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!

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

Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!
Randolph Inn and Suites

Randolph Inn and Suites

2.5 out of 5
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

Randolph Inn and Suites
Baymont by Wyndham Richmond I-70

Baymont by Wyndham Richmond I-70

2.5 out of 5
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

Baymont by Wyndham Richmond I-70
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.