37+ Private Villas and Holiday Rentals in Winchester |
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  3. Lexington
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Winchester Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Winchester

Discover more than 37 vacation rentals available in Winchester. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Winchester.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Winchester, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Winchester. On average, places to stay near Winchester offer 527.14 ft², with nightly prices averaging US $160.

With Casai, finding and comparing holiday rentals in Winchester is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in Winchester

Type Count
Vacation Homes 15
Holiday Apartments 4

Use these Quick Filters to Find a Holiday Rental in Winchester

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Winchester.

Weather in Winchester, KY

View the weather forecast for Winchester before booking your Winchester Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Winchester, KY

Casai offers a large selection of top attractions around Winchester . Research things to do on your vacation before you visit Winchester.


Clark Regional Medical Center
Bluegrass Heritage Museum
Lykins Park
Community Park
Southwind Golf Course
Cassell Creek Golf Course
Rupp Arena
University of Kentucky
Kentucky Horse Park
Red River Gorge
Keeneland Racing Course
Fayette Mall
Kroger Field
University of Kentucky Albert B. Chandler Hospital
Natural Bridge State Park
The Mall At Lexington Green
Lexington Opera House
Lexington Convention Center
Eastern Kentucky University
Hamburg Place

Other Places to Stay in Winchester, KY


Clark County 39 Properties
Cassell Creek Golf Course 31 Properties
Southwind Golf Course 29 Properties
Bluegrass Heritage Museum 28 Properties
Lykins Park 27 Properties
Community Park 27 Properties
Clark Regional Medical Center 27 Properties

Frequently Asked Questions About Winchester?

What are the top holiday rentals in Winchester?

With numerous options available in Winchester, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Winchester:

How many Casai.nz holiday rentals are available in Winchester?

As of 2025, Casai boasts over 37 properties listed in the Winchester area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Winchester.


People Also Ask

There are 37 Winchester, KY Holiday Rentals

Recently Booked Holiday Rentals in Winchester