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Luxury Hotels & Resorts in Winchester from NZ$137

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Check availability on Winchester Luxury Hotels

Tonight
30 Dec - 31 Dec
Tomorrow
31 Dec - 1 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Winchester luxury hotels

Seasonal outdoor pool
Best Western Winchester Hotel

Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very good, (1000)
"Clean room, friendly and fast check in service and had a great nights sleep "
United States
Cynthia
The price is NZ$137
includes taxes & fees
4 Jan - 5 Jan 2026
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.
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Top Winchester Hotel Reviews

Spark by Hilton Lexington Hamburg

Spark by Hilton Lexington Hamburg

10/10 Excellent
"Not enough menu only had cereal and bagel "
kyong 1-night trip
Posted 7 days ago
Spark by Hilton Lexington Hamburg
21c Museum Hotel Lexington

21c Museum Hotel Lexington

10/10 Excellent
"Great hotel and location. "
Tammy 1-night trip
Posted 2 weeks ago
21c Museum Hotel Lexington

Frequently asked questions

Are you searching for a great accommodation for your luxury holiday in Winchester?
Use Expedia to help you arrange a flight to Lexington, KY (LEX-Blue Grass) 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'd like 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 temperature of 22°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Winchester is 1426 mm.
What's there to see and do in Winchester?
Experience Winchester and visit Bluegrass Heritage Museum, Winchester Opera House and Clark County Courthouse. If you have extra time while you're in the area, you might want to see College Park and Clark County Public Library.

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