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Check availability on Winchester Luxury Hotels

Top Winchester Luxury Hotels

Our top choices for Winchester luxury hotels

Best Western Winchester Hotel
Seasonal outdoor pool

Best Western Winchester Hotel

2.5 star property
8.4 out of 10, Very good, (961)
"Was very quiet, nice swimming pool and great breakfast. The staff was very friendly."
The price is CA $125
CA $138 total
includes taxes & fees
Aug 24 - Aug 25
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.

Top Winchester Hotel Reviews

Elwood Hotel & Suites

Elwood Hotel & Suites

10/10 Excellent
"A lovely hotel. great service, comfortable, nice room. Delicious breakfast and close to the University. A perfect stay"
Antony 1-night trip
Posted 18 hours ago
Elwood Hotel & Suites

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.