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Find luxury hotels in Winchester, KY

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Top Winchester Luxury Hotels

Best Western Winchester Hotel

2.5 star property
8.4 out of 10, Very Good, (979)
"Firm bed, clean room, friendly staff and adequate breakfast. "
$93 nightly
The price is $103
Oct 6 - Oct 7
Total with taxes and fees
Best Western Winchester Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find out more about Winchester

Find out more about Winchester

Winchesterand its attractions for luxury travelers

In Winchester, Kentucky, luxury travelers can indulge in a variety of upscale experiences. Begin your exploration at the historic Bluegrass Heritage Museum, where you can immerse yourself in the rich local culture and history of the region. The museum showcases unique artifacts and exhibits that tell the story of Kentucky’s bluegrass music and heritage. For those who appreciate fine dining, the nearby Glenwood Restaurant features a farm-to-table menu with exquisite, locally sourced ingredients, making every meal a memorable experience. Nature enthusiasts will enjoy a visit to the scenic Lower Howard's Creek Nature Preserve, where you can hike along tranquil trails and bask in the beauty of the lush landscapes. For a taste of local craft brews, the Country Boy Brewing offers a cozy atmosphere and is known for its innovative beers that showcase local flavors. Luxury accommodations in Winchester can be found in the charming downtown area, where boutique hotels provide personalized service and easy access to these attractions. Staying here allows you to enjoy leisurely strolls along historic streets, explore unique shops, and return to your elegant hotel for a restful evening, making your visit both comfortable and enriching.

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Frequently asked questions

Are you searching for a great accommodation for your luxury trip to Winchester?
Use Expedia to help you arrange a flight to Blue Grass Airport (LEX) airport, and then choose from a variety of places to stay that will deliver the luxury you want. Amenities are important when you plan a trip, so we make it easy to find what you want to make your stay special. If you want an upscale hotel with a spa, an indoor pool, or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Winchester offers. During your visit, you might want to enjoy the restaurants which Winchester is known for.
When can I expect good weather in Winchester?
Planning for the weather is an important factor for making your trip to Winchester a success, especially when you're splurging. The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Winchester is 56 inches.
What's there to see and do in Winchester?
Experience Winchester and visit Bluegrass Heritage Museum, Lykins Park, and Southwind Golf Course. If you have extra time while you're in the area, you might want to see Winchester Opera House and Clark County Courthouse.

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