Find 5 Star Hotels in Winchester, KY from SAR 463

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Check availability on Winchester 5 Star Hotels

Tonight
26 Apr - 27 Apr
Tomorrow
27 Apr - 28 Apr
Next weekend
1 May - 3 May
In two weeks
8 May - 10 May
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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Winchester.
DoubleTree Suites by Hilton Hotel Lexington

DoubleTree Suites by Hilton Hotel Lexington

2601 Richmond Rd Lexington KY
The price is SAR 443 per night from May 17 to May 18
SAR 443
SAR 514 total
17 May - 18 May
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
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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.

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MAY 9, 2023 - WINCHESTER, KENTUCKY - aerial view of historic small town of Winchester with Town Clocktower and historic storefronts and buildings

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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 SAR 463

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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