Winchester Holidays
Book a Hotel + Flight or Car together to unlock savings
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
Randolph Inn and Suites
890 E Washington Winchester IN
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (245 reviews)
Breakfast was good.the staff very friendly and the other hotel guest very friendly
Reviewed on 28 Oct 2025
Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA
Winchester IN
9.6/10 Exceptional! (183 reviews)
This was a beautiful home was enjoyed by all. The amenities are great, Walmart is right around the corner, the pool was warm and Ted was very welcoming. We were disappointed to learn that the hot tub had been closed early due to cold weather, but that don’t stop us from having a great time! We would ...
Reviewed on 16 Dec 2025
Baymont by Wyndham Richmond I-70
912 Mendleson Dr Richmond IN
Fully refundableReserve now, pay when you stay
The price is AU$112 per night from 25 Jan to 26 Jan
AU$112
25 Jan - 26 Jan 2026
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
Debbie was at the front desk and she was awesome ! Friendly, fast and courteous !
Reviewed on 20 Dec 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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
