Title: The 10 Best 5 Star Hotels in Winchester - 2025 Updated Prices | Expedia.co.uk [Winchester Travel Guide](https://expedia.co.uk/Winchester.dx6056879)[Hotels in Winchester](https://expedia.co.uk/Winchester-Hotels.d6056879.Travel-Guide-Hotels)[Holiday Rentals in Winchester](https://expedia.co.uk/Winchester-Holiday-Rentals.d6056879.Travel-Guide-HolidayRentals)[Flights to Winchester](https://expedia.co.uk/Cheap-Flights-To-Winchester.d6056879.Travel-Guide-Flights)[Things to do in Winchester](https://expedia.co.uk/Things-To-Do-In-Winchester.d6056879.Travel-Guide-Activities)[Winchester Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Winchester.d6056879.Car-Hire-Guide)[Winchester Holidays](https://expedia.co.uk/Winchester.d6056879.Holidays-City-Breaks) ![](https://mediaim.expedia.com/destination/1/720fb116634761161ecda43d4ca150e7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Compare and book 5 Star hotels in Winchester, Virginia ![price find illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Winchester 5 Star Hotels Tonight [15 Sept - 16 Sept](https://www.expedia.co.uk/Hotel-Search?regionId=6056879&startDate=2025-09-15&endDate=2025-09-16&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [16 Sept - 17 Sept](https://www.expedia.co.uk/Hotel-Search?regionId=6056879&startDate=2025-09-16&endDate=2025-09-17&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [19 Sept - 21 Sept](https://www.expedia.co.uk/Hotel-Search?regionId=6056879&startDate=2025-09-19&endDate=2025-09-21&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [26 Sept - 28 Sept](https://www.expedia.co.uk/Hotel-Search?regionId=6056879&startDate=2025-09-26&endDate=2025-09-28&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winchester 5 Star Hotels ![Exterior](https://images.trvl-media.com/lodging/7000000/6030000/6022300/6022232/21ca3455.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/7000000/6030000/6022300/6022232/8a0b17e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Couples treatment room(s), sauna, hot tub, steam room](https://images.trvl-media.com/lodging/7000000/6030000/6022300/6022232/43873b99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/7000000/6030000/6022300/6022232/e6b54e5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Salamander Resort And Spa Middleburg 9.2/10 Wonderful (364) "Property in mint condition " £522 includes taxes & fees 5 Oct - 6 Oct [](https://www.expedia.co.uk/Middleburg-Hotels-Salamander-Resort-And-Spa.h6022232.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/19000000/18620000/18615900/18615848/76ff6888.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/18620000/18615900/18615848/23756abd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/18620000/18615900/18615848/90d74caa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic Area](https://images.trvl-media.com/lodging/19000000/18620000/18615900/18615848/4c3da288.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Celebration Retreat Front Royal [](https://www.expedia.co.uk/Winchester-Hotels-Celebration-Retreat.h18615848.Hotel-Information) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Winchester-Hotels.s50-0-d6056879.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Winchester-Hotels.s50-0-d6056879.Travel-Guide-Filter-Hotels) ## Explore similar 4-star hotels Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Winchester. ![Lansdowne Resort and Spa](https://images.trvl-media.com/lodging/1000000/30000/27700/27700/5ae32850_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Lansdowne Resort and Spa 44050 Woodridge Pkwy, Leesburg, VA £210 17 Sept - 18 Sept includes taxes & fees 8.6/10 Excellent! (1,000 reviews) [](https://expedia.co.uk/Leesburg-Hotels-Lansdowne-Resort-And-Spa.h27700.Hotel-Information) ![DoubleTree by Hilton Front Royal Blue Ridge Shadows](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/204cbf3a_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### DoubleTree by Hilton Front Royal Blue Ridge Shadows 111 Hospitality Drive, Front Royal, VA £85 21 Sept - 22 Sept includes taxes & fees 8.8/10 Excellent! (1,000 reviews) [](https://expedia.co.uk/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.Hotel-Information) ![Hotel Burg](https://images.trvl-media.com/lodging/115000000/114280000/114275900/114275854/2337af83_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hotel Burg 208 S King Street, Leesburg, VA £216 23 Sept - 24 Sept includes taxes & fees 9.6/10 Exceptional! (18 reviews) [](https://expedia.co.uk/Leesburg-Hotels-Hotel-Burg.h114275854.Hotel-Information) Still don't see what you're looking for? [See all properties in Winchester.](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=17%2F09%2F2025&endDate=18%2F09%2F2025®ionId=6056879&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=17%2F09%2F2025&endDate=18%2F09%2F2025®ionId=6056879&star=50&star=50&amenities=POOL)[Spa](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=17%2F09%2F2025&endDate=18%2F09%2F2025®ionId=6056879&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=17%2F09%2F2025&endDate=18%2F09%2F2025®ionId=6056879&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=17%2F09%2F2025&endDate=18%2F09%2F2025®ionId=6056879&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=17%2F09%2F2025&endDate=18%2F09%2F2025®ionId=6056879&star=50&star=50&amenities=WATER_PARK) 