Title: Winchester Holidays 2026 from £1,007 | Expedia.co.uk [Hotels in Winchester](https://expedia.co.uk/Winchester-Hotels.d7876.Travel-Guide-Hotels)[Holiday Rentals in Winchester](https://expedia.co.uk/Winchester-Holiday-Rentals.d7876.Travel-Guide-HolidayRentals)[Winchester Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Winchester.d7876.Car-Hire-Guide) ![](https://images.trvl-media.com/place/6056879/31f89911-167f-41d8-88d6-62f9fb8763d2.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Winchester Holidays from £1,007 ## 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 Take away the hard part of organising your next epic adventure with a Winchester holiday package. Whether you're visiting for its landmarks, food or other highlights, this city offers endless possibilities for fun. Every trip to Winchester needs a well-thought-out itinerary. Fill yours with attractions like [Bluegrass Heritage Museum](https://www.expedia.co.uk/Bluegrass-Heritage-Museum-Lexington.d553248621561880736.Attraction), [Lykins Park](https://www.expedia.co.uk/Lykins-Park-Winchester.d6263146.Attraction) and [Southwind Golf Course](https://www.expedia.co.uk/Southwind-Golf-Course-Lexington.d6263194.Attraction). Your ultimate Winchester holiday is just a few clicks away. Browse hotels, airfares and more on Expedia for an adventure that's tailored to suit your travel style. ## Top Winchester Flight + Hotel Deals Price found within the past 48 hours. Click for updated prices. ![Home2 Suites by Hilton Lexington University / Medical Center](https://images.trvl-media.com/lodging/11000000/10630000/10627700/10627700/19fadf34_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Home2 Suites by Hilton Lexington University / Medical Center Zandale £1,007 per person 2 May - 7 May found 1 day ago Return direct flight included Edinburgh (EDI) to Lexington (LEX) 8.8/10 Excellent! (1,000 reviews) The room was spotless and the person at the front desk was very kind and helpful. Reviewed on 17 Feb 2026 ![The Manchester ](https://images.trvl-media.com/lodging/93000000/92440000/92430600/92430541/f02815a4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Manchester Distillery District £1,591 per person 13 Apr - 19 Apr found 1 day ago Return direct flight included London (LHR) to Lexington (LEX) 9.6/10 Exceptional! (1,046 reviews) Room was spotless and the tile work was amazing. Nice choices for the mini-bar Reviewed on 28 Feb 2026 ![The Campbell House Lexington, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/30000/27100/27029/2fd2c43b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Campbell House Lexington, Curio Collection by Hilton £1,261 per person 13 Apr - 19 Apr found 1 day ago Return direct flight included London (LHR) to Lexington (LEX) 8.2/10 Very Good! (1,000 reviews) The tub would not hold water for a bath. Was truly looking forward a hot soak Reviewed on 28 Feb 2026 ![DoubleTree Suites by Hilton Hotel Lexington](https://images.trvl-media.com/lodging/1000000/10000/9900/9900/f18d8c34_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### DoubleTree Suites by Hilton Hotel Lexington £1,008 per person 2 May - 7 May found 1 day ago Return direct flight included Edinburgh (EDI) to Lexington (LEX) 8.8/10 Excellent! (1,002 reviews) Everything was nice. Reviewed on 23 Feb 2026 ![The Sire Hotel Lexington, Tapestry Collection by Hilton](https://images.trvl-media.com/lodging/27000000/26690000/26680500/26680449/df5ce668_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Sire Hotel Lexington, Tapestry Collection by Hilton Downtown Lexington £1,339 per person 2 May - 7 May found 1 day ago Return direct flight included Edinburgh (EDI) to Lexington (LEX) 9.4/10 Exceptional! (838 reviews) I have stayed there several times. Always enjoyable. Clean and friendly. Reviewed on 4 Feb 2026 ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-uk-fr-de.