Title: Winchester Holidays 2026 | Expedia.co.uk [Hotels in Winchester](https://expedia.co.uk/Winchester-Hotels.d12104.Travel-Guide-Hotels)[Holiday Rentals in Winchester](https://expedia.co.uk/Winchester-Holiday-Rentals.d12104.Travel-Guide-HolidayRentals)[Winchester Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Winchester.d12104.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 ## 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 When a city adventure is calling your name, answer it with a Winchester holiday package. With all your travel plans worked out before you leave, all you have to do here is focus on having fun. Any trip to Winchester needs a well-designed itinerary. Fill yours with big-name attractions like [Melrose Vineyards](https://www.expedia.co.uk/Melrose-Vineyards-Roseburg.d6090409.Attraction), [Stewart Park](https://www.expedia.co.uk/Stewart-Park-Roseburg.d553248621561869686.Attraction) and [Winchester Dam](https://www.expedia.co.uk/Winchester-Dam-Roseburg.d6296129.Attraction). Stop daydreaming and start doing. Browse the wide range of options on Expedia today and put your Winchester holiday plans in motion! ## Winchester Essential Information | Language | English | | --------------- | ---------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Max Temp Winter | 10ºC | | Max Temp Summer | 27ºC | | Top Sights | [Wildlife Safari](https://www.expedia.co.uk/Wildlife-Safari-Winston.d6090413.Attraction), [Melrose Vineyards](https://www.expedia.co.uk/Melrose-Vineyards-Roseburg.d6090409.Attraction) and [Reustle Prayer Rock Vineyards](https://www.expedia.co.uk/Reustle-Prayer-Rock-Vineyards-Roseburg.d553248621532642250.Attraction) | ## Top hotels in Winchester ![Singing Waters at N. Umpqua](https://images.trvl-media.com/lodging/94000000/93410000/93403100/93403065/ab4dd7f2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Singing Waters at N. Umpqua Roseburg North OR 10/10 Exceptional! (9 reviews) The pictures are exactly how you will find this home. The remodel is first class, the river view amazing. A native of Roseburg, our family stayed here while visiting family. Very peaceful..hosts were very responsive. Reviewed on 12 Sept 2025 [Get rates](https://expedia.co.uk/Hotel-Search?startDate=05%2F02%2F2026&endDate=06%2F02%2F2026&selected=93403065&PinnedHotelID=93403065&HadPinnedHotel=true®ionId=12104) [](https://expedia.co.uk/Hotel-Search?startDate=05%2F02%2F2026&endDate=06%2F02%2F2026&selected=93403065&PinnedHotelID=93403065&HadPinnedHotel=true®ionId=12104) ![SureStay by Best Western Roseburg](https://images.trvl-media.com/lodging/1000000/540000/539600/539504/abf320fc_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### SureStay by Best Western Roseburg 2855 NW Edenbower Blvd Roseburg OR Fully refundableReserve now, pay when you stay £64 1 Feb - 2 Feb includes taxes & fees 8/10 Very Good! (1,001 reviews) Very comfortable thank you Reviewed on 15 Jan 2026 [](https://expedia.co.uk/Hotel-Search?startDate=01%2F02%2F2026&endDate=02%2F02%2F2026&selected=539504&PinnedHotelID=539504&HadPinnedHotel=true®ionId=12104) ![Riverfront Inn Roseburg](https://images.trvl-media.com/lodging/1000000/20000/16100/16066/81d2a043_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Riverfront Inn Roseburg 315 W Harvard Ave Roseburg OR Fully refundableReserve now, pay when you stay 8.4/10 Very Good! (1,424 reviews) Checkin staff was very welcoming and gave great recommendations for dinner. The room could use an update but nothing that kept me from relaxing. The Riverfront Garden was a nice little walk Reviewed on 17 Jan 2026 [Get rates](https://expedia.co.uk/Hotel-Search?startDate=05%2F02%2F2026&endDate=06%2F02%2F2026&selected=16066&PinnedHotelID=16066&HadPinnedHotel=true®ionId=12104) [](https://expedia.co.uk/Hotel-Search?startDate=05%2F02%2F2026&endDate=06%2F02%2F2026&selected=16066&PinnedHotelID=16066&HadPinnedHotel=true®ionId=12104) [See all 115 properties in Winchester](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=23%2F01%2F2026&endDate=24%2F01%2F2026®ionId=12104) 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) ## 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