Title: Visit Winchester: 2026 Travel Guide for Winchester, Indiana | Expedia.com [Hotels in Winchester](https://expedia.com/Winchester-Hotels.d6046207.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.com/Winchester-Vacation-Rentals.d6046207.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.com/Cheap-Flights-To-Winchester.d6046207.Travel-Guide-Flights)[Car Rentals in Winchester](https://expedia.com/Car-Rentals-In-Winchester.d6046207.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.com/Winchester.d6046207.Destination-Travel-Guides) # Winchester, IN ## Travel Guide ## Visit Winchester Things to do - Winchester Hotel Deals - Vacation Rentals in Winchester ![Randolph Inn and Suites](https://images.trvl-media.com/lodging/2000000/1780000/1778600/1778532/c5613c1c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Randolph Inn and Suites 890 E Washington Winchester IN $108 nightly $121 total Mar 26 - Mar 27 Total with taxes and fees Stay at this hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Winchester Golf Club and Winchester Speedway are located ... 9/10 Wonderful! (252 reviews) It’s was good for the money! Would stay again! Reviewed on Mar 8, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F26%2F2026&endDate=3%2F27%2F2026&selected=1778532&PinnedHotelID=1778532&HadPinnedHotel=true®ionId=6046207) ![Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA](https://images.trvl-media.com/lodging/25000000/24890000/24889100/24889054/f29bf352_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA Winchester IN Book a stay at this family-friendly vacation home in Winchester. Enjoy free WiFi, private pools, and a garden. Popular attractions Winchester Golf Club and Winchester ... 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 Mar 8, 2026 [Get rates](https://expedia.com/Hotel-Search?startDate=4%2F8%2F2026&endDate=4%2F9%2F2026&selected=24889054&PinnedHotelID=24889054&HadPinnedHotel=true®ionId=6046207) [](https://expedia.com/Hotel-Search?startDate=4%2F8%2F2026&endDate=4%2F9%2F2026&selected=24889054&PinnedHotelID=24889054&HadPinnedHotel=true®ionId=6046207) ![Baymont by Wyndham Richmond I-70](https://images.trvl-media.com/lodging/1000000/10000/4400/4345/97f2f944_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Baymont by Wyndham Richmond I-70 912 Mendleson Dr Richmond IN Fully refundableReserve now, pay when you stay $67 nightly $75 total Mar 29 - Mar 30 Total with taxes and 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 ... 8.4/10 Very Good! (1,008 reviews) We had a long drive behind us with more to come so stopped for the night. The hotel wasn’t fancy but was immaculate, comfortable, value-priced, and offered a breakfast spread equal to hotels that are 1-2 tiers more expensive. (Ask for cook-to-order eggs of any style!) Staff were friendly and competent. ... Reviewed on Mar 25, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=4345&PinnedHotelID=4345&HadPinnedHotel=true®ionId=6046207) [See all 136 properties in Winchester](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=3%2F26%2F2026&endDate=3%2F27%2F2026®ionId=6046207) 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](https://images.trvl-media.com/lodging/25000000/24890000/24889100/24889054/f29bf352_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA Winchester IN Book a stay at this family-friendly vacation home in Winchester. Enjoy free WiFi, private pools, and a garden. Popular attractions Winchester Golf Club and Winchester ... 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 Mar 8, 2026 [](https://expedia.com/Winchester-Hotels-Indoor-Pool.h24889054.Hotel-Information) ![Indoor Gymnasium, Seasonal Pool, 7 Bedroom, Sleeps 28](https://images.trvl-media.com/lodging/56000000/55620000/55612100/55612074/82704f5c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Indoor Gymnasium, Seasonal Pool, 7 Bedroom, Sleeps 28 Fort recovery OH 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! (207 reviews) 5th year we have been here as a huge family! Always fun. We love, pickleball, dodgeball, the hot tub, basketball, pool, etc! Reviewed on Mar 8, 2026 [](https://expedia.com/Fort-Recovery-Hotels-Inviting-Family-Retreat-With-Pool.h55612074.Hotel-Information) ![Westcott Mansion with Pickleball Court & Huge Gazebo](https://images.trvl-media.com/lodging/91000000/90260000/90254300/90254204/37035f85_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Westcott Mansion with Pickleball Court & Huge Gazebo Richmond IN Book a stay at this family-friendly vacation home in Richmond. Enjoy a garden, laundry facilities, and tennis courts. Popular attractions Wayne County Historical ... 9.8/10 Exceptional! (35 reviews) We had a wonderful stay at the Westcott Mansion!! The home is so beautiful, clean, and wonderfully historically charming. The space felt welcoming and comfortable throughout, and the amenities made the stay even better!The pickleball court was a fun bonus, and the large gazebo created a perfect spot ... Reviewed on Nov 11, 2025 [](https://expedia.com/Richmond-Hotels-Westcott-Mansion-With-Pickleball-Court-Huge-Gazebo.h90254204.Hotel-Information) [See all properties in Winchester](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=6046207&sort=VACATION_RENTAL) 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. ## Check Winchester hotel availability [Tonight ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6046207&startDate=2026-03-25&endDate=2026-03-26)[Mar 25 - Mar 26](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6046207&startDate=2026-03-25&endDate=2026-03-26) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6046207&startDate=2026-03-26&endDate=2026-03-27)[Mar 26 - Mar 27](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6046207&startDate=2026-03-26&endDate=2026-03-27) [This weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6046207&startDate=3%2F27%2F2026&endDate=3%2F29%2F2026)[Mar 27 - Mar 29](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6046207&startDate=3%2F27%2F2026&endDate=3%2F29%2F2026) [Next weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6046207&startDate=4%2F3%2F2026&endDate=4%2F5%2F2026)[Apr 3 - Apr 5](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6046207&startDate=4%2F3%2F2026&endDate=4%2F5%2F2026) ### Popular places to visit #### Winchester Speedway Catch an event at Winchester Speedway during your trip to Winchester. [](https://expedia.com/Winchester-Speedway-Winchester.d6289044.Vacation-Attraction) #### Winchester Golf Club Enjoy a round of golf in Winchester at Winchester Golf Club. [](https://expedia.com/Winchester-Golf-Club-Winchester.d553248621582419855.Vacation-Attraction) #### Randolph County Courthouse After visiting Randolph County Courthouse, make a plan to see the other sights and activities in Winchester. 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