
Winchester Holidays
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Your Winchester Holiday
The vibrant city of Winchester is calling your name. Discover its hot spots and hidden treasures with a Winchester holiday package that's customised to you. If your trip to Winchester includes some sightseeing, don't miss popular attractions like Winchester Speedway, Winchester Golf Club and Historic Shopping & Dining District of Winchester, Indiana. Expedia will help you escape the everyday. Tailor your holiday to Winchester to suit your style of travel, whatever that may look like.
Winchester Holiday
Winchester Essential Information
Language | English |
---|---|
Currency | U.S dollars |
Population | 4,800 |
Max Temp Winter | 2ºC |
Max Temp Summer | 27ºC |
Top Sights | Winchester Speedway, Winchester Golf Club and Historic Shopping & Dining District of Winchester, Indiana |
Our pick of the best Winchester Hotel Deals

Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!
Winchester
9.6/10 Exceptional! (180 reviews)
"House and backyard is huge! We absolutely enjoyed being outdoors with the kids, the indoor pool came in clutch while the weather was in the cooler side during our stay. Ted was readily available and provided clear communication."
Reviewed on 24 Sept 2025

Randolph Inn and Suites
890 E Washington, Winchester, IN
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (237 reviews)
"Great people working for our stay and was very friendly."
Reviewed on 15 Sept 2025

Baymont by Wyndham Richmond I-70
912 Mendleson Dr, Richmond, IN
Fully refundableReserve now, pay when you stay
The price is AU$130 per night from 19 Oct to 20 Oct
AU$130
19 Oct - 20 Oct
includes taxes & fees
8.2/10 Very Good! (1,013 reviews)
"Arrived at hotel late and our room had been double booked, front desk clerk quickly took care of the problem. Upgraded us to a suite, he was very efficient and pleasant. The suite's shower was awesome, bed was comfortable, nice breakfast in the morning."
Reviewed on 8 Oct 2025
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.