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. ## Winchester and related destinations - Winchester - Pueblo - Staunton - Florence - Nyack Stroll through the charming pedestrian mall in the historic district, where shops and excellent restaurants await. Delve into local culture at the Museum of the Shenandoah Valley or catch a show at the Bright Box Theatre. [See all hotels in Winchester](https://www.expedia.co.uk/Hotel-Search?startDate=2025-09-30&endDate=2025-10-01&adults=2®ionId=6056879) ![](https://mediaim.expedia.com/destination/1/720fb116634761161ecda43d4ca150e7.jpg?impolicy=fcrop&w=900&h=566&p=1&q=high) ## Top Winchester Hotel Reviews ## Find out more about Winchester ## Explore a world of travel with Expedia - Explore a world of travel with Expedia ### Hotels in Winchester by Star Rating - [4 Star Hotels in Winchester](https://expedia.co.uk/4Star-Winchester-Hotels.s40-0-d6056879.Travel-Guide-Filter-Hotels) ### Areas of Winchester - [Old Town Winchester Hotels](https://expedia.co.uk/Old-Town-Winchester-Winchester-Hotels.0-n6164092-0.Travel-Guide-Filter-Hotels) ### Accommodation near Winchester attractions - [Hotels near Winchester Little Theater](https://expedia.co.uk/Winchester-Little-Theater-Hotels.0-l6164047-0.Travel-Guide-Filter-Hotels) ### Choose Your Winchester Hotel Style - [Beach Resorts & Hotels in Winchester](https://expedia.co.uk/Winchester-Hotels-Beach-Hotels.0-0-d6056879-tBeachHotels.Travel-Guide-Filter-Hotels) - 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[Winery Hotels in Winchester](https://expedia.co.uk/Winchester-Hotels-Winery-Hotels.0-0-d6056879-tWineryHotels.Travel-Guide-Filter-Hotels) ### More accommodation types in Winchester - [Cabin Rentals in Winchester](https://expedia.co.uk/Winchester-Cabins.d6056879-aaCabins.Travel-Guide-Accommodation) - [B&B in Winchester](https://expedia.co.uk/Winchester-Bed-And-Breakfasts.d6056879-aaBedAndBreakfasts.Travel-Guide-Accommodation) - [Villas in Winchester](https://expedia.co.uk/Winchester-Villas.d6056879-aaVillas.Travel-Guide-Accommodation) ### Recommended cities for you - [Hotels in Las Vegas](https://expedia.co.uk/Las-Vegas-Hotels.d178276.Travel-Guide-Hotels) - [Hotels in New York](https://expedia.co.uk/New-York-Hotels.d178293.Travel-Guide-Hotels) - [Hotels in Orlando](https://expedia.co.uk/Orlando-Hotels.d178294.Travel-Guide-Hotels) - [Hotels in Los Angeles](https://expedia.co.uk/Los-Angeles-Hotels.d178280.Travel-Guide-Hotels) - [Hotels in Miami](https://expedia.co.uk/Miami-Hotels.d178286.Travel-Guide-Hotels) - 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[Hilton Garden Inn Winchester](https://expedia.co.uk/Winchester-Hotels-Hilton-Garden-Inn-Winchester.h2169428.Hotel-Information) - [Skyland](https://expedia.co.uk/Luray-Hotels-Skyland.h421517.Hotel-Information) - [Lansdowne Resort and Spa](https://expedia.co.uk/Leesburg-Hotels-Lansdowne-Resort-And-Spa.h27700.Hotel-Information) - [Salamander Resort And Spa](https://expedia.co.uk/Middleburg-Hotels-Salamander-Resort-And-Spa.h6022232.Hotel-Information) - [Mimslyn Inn Historic Hotels Of America](https://expedia.co.uk/Luray-Hotels-Mimslyn-Inn-Historic-Hotels-Of-America.h9760491.Hotel-Information) - [Hampton Inn Martinsburg](https://expedia.co.uk/Martinsburg-Hotels-Hampton-Inn-Martinsburg.h63064.Hotel-Information) - [Best Western Leesburg Hotel & Conference Center](https://expedia.co.uk/Leesburg-Hotels-Best-Western-Leesburg-Hotel-Conference-Center.h12669.Hotel-Information) [See a list of all hotels in Winchester](https://expedia.co.uk/All-Winchester-Hotels.d6056879.Travel-Guide-City-All-Hotels) ### More ways to book - [Book 5 Star Hotels in Winchester on Expedia.com](https://www.expedia.com/5Star-Winchester-Hotels.s50-0-d6056879.Travel-Guide-Filter-Hotels) ## Frequently asked questions ### How much does it cost to stay in a 5-star hotel in Winchester? > You'll find a variety of pricing options for 5-star hotels in Winchester on Expedia. The amount you pay will depend on when you travel, trip length and other factors. Compare all of the available properties for your chosen dates and make use of our pricing and other filters to score the ideal upscale stay. > > > > - Search for the lowest price per night from £85 ### What makes a hotel 5 stars in Winchester? > In Winchester, a hotel needs to offer a certain number of upscale features to be rated 5 stars. These can include gourmet restaurants, on-site gyms, saunas and spas, luxury toiletries, premium bedding and more. What also sets 5-star hotels apart is their guest-focused service. You can look forward to things like concierge services, nightly turn-down services and in-room massage. Some may even offer special touches such as welcome gifts. ### Are there any 5-star all-inclusive resorts in Winchester? > Our filter tool is the easiest way to narrow down what you're looking for. Check the "All inclusive" and "5-star" boxes to see the most upscale resorts in Winchester where your room, meals, entertainment and activities are included in the upfront price. At these stays, your trip is pure indulgence from the moment you arrive. ![](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 ![QR code to download the app](https://a.travel-assets.com/mad-service/qr-code/footer_qr/3_QR_FOOTER.png)