453 Darley Creek
Mount SterlingKY40353
Cheap Homes for Rent in Winchester, KY from $800 (8 Rentals)
Search the lowest-cost Homes available for rent right now in Winchester.
39 S Highland St
WinchesterKY40391
1811 Dalton Ct
LexingtonKY40505
2901 Affirmed Ct
LexingtonKY40509
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.
408 Bainbridge Ct
LexingtonKY40509
570 Anniston Dr
LexingtonKY40505
31 Franklin Ave
WinchesterKY40391
501 Lee Ct
RichmondKY40475
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.
Showing Results 1-8, Page 1 of 1
Winchester, KY Local Guide
Aerial view of Winchester by Flickr User: kenlund is licensed under CC BY 2.0
How much does it cost to rent a home in Winchester?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Winchester 2 Bedroom Homes for Rent | $1,299 | $850 | $1,650 |
| Winchester 3 Bedroom Homes for Rent | $1,938 | $1,400 | $2,600 |
| Winchester 4 Bedroom Homes for Rent | $2,340 | $1,495 | $2,950 |
| Winchester 5 Bedroom Homes for Rent | $3,099 | $3,099 | $3,099 |
Browse Top Homes for Rent in Winchester
Explore Winchester
Winchester, KY Local Guide
- Nearby Cities
- ZIP codes
- Local Counties
- School Districts
Cheapest Available Winchester Apartments for Rent and Nearby
The cheapest available apartment rental in Winchester, KY is a 1 Bed unit found at Eastland Hills Apartments in the Liberty Area neighborhood priced from $850. The Dawn Run Apartments in the Eastland Parkway neighborhood has the second lowest priced unit, which is a 2 Beds apartment currently listed from $920. Here is today’s list of the most affordable Winchester apartments for rent:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Eastland Hills Apartments | 1 Bedroom | 1BR,1BA | $850 |
| The Dawn Run Apartments | 2x1 SM | 2BR,1BA | $920 |
| Raintree Apartments | Willow - A1 | 1BR,1BA | $985 |
Best Value Apartments for Rent in Winchester, KY and Nearby
As of July 24, 2025 the best value apartment in the Winchester area is the $1.25 price per square foot Three Bedroom Model at Garden Estates in the in the Athens Historic District neighborhood starting from $1,816. 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. |
|---|---|---|---|
| Garden Estates | Three Bedroom | 3BR,2BA | $1.25 |
| The Pines | 3 Bedroom 2.5 Bath | 3BR,2.5BA | $1.07 |
| Colts Run | Belmont - 3 Bedroom, 2 Bath (1,398 sqft.) | 3BR,2BA | $1.34 |
| Hamburg Farms | B3 Burton - 2 Bedroom, 1.5 Bathroom | 2BR,1.5BA | $1.19 |
| Brighton 3050 | 2.1/2.1G | 2BR,2BA | $1.25 |
| SPECIALS: The Reserve & Enclave at Fairholme | The Enclave | 2BR,2.5BA | $1.36 |
| 127 W Hickman St, Unit 5 | 127 W Hickman St | 1BR,1BA | $1.00 |
| Stoney Brooke Apartments | Somerset - Renovated | 2BR,1BA | $1.28 |
| Eastland Hills Apartments | 1 Bedroom | 1BR,1BA | $1.14 |
| 192 Wabash Ave | 192 Wabash Ave | Studio ,1BA | $1.00 |
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.
Let everyone know!
Do you know the Winchester area?
If you’re an expert on all things Winchester, tell us what you love (and don't) by rating it and writing a review.
Write a Review
Frequently Asked Questions about Winchester
What type of rentals are currently available in Winchester?
There are currently 64 Apartments for Rent in Winchester, KY with pricing that ranges from $600 to $3,679. There are also 36 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $850 to $3,099.
What is the current price range for Rental Homes in Winchester?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Winchester ranges from $850 to $3,099 with an average monthly rent of $1,915.
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.
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.
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.
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.
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.