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Find 5 Star Hotels in Winchester, KY from $117

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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.

Learn more about Winchester

Stroll through charming downtown streets lined with local shops and eateries. Tee off at Cassell Creek or Southwind Golf Course, then explore local history at the Bluegrass Heritage Museum.

Thanks to my friend of mine who's recommended me to this spot easy hike short walk to get there
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Top Winchester Hotel Reviews

Find out more about Winchester

Ready to experience the next standard in luxury? We know you're thinking about it. Add further luxury on your next trip to Winchester by treating yourself to the best of the best when it comes to accommodation. It's an ideal combination. There's no reason to delay a getaway to Winchester any longer. You'll join the multitudes of vacationers who have made Winchester so fashionable recently. We should also mention, the hotels in this area are known for guest services, so you know you'll want for nothing during your getaway. What are you waiting for? Book one of Expedia's luxurious 5-star hotels in Winchester and get ready to enjoy the getaway of a lifetime.

5-Star Hotels in Winchester

Don't be afraid to live the high life while you're on vacation. Exceptional customer care, granite-tiled bathrooms, and rejuvenating spa offerings are waiting for you. You're sure to find exactly the accommodation you need. Besides that, you'll find that these hotels are kept in great shape and provide a fine place to lay your head at night. How do you want to relax? A mud wrap treatment that will leave you feeling outstanding? 24-hour room service, so you can order that filet mignon in the wee hours of the morning? A full-body massage to help your cares fall away? Don't want to take our word for it? Explore the review section and see what previous visitors have said. You're sure to find exactly what you're looking for!

Yearning for experiences outside your hotel room? You're in luck. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. Whatever you plan to do, the 5-star hotels in Winchester are waiting for you to rest up after a busy day.

Your Getaway Starts Today

The results are in, and Winchester 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. It's time to indulge yourself -- Expedia can help you land a great deal on accommodation. Choose one of Expedia's Winchester 5-star hotels today and dive into in the lap of luxury tomorrow.

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Winchester?
The amount you pay for a 5-star hotel in Winchester can vary depending on the time of year you travel and how long you plan to be away, among a number of factors. Use our price per night filter and other search tools to land the best rate on an indulgent stay.

  • Search for the lowest price per night from $117

What makes a hotel 5 stars in Winchester?
From fine dining venues and all-day fitness centers to swimming pools and superior bedding, the 5-star experience in Winchester is all about luxury and relaxation. But it requires more than just upscale perks to receive a 5-star rating. Stays must also offer superior services like in-room beauty treatments, on-site laundry and dry cleaning and concierge services.
Are there any 5-star all-inclusive resorts in Winchester?
Use our filters to find a high-end retreat in Winchester where most of what you need is included. From there, narrow down your results for resorts that have a 5-star rating and are described as "All inclusive." The most important thing to look forward to at these stays? Pure indulgence and relaxation.

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