
Cheap Apartments for Rent in Winchester, KY from $500 (8 Rentals)
Search the lowest-cost Apartments available for rent right now in Winchester.


Studio 28 Apartments

Atrium Townhomes

Chatham Townhomes
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.

The Dawn Run Apartments

Raintree Apartments

Polo Club Park - Senior/Affordable Housing

Richwood Bend - Affordable Housing
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.
Winchester, KY Local Guide

How much does it cost to rent an apartment in Winchester?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Winchester Studio Apartments | $934 | $625 | $1,183 |
| Winchester 1 Bedroom Apartments | $1,312 | $800 | $2,847 |
| Winchester 2 Bedroom Apartments | $1,534 | $899 | $2,441 |
| Winchester 3 Bedroom Apartments | $1,894 | $1,020 | $3,301 |
| Winchester 4 Bedroom Apartments | $1,750 | $1,750 | $1,750 |
Browse Top Apartments in Winchester
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Winchester, KY Local Guide
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Cheapest Available Winchester Apartments for Rent and Nearby
 The cheapest available apartment rental in Winchester, KY is a 1 Bed unit found at Raintree Apartments in the Boone Creek neighborhood priced from $823. Studio 28 Apartments has the second lowest priced unit, which is a Studio apartment currently listed from $899. Here is today’s list of the most affordable Winchester apartments for rent:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Raintree Apartments | Willow - A1 | 1BR,1BA | $823 |
| Studio 28 Apartments | 0BR/1.0BA | Studio,1BA | $899 |
| The Dawn Run Apartments | 2x1 SM | 2BR,1BA | $920 |
Best Value Apartments for Rent in Winchester, KY and Nearby
As of February 28, 2026 the best value apartment in the Winchester area is the $1.40 price per square foot Three Bedroom 2 Bath Cottage Home Model at Legacy Lake Apartments in the starting from $2,100. The second greatest value Winchester apartment is the 3 Bedroom 2.5 Bath Model at The Pines starting at $1,500 with a $1.07 price per square foot in the Boone Creek neighborhood. Here is today’s list of the best values for Winchester apartments based on price per square foot:
| Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| Legacy Lake Apartments | Three Bedroom 2 Bath Cottage Home | 3BR,2BA | $1.40 |
| The Pines | 3 Bedroom 2.5 Bath | 3BR,2.5BA | $1.07 |
| Hamburg Farms | B3 Burton - 2 Bedroom, 1.5 Bathroom | 2BR,1.5BA | $1.23 |
| The Lofts at Winchester! 2 BR, 1 Bath, Off-Street Parking, Small Pets Ok! | 3BR/1.0BA | 3BR,1BA | $1.14 |
| Williams Estates Apartments | Two Bedroom | 2BR,1BA | $1.14 |
| Parkside Heights | 1B 1B | 1BR,1BA | $1.48 |
| Gleneagles | Two Bedroom | 2BR,2BA | $1.33 |
| The Dawn Run Apartments | 2x1 SM | 2BR,1BA | $1.08 |
| Summit Apartments | 2 BD/1.5 BA | 2BR,1.5BA | $1.30 |
| Prime Hamburg Apartments | Elite 1 BR | 1BR,1BA | $1.29 |
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.
Read ArticleThe Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.
Read ArticleCash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.
Read ArticleQuick 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.
Best Local Schools in Winchester, KY
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Remember the 3 Rules of Real Estate:Location, Location, Location!
Explore Winchester, KY Rentals by Map
See the most popular apartments and homes in Winchester, KY
Frequently Asked Questions about Cheap Winchester Apartments
What is the Cheapest Studio apartment in Winchester?
Currently the most affordable Cheap Studio Apartment in Winchester is at Studio 28 Apartments listed at $899.
How much is rent for a Cheap One Bedroom Winchester Apartment?
The lowest price for a Cheap One Bedroom Winchester Apartment is $823 at Raintree Apartments.
What is the lowest price for a Cheap Two Bedroom Winchester Apartment for rent?
Today's best deal for a Cheap Two Bedroom Apartment in Winchester is starting from $920 at The Dawn Run Apartments.
What is the most affordable Winchester Three Bedroom Apartment?
The best deal on a cheap Winchester Three Bedroom Apartment rental is at The Lofts at Winchester! 2 BR, 1 Bath, Off-Street Parking, Small Pets Ok! and starts from $1,249.
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

A Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent in Lexington
Written by: Catrina Cowart
Hi, I'm Catrina, your ApartmentHomeLiving.com Local Expert for Lexington, Kentucky, and I'm happy to talk to you about some of the neighborhoods that I've found to be particularly charming in this small city.

Maximizing Your Refund: Essential Tax Tips for Renters
Written by: Christine Leonard, Esq.
Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.

18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Written by: Lauren Harrington
Renting your next home can feel thrilling and overwhelming at the same time.

A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment
Written by: Bob Mallory
Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.