Winchester Holidays
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Winchester Holiday
Our pick of the best Winchester Hotel Deals
Randolph Inn and Suites
890 E Washington Winchester IN
Fully refundableReserve now, pay when you stay
The price is NZ$186 per night from 4 May to 5 May
NZ$186
4 May - 5 May
includes taxes & fees
9/10 Wonderful! (253 reviews)
There are 2 properties, a motel and a hotel. This is NOT clear when you are making a reservation thru Expedia. The motel is older. The beds are super low. The shower is small. You have to drive to the hotel to eat breakfast and check in/out. The breakfast was good with hot items. The pool was closed ...
Reviewed on 30 Mar 2026
Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA
Winchester IN
9.8/10 Exceptional! (200 reviews)
We have rented large reunion places before. This one looks better online than it was in person. Functionally everything worked, but the decor and furniture were highly dated, hence four stars instead of five. The cleanliness was OK except in the basement, which was very dusty. We had great conversations ...
Reviewed on 8 Mar 2026
Baymont by Wyndham Richmond I-70
912 Mendleson Dr Richmond IN
Fully refundableReserve now, pay when you stay
The price is NZ$135 per night from 12 Apr to 13 Apr
NZ$135
12 Apr - 13 Apr
includes taxes & fees
8.4/10 Very Good! (1,007 reviews)
Very friendly staff and the cleanliness of the room and bathroom were exceptional.
Reviewed on 6 Apr 2026
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.
