
Cheap Apartments for Rent in the Historic District Winchester, VA from $1,000 (10 Rentals)
Search the lowest-cost Apartments available for rent right now in the Historic District area of Winchester.


1704 Roberts St
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.

208 W Boscawen St

4 W Cork St

372 Woodstock Ln

376 Woodstock Ln

382 Woodstock Ln

113 W Boscawen St

304 S Kent St
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.
Historic District, Winchester, VA Local Guide

How much does it cost to rent an apartment in Historic District?
Bedroom | Average Rent | Cheapest Rent | Highest Rent |
---|---|---|---|
Historic District Studio Apartments | $1,500 | $1,300 | $1,700 |
Historic District 1 Bedroom Apartments | $1,832 | $1,013 | $2,150 |
Historic District 2 Bedroom Apartments | $2,165 | $1,249 | $3,100 |
Historic District 3 Bedroom Apartments | $1,768 | $1,400 | $1,995 |
Browse Apartments in this Neighborhood
There are currently 10 rentals with your search options within a 1 mile radius of the Historic District Neighborhood of Winchester, VA.
See all Apartments in WinchesterExplore Winchester
Historic District, Winchester, VA Local Guide
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Best Value Apartments for Rent in Historic District, VA
As of September 20, 2025 the best value apartment in the Historic District area is the $1.66 price per square foot 446 N Loudoun St Model at 446 N Loudoun St, Unit 1 in the in the Park Place neighborhood starting from $1,995. The second greatest value Historic District 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 Historic District apartments based on price per square foot:
Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
---|---|---|---|
446 N Loudoun St, Unit 1 | 446 N Loudoun St | 3BR,1BA | $1.66 |
342 Fairmont Ave, Apt 5, Unit #5 FULLY FURNISHED RENTAL Retro Loves Company | 342 Fairmont Ave, Apt 5 | 1BR,1BA | $2.62 |
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Pet Friendly LifestyleHistoric District, Winchester, VA
Ranked #6
Among cities in Virginia for Apartment listings with Pet Friendly Amenities.
Pet Friendliness Lifestyle Score
3.0Pet Friendly
Best Local Schools in Historic District, 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.

How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!

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.

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.

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.