Winchester Hotel Guide - 5 Stars Hotels in Winchester, Lexington

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Check availability on Winchester 5 Star Hotels

Tonight
2 May - 3 May
Tomorrow
3 May - 4 May
Next weekend
8 May - 10 May
In two weeks
15 May - 17 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 Rp2.048.367 per night from 17 May to 18 May
Rp2.048.367
Rp2.377.423 total
17 May - 18 May
includes taxes & fees
8.8/10 Excellent! (1,000 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 city centre 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?
There are various pricing options for a 5-star hotel in Winchester on Expedia. How much you'll pay will depend on when you plan to travel, length of stay and other factors. Compare all of the available accommodation for your preferred dates and use our pricing and other filters to find the perfect upscale stay.

  • Search for the lowest price per night from Rp2.377.423

What makes a hotel 5 stars in Winchester?
Flawless guest service is the hallmark of every 5-star hotel in Winchester. From the minute you step through the door, staff cater to your every need, whether arranging customised tours or providing a nightly turn-down service. Plus, hotels must offer superior conveniences to obtain a 5-star rating. These can include luxury bathrobes, a wellness centre, swimming pools, gastronomic kitchens and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Winchester?
Expedia's filter tool is the quickest way to narrow down what you want. Select "5-star" and "All inclusive" to show the finest properties in Winchester where your meals, accommodation, entertainment and activities are included in the upfront price. At these retreats, your holiday is pure leisure from the moment you enter the lobby.