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 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](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) - ![](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 [7 Nov - 8 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=6056879&startDate=2025-11-07&endDate=2025-11-08&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [8 Nov - 9 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=6056879&startDate=2025-11-08&endDate=2025-11-09&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [7 Nov - 9 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=6056879&startDate=2025-11-07&endDate=2025-11-09&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [14 Nov - 16 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=6056879&startDate=2025-11-14&endDate=2025-11-16&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) ![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) ![2 restaurants, breakfast, lunch, dinner served; local cuisine ](https://images.trvl-media.com/lodging/7000000/6030000/6022300/6022232/b8f43b35.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) ### Salamander Resort And Spa Middleburg 9.2/10 Wonderful (368) "The property is at a close proximity to the downtown area. We were able to walk everywhere. Our room was spacious and immaculate. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cedric £517 includes taxes & fees 20 Nov - 21 Nov [](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/19000000/18620000/18615900/18615848/90d74caa.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) ![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 £182 23 Nov - 24 Nov includes taxes & fees 8.8/10 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 £91 16 Nov - 17 Nov includes taxes & fees 8.8/10 Excellent! (1,002 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 £272 30 Nov - 1 Dec includes taxes & fees 9.6/10 Exceptional! (32 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=08%2F11%2F2025&endDate=09%2F11%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=08%2F11%2F2025&endDate=09%2F11%2F2025®ionId=6056879&star=50&star=50&amenities=POOL)[Spa](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=08%2F11%2F2025&endDate=09%2F11%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=08%2F11%2F2025&endDate=09%2F11%2F2025®ionId=6056879&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=08%2F11%2F2025&endDate=09%2F11%2F2025®ionId=6056879&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=08%2F11%2F2025&endDate=09%2F11%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=2025-11-21&endDate=2025-11-22&adults=2®ionId=6056879) ![](https://images.trvl-media.com/place/6056879/5a1e10ca-c30d-4d41-816e-f5af84673df6.jpg?impolicy=fcrop&w=900&h=566&p=1&q=high) ## Top Winchester Hotel Reviews ## Find out more about Winchester ## 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 £91 ### 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. ## Explore a world of travel with Expedia - 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)