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Holiday Sale Members save up to 40% on hotels and holiday homes. Plan this year’s big trip and save. [Book now](https://expedia.co.uk/cheap-deals?rfrr=PKG_SPRING_PROMO_7876) ## Winchester Essential Information | Language | English | | --------------- | ----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Closest Airport | Blue Grass Airport (LEX) | | Population | 18,400 | | Max Temp Winter | 4ºC | | Max Temp Summer | 29ºC | | Top Sights | [Bluegrass Heritage Museum](https://www.expedia.co.uk/Bluegrass-Heritage-Museum-Lexington.d553248621561880736.Attraction), [Community Park](https://www.expedia.co.uk/Community-Park-Lexington.d6263168.Attraction) and [Lykins Park](https://www.expedia.co.uk/Lykins-Park-Winchester.d6263146.Attraction) | ## Top hotels in Winchester ![The Manchester ](https://images.trvl-media.com/lodging/93000000/92440000/92430600/92430541/f02815a4_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Manchester 941 Manchester St Lexington KY Fully refundableReserve now, pay when you stay £159 22 Mar - 23 Mar includes taxes & fees 9.6/10 Exceptional! (1,178 reviews) Room was spotless and the tile work was amazing. Nice choices for the mini-bar Reviewed on 28 Feb 2026 [](https://expedia.co.uk/Hotel-Search?startDate=22%2F03%2F2026&endDate=23%2F03%2F2026&selected=92430541&PinnedHotelID=92430541&HadPinnedHotel=true®ionId=7876) ![DoubleTree Suites by Hilton Hotel Lexington](https://images.trvl-media.com/lodging/1000000/10000/9900/9900/f18d8c34_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### DoubleTree Suites by Hilton Hotel Lexington 2601 Richmond Rd Lexington KY Fully refundableReserve now, pay when you stay £100 12 Mar - 13 Mar includes taxes & fees 8.8/10 Excellent! (1,001 reviews) Everything was nice. Reviewed on 23 Feb 2026 [](https://expedia.co.uk/Hotel-Search?startDate=12%2F03%2F2026&endDate=13%2F03%2F2026&selected=9900&PinnedHotelID=9900&HadPinnedHotel=true®ionId=7876) ![Hilton Lexington/Downtown](https://images.trvl-media.com/lodging/1000000/10000/2200/2101/b9ab6063_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Lexington/Downtown 369 West Vine Street Lexington KY Fully refundableReserve now, pay when you stay £130 8 Mar - 9 Mar includes taxes & fees 8.4/10 Very Good! (1,002 reviews) Of the 4 Hilton's I stay in regularly in KY and TN, this one has room for improvement. Building is very old and was the most luxurious of the downtown hotels. Unfortunately all that was lost during a bad renovation. Property is not a luxury hotel at all. Problems everywhere. Horrible wall paper pealing ... Reviewed on 28 Feb 2026 [](https://expedia.co.uk/Hotel-Search?startDate=08%2F03%2F2026&endDate=09%2F03%2F2026&selected=2101&PinnedHotelID=2101&HadPinnedHotel=true®ionId=7876) [See all 1,164 properties in Winchester](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=02%2F03%2F2026&endDate=03%2F03%2F2026®ionId=7876) 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 ![Kentucky Horse Park showing land animals](https://images.trvl-media.com/place/6062603/def85b29-11a4-4658-9dd9-2740c5e40aee.