Title: Winchester Holidays 2026 from £1,124 | Expedia.co.uk [Hotels in Winchester](https://expedia.co.uk/Winchester-Hotels.d6046207.Travel-Guide-Hotels)[Holiday Rentals in Winchester](https://expedia.co.uk/Winchester-Holiday-Rentals.d6046207.Travel-Guide-HolidayRentals)[Winchester Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Winchester.d6046207.Car-Hire-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Winchester Holidays from £1,124 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to £335 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Packages with flights are ATOL protected #### Your Winchester Holiday History, cuisine, art and more … There's so much to experience with a Winchester holiday package. And with the ability to customise your city getaway, you know it'll be one that's tough to forget. Want to explore? [Winchester Speedway](https://www.expedia.co.uk/Winchester-Speedway-Winchester.d6289044.Attraction), [Winchester Golf Club](https://www.expedia.co.uk/Winchester-Golf-Club-Winchester.d553248621582419855.Attraction) and [Historic Shopping & Dining District of Winchester, Indiana](https://www.expedia.co.uk/Historic-Shopping-Dining-District-Of-Winchester-Winchester.d553248621532658844.Attraction) are among the leading places to visit during your trip to Winchester. Expedia has what you need to escape your routine. Tailor your holiday to Winchester to suit your style of travel, whatever that may look like. ## Top Winchester Flight + Hotel Deals Price found within the past 48 hours. Click for updated prices. ![Wingate by Wyndham Indianapolis Airport Plainfield](https://images.trvl-media.com/lodging/1000000/1000000/990100/990067/f89b9b5d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Wingate by Wyndham Indianapolis Airport Plainfield £1,124 per person 7 May - 10 May found 7 hours ago Return direct flight included London (LON) to Indianapolis (IND) 8.2/10 Very Good! (1,004 reviews) The entire staff was right on point friendly, welcoming, and making sure everything was in place. The rooms were as advertised nice and spacious and the bed comfy and the pillows soft. Our cleaning staff was outstanding always going the extra mile making sure we had everything we needed. The entire hotel was clean and in order and it was extremely crowded the entire time I was there. I will definitely stay there again and recommend to family and friends. . Oh and the breakfast was as good as any. Reviewed on 17 Mar 2026 ![Cowboy Bunkhouse hot tub Lake Farm Nature](https://images.trvl-media.com/lodging/121000000/120110000/120102400/120102330/1c1ec524_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cowboy Bunkhouse hot tub Lake Farm Nature £1,889 per person 7 May - 10 May found 7 hours ago Return direct flight included London (LON) to Indianapolis (IND) No reviews ![Treehouse Hot tub on 60 Acre Farm Near Downtown](https://images.trvl-media.com/lodging/121000000/120110000/120102400/120102359/443866d0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Treehouse Hot tub on 60 Acre Farm Near Downtown £1,768 per person 7 May - 10 May found 7 hours ago Return direct flight included London (LON) to Indianapolis (IND) No reviews ## Winchester Essential Information | Language | English | | --------------- | ----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Population | 4,800 | | Max Temp Winter | 2ºC | | Max Temp Summer | 27ºC | | Top Sights | [Winchester Speedway](https://www.expedia.co.uk/Winchester-Speedway-Winchester.d6289044.Attraction), [Winchester Golf Club](https://www.expedia.co.uk/Winchester-Golf-Club-Winchester.d553248621582419855.Attraction) and [Historic Shopping & Dining District of Winchester, Indiana](https://www.expedia.co.uk/Historic-Shopping-Dining-District-Of-Winchester-Winchester.d553248621532658844.Attraction) | ## Top hotels 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 Fully refundableReserve now, pay when you stay £81 27 Mar - 28 Mar includes taxes & fees 9/10 Wonderful! (252 reviews) It’s was good for the money! Would stay again! Reviewed on 8 Mar 2026 [](https://expedia.co.uk/Hotel-Search?startDate=27%2F03%2F2026&endDate=28%2F03%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 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 [Get rates](https://expedia.co.uk/Hotel-Search?startDate=09%2F04%2F2026&endDate=10%2F04%2F2026&selected=24889054&PinnedHotelID=24889054&HadPinnedHotel=true®ionId=6046207) [](https://expedia.co.uk/Hotel-Search?startDate=09%2F04%2F2026&endDate=10%2F04%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 £56 29 Mar - 30 Mar includes taxes & fees 8.4/10 Very Good! (1,000 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 25 Mar 2026 [](https://expedia.co.uk/Hotel-Search?startDate=29%2F03%2F2026&endDate=30%2F03%2F2026&selected=4345&PinnedHotelID=4345&HadPinnedHotel=true®ionId=6046207) [See all 135 properties in Winchester](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=27%2F03%2F2026&endDate=28%2F03%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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Holidays [](https://expedia.co.uk/lp/theme-holidays/all-inclusive-holidays?rfrr=editorial.All_Inclusive%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Holidays [](https://expedia.co.uk/lp/theme-holidays/beach-holidays?rfrr=editorial.Beach_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/kid-friendly-holidays?rfrr=editorial.Family_Friendly%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Holidays [](https://expedia.co.uk/lp/theme-holidays/golf-holidays?rfrr=editorial.Golf_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Holidays [](https://expedia.co.uk/lp/theme-holidays/luxury-holidays?rfrr=editorial.Luxury_Holidays.click) ![gay friendly holidays](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ+ Holidays [](https://expedia.co.uk/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ+_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Holidays [](https://expedia.co.uk/lp/theme-holidays/romantic-holidays?rfrr=editorial.Romantic_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Holidays [](https://expedia.co.uk/lp/theme-holidays/ski-holidays?rfrr=editorial.Ski_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/22/hero-image-pet-friendly_copy.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Pet Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/pet-friendly-holidays?rfrr=editorial.Pet_Friendly%20Holidays.click) ![Holiday in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.co.uk/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ### Popular places to visit #### Winchester Speedway Catch an event at Winchester Speedway during your trip to Winchester. [](https://expedia.co.uk/Winchester-Speedway-Winchester.d6289044.Attraction) ## 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. Flight-inclusive packages are ATOL protected. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app