Winchester
Travel Guide
Visit Winchester
Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA
Winchester
Book a stay at this family-friendly vacation home in Winchester. Enjoy free WiFi, private pools, and a water park. Popular attractions Winchester Golf Club and ...
9.6/10 Exceptional! (181 reviews)
Very nice, large, and clean. Plenty of space for everyone! Only downfall house is very musty especially the basement and chlorine smell from the pool. Cost was a bit high for 10 adults and 2 children for 2 nights was almost 5000 but in then end it was worth it. Hosts are very lovely and great communication. ...
Reviewed on 29 Sept 2025
Randolph Inn and Suites
890 E Washington, Winchester, IN
Stay at this hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the property condition in our reviews. Popular attractions ...
8.8/10 Excellent! (240 reviews)
Breakfast was good.the staff very friendly and the other hotel guest very friendly
Reviewed on 28 Oct 2025
Baymont by Wyndham Richmond I-70
912 Mendleson Dr, Richmond, IN
The price is HK$587 per night from 2 Nov to 3 Nov
HK$587
HK$658 total
2 Nov - 3 Nov
includes taxes & fees
Stay at this inn in Richmond. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
8.2/10 Very Good! (1,005 reviews)
Breakfast was great, there was a staff member who made us eggs to order, along with the buffet and the waffle maker. Weekend in super late (like 2am) and there was a desk attendant readily available. Room was clean and quiet.
Reviewed on 24 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.
Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA
Winchester
Book a stay at this family-friendly vacation home in Winchester. Enjoy free WiFi, private pools, and a water park. Popular attractions Winchester Golf Club and ...
9.6/10 Exceptional! (181 reviews)
Very nice, large, and clean. Plenty of space for everyone! Only downfall house is very musty especially the basement and chlorine smell from the pool. Cost was a bit high for 10 adults and 2 children for 2 nights was almost 5000 but in then end it was worth it. Hosts are very lovely and great communication. ...
Reviewed on 29 Sept 2025
Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy
Fort recovery
Book a stay at this family-friendly vacation home in Fort Recovery. Enjoy private pools, a fitness center, and a garden. Our guests praise the property condition ...
10/10 Exceptional! (201 reviews)
The place is set up great for our extended family vacation. We have enough space to hang out or play in the gym or pool!
Reviewed on 20 Oct 2025
Quaker Hill Cottage on gated estate with fire pit & hiking trails
Richmond
Stay at this cottage in Richmond. Enjoy laundry facilities, patios, and air conditioning. Popular attractions Middlefork Reservoir Park and Depot District are ...
9.6/10 Exceptional! (26 reviews)
Check in was easy but there were no check out instructions so I just kind of did similar to check in with key. Nice place. Lots of room for my daughter’s sleepover but only one tv in the whole house which was a bummer. Also stairs could be safety hazard for some. Was difficult taking a toddler up ...
Reviewed on 10 Aug 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.
Popular places to visit
Winchester Speedway
Catch an event at Winchester Speedway during your trip to Winchester.
Winchester Golf Club
Enjoy a round of golf in Winchester at Winchester Golf Club.
Randolph County Courthouse
After visiting Randolph County Courthouse, make a plan to see the other sights and activities in Winchester.