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Kentucky Horse Park Enjoy a trip to Kentucky Horse Park and popular activities such as horse riding in Lexington. Attend a sporting event or simply enjoy the lively bars while you're in the area. [](https://expedia.co.uk/Kentucky-Horse-Park-Lexington.d6062603.Attraction) ![Panorama of an autumn, colorful lawn surrounded by buildings in downtown Lexington, Kentucky](https://images.trvl-media.com/place/6062605/185f7d52-ee3c-4550-bf71-3939a597b217.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### University of Kentucky Take a campus tour or just explore the area of University of Kentucky during your travels in Lexington. Attend a sporting event or simply enjoy the lively bars while you're in the area. [](https://expedia.co.uk/University-Of-Kentucky-Lexington.d6062605.Attraction) ![The bottling line for the special single barrel Blantons Bourbon. ](https://images.trvl-media.com/place/7262/a9276a3e-fd4a-44ad-bf04-3f76dcbda506.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Buffalo Trace Distillery You can take time to visit Buffalo Trace Distillery during your travels to Frankfort. You can seek out the hiking trails while in the area. [](https://expedia.co.uk/Buffalo-Trace-Distillery-Lexington.d553248621587339578.Attraction) ### What to do in Winchester ![Experience Rebecca Ruth Chocolate Tour & Museum!](https://mediaim.expedia.com/localexpert/1358370/fef83701-f93b-4351-8789-3ac82fda4d15.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Experience Rebecca Ruth Chocolate Tour & Museum! £7 per adult **80%** of travellers recommend [](https://expedia.co.uk/things-to-do/experience-rebecca-ruth-chocolate-tour-museum.a1358370.activity-details) ![Unique Horse Farm Tours with Insider Access to Private Farms](https://mediaim.expedia.com/localexpert/674444/83731e47-46fb-498d-8652-e673bdca50fd.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Unique Horse Farm Tours with Insider Access to Private Farms £44 per adult **90%** of travellers recommend [](https://expedia.co.uk/things-to-do/unique-horse-farm-tours-with-insider-access-to-private-farms.a674444.activity-details) ![Experience Rebecca Ruth Chocolate Tour & Museum: Group limit 15](https://mediaim.expedia.com/localexpert/1358355/c1a20b52-8a00-4314-8ceb-e20245e3f0ce.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Experience Rebecca Ruth Chocolate Tour & Museum £7 per adult [](https://expedia.co.uk/things-to-do/experience-rebecca-ruth-chocolate-tour-museum.a1358355.activity-details) [See all activities in Winchester](https://expedia.co.uk/things-to-do/search?rid=7876) ## Explore a world of travel with Expedia - 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[Flights from Manchester (MAN) to Lexington (LEX) ](https://www.expedia.co.uk/lp/flights/man/lex/manchester-to-lexington) - [Flights from Chicago (ORD) to Lexington (LEX) ](https://www.expedia.co.uk/lp/flights/ord/lex/chicago-to-lexington) - [Bowen Holidays ](https://www.expedia.co.uk/Bowen.d3000438356.Holidays-City-Breaks) - [Buckley Wildlife Sanctuary & Audobon Center ](https://www.expedia.co.uk/Buckley-Wildlife-Sanctuary-Audobon-Center-Lexington.d553248621532656273.Attraction) - [Buffalo Trace Distillery ](https://www.expedia.co.uk/Buffalo-Trace-Distillery-Lexington.d553248621587339578.Attraction) - [Visit Clay City ](https://www.expedia.co.uk/Clay-City.dx3000438412) - [Danville Holidays ](https://www.expedia.co.uk/Danville.d6059511.Holidays-City-Breaks) - [Ezel Holidays ](https://www.expedia.co.uk/Ezel.d3000347329.Holidays-City-Breaks) - [Jacobson Park ](https://www.expedia.co.uk/Jacobson-Park-Lexington.d553248621557934641.Attraction) - [Kentucky