fairmont Ave, Apt 5 Model at 342 Fairmont Ave, Apt 5, Unit #5 FULLY FURNISHED RENTAL Retro Loves Company starting at $1,700 with a $2.62 price per square foot in the Park Place neighborhood. Here is today’s list of the best values for Old Town apartments based on price per square foot:

Apartment ListingModel NameBed/BathPrice Per Sq.Ft.
542 N Loudoun St, Unit B542 N Loudoun St2BR,1BA$1.56
342 Fairmont Ave, Apt 5, Unit #5 FULLY FURNISHED RENTAL Retro Loves Company342 Fairmont Ave, Apt 51BR,1BA$2.62

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Pet Friendly Lifestyle
Old Town, Winchester, VA

Ranked #7

Among neighborhoods in Winchester, VA for Apartment listings with Pet Friendly Amenities

Pet Friendliness Lifestyle Score

2.5
Pet Friendly

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Best Local Schools in
Old Town, Winchester, VA

School data provided by Great Schools

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.

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Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

Written by: Cheryl Bowman

A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.

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The Art of the Rental Viewing: What to look for during a property tour

Written by: Marie Brown

You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.

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Know Your Budget: Calculating What You Can Realistically Afford When Renting

Written by: Lauren Harrington

Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.

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The Freedom of Short-Term Leases: Exploring the Advantages for Renters

Written by: Bobbi Jackson

If you’re looking to relocate right now, a popular solution that may best fit your current rental needs is a short-term lease.