Cheap Apartments for Rent in the Downtown Winchester Neighborhood of Winchester, VA from $800 (8 Rentals)

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

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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Pine Plaza
2 to 3 Bedroom Apartments

Pine Plaza

2237 Taft CirWinchester, VA 22601

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.

Downtown Winchester, Winchester, VA Local Guide

Cheapest Available Downtown Winchester Apartments for Rent

 

The cheapest available apartment rental in the Downtown Winchester area of Winchester, VA is a 2 Beds unit found at North Winchester Apartments priced from $1,300. Blue Ridge Apartments has the second lowest priced unit, which is a 2 Beds apartment currently listed from $1,475. Here are the most affordable Downtown Winchester apartments for rent in Winchester, VA:

Apartment ListingModel NameBed/BathPriced From
North Winchester Apartments2 Beds, 2 baths2BR,2BA$1,300
Blue Ridge Apartments2 Bedroom 1 Bath - Reno2BR,1BA$1,475
Fort Collier Terrace2 Beds 1.5 Baths2BR,1BA$1,695

Best Value Apartments for Rent in Downtown Winchester, VA

As of September 20, 2025 the best value apartment in the Downtown Winchester area is the $1.67 price per square foot Braddock Model at The Lofts at Jubal Square in the in the Park Place neighborhood starting from $2,116. The second greatest value Downtown Winchester apartment is the 446 N Loudoun St Model at 446 N Loudoun St, Unit 1 starting at $1,995 with a $1.66 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 ListingModel NameBed/BathPrice Per Sq.Ft.
The Lofts at Jubal SquareBraddock2BR,2BA$1.67
446 N Loudoun St, Unit 1446 N Loudoun St3BR,1BA$1.66
Meadow Branch Luxury ApartmentsGala1BR,1BA$2.10
Fort Collier Terrace2 Beds 1.5 Baths2BR,1.5BA$1.88
North Winchester Apartments2 Beds, 2 baths2BR,2BA$1.47
Blue Ridge Apartments2 Bedroom 1 Bath - Reno2BR,1BA$1.79
342 Fairmont Ave, Apt 5, Unit #5 FULLY FURNISHED RENTAL Retro Loves Company342 Fairmont Ave, Apt 51BR,1BA$2.62
The LocalThe Graduate1BR,1BA$2.79

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Pet Friendly Lifestyle
Downtown Winchester, Winchester, VA

Ranked #4

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

Pet Friendliness Lifestyle Score

3.5
Pet Friendly

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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

Frequently Asked Questions about Cheap Downtown Winchester Apartments

How much is rent for a Cheap One Bedroom Downtown Winchester Apartment?

The lowest price for a Cheap One Bedroom Downtown Winchester Apartment is $1,700 at The Local.

What is the lowest price for a Cheap Two Bedroom Downtown Winchester Apartment for rent?

Today's best deal for a Cheap Two Bedroom Apartment in Downtown Winchester is starting from $1,300 at North Winchester Apartments.

What is the most affordable Downtown Winchester Three Bedroom Apartment?

The best deal on a cheap Downtown Winchester Three Bedroom Apartment rental is at Fort Collier Terrace and starts from $1,795.

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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How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate! 

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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.

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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.

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The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro

Written by: Christine Leonard, Esq.

Hard truth. Moving is never easy. I’ve done it all – from local moves to cross-country relocations From packing to unpacking the last box, I have found moving to be an exhausting, expensive and stressful experience every time.