Horse Park ](https://www.expedia.co.uk/Kentucky-Horse-Park-Lexington.d6062603.Attraction) - [Kentucky Reptile Zoo ](https://www.expedia.co.uk/Kentucky-Reptile-Zoo-Slade.d553248621532657835.Attraction) - [Kentucky State Capitol ](https://www.expedia.co.uk/Kentucky-State-Capitol-Lexington.d6091519.Attraction) - [Kentucky Holidays ](https://www.expedia.co.uk/Kentucky.d219.Holidays-City-Breaks) - [Kroger Field ](https://www.expedia.co.uk/Kroger-Field-Lexington.d6062633.Attraction) - [Lake Linville Park ](https://www.expedia.co.uk/Lake-Linville-Park-Mount-Vernon.d553248621532657811.Attraction) - [Lexington Opera House ](https://www.expedia.co.uk/Lexington-Opera-House-Downtown-Lexington.d6173362.Attraction) - [Lexington Holidays ](https://www.expedia.co.uk/Lexington.d603003.Holidays-City-Breaks) - [Visit Lexington ](https://www.expedia.co.uk/Lexington.dx603003) - [Visit Mount Sterling ](https://www.expedia.co.uk/Mount-Sterling.dx8990) - [Nannine Clay Wallis Arboretum ](https://www.expedia.co.uk/Nannine-Clay-Wallis-Arboretum-Paris.d553248621559866399.Attraction) - [Nicholasville Holidays ](https://www.expedia.co.uk/Nicholasville.d181401.Holidays-City-Breaks) - [Northern Kentucky Holidays ](https://www.expedia.co.uk/Northern-Kentucky.d6059486.Holidays-City-Breaks) - [Orlando Holidays ](https://www.expedia.co.uk/Orlando.d6338686.Holidays-City-Breaks) - [Paint Lick Holidays ](https://www.expedia.co.uk/Paint-Lick.d6348052.Holidays-City-Breaks) - [Paris Holidays ](https://www.expedia.co.uk/Paris.d9076.Holidays-City-Breaks) - [Rebecca Ruth Candy Tours & Museum ](https://www.expedia.co.uk/Rebecca-Ruth-Candy-Tours-Museum-Lexington.d553248621532656326.Attraction) - [Red River Gorge Geological Area ](https://www.expedia.co.uk/Red-River-Gorge-Geological-Area-Kentucky.d654058571148623872.Attraction) - [Shaker Village of Pleasant Hill ](https://www.expedia.co.uk/Shaker-Village-Of-Pleasant-Hill-Harrodsburg.d6248009.Attraction) - [Slade Holidays ](https://www.expedia.co.uk/Slade.d158793.Holidays-City-Breaks) - [Stanford Holidays ](https://www.expedia.co.uk/Stanford.d6193299.Holidays-City-Breaks) - [University of Kentucky ](https://www.expedia.co.uk/University-Of-Kentucky-Lexington.d6062605.Attraction) - [Versailles Holidays ](https://www.expedia.co.uk/Versailles.d7459.Holidays-City-Breaks) - [West Sixth Brewing ](https://www.expedia.co.uk/West-Sixth-Brewing-Northside-District.d553248621587293715.Attraction) - [Woodford Reserve Distillery ](https://www.expedia.co.uk/Woodford-Reserve-Distillery-Frankfort.d6248006.Attraction) - [Zoe Holidays ](https://www.expedia.co.uk/Zoe.d553248635975257913.Holidays-City-Breaks) - [Car hire near Lexington ](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Lexington.d603003.Car-Hire-Guide) - [Car hire Paris ](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Paris.d9076.Car-Hire-Guide) - [Car hire Richmond ](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Richmond.d6148.Car-Hire-Guide) - [Lexington Holiday Rentals ](https://www.expedia.co.uk/Lexington-Holiday-Rentals.d603003.Travel-Guide-HolidayRentals) - [Nicholasville Holiday Rentals ](https://www.expedia.co.uk/Nicholasville-Holiday-Rentals.d181401.Travel-Guide-HolidayRentals) - [Paris Holiday Rentals ](https://www.expedia.co.uk/Paris-Holiday-Rentals.d9076.Travel-Guide-HolidayRentals) - [Things to do in Lexington ](https://www.expedia.co.uk/Things-To-Do-In-Lexington.d603003.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. 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