Title: 5 Stars Hotels in Winchester, Virginia from CA $180 - Find Cheap Winchester Hotels With 5 Stars | Expedia.ca [Winchester Travel Guide](https://expedia.ca/Winchester.dx6056879)[Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d6056879.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d6056879.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.ca/Cheap-Flights-To-Winchester.d6056879.Travel-Guide-Flights)[Things to do in Winchester](https://expedia.ca/Things-To-Do-In-Winchester.d6056879.Travel-Guide-Activities)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d6056879.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d6056879.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/720fb116634761161ecda43d4ca150e7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 5 Stars Hotels in Winchester, Virginia from CA $180 ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](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 [Oct 12 - Oct 13](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-10-12&endDate=2025-10-13&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-10-13&endDate=2025-10-14&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-10-17&endDate=2025-10-19&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-10-24&endDate=2025-10-26&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) ![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) ![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 (365) "The property is at a close proximity to the downtown area. We were able to walk everywhere. Our room was spacious and immaculate. " CA $735 CA $911 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/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) ![Fireplace](https://images.trvl-media.com/lodging/19000000/18620000/18615900/18615848/1ad8e3d8.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) ![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) ### Celebration Retreat Front Royal [](https://www.expedia.ca/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.ca/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.ca/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 [Get rates](https://expedia.ca/Hotel-Search?startDate=26%2F10%2F2025&endDate=27%2F10%2F2025&selected=27700&PinnedHotelID=27700&HadPinnedHotel=true®ionId=6056879) 8.8/10 Excellent! (1,001 reviews) [](https://expedia.ca/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 CA $160 CA $180 total Oct 19 - Oct 20 includes taxes & fees 8.8/10 Excellent! (1,004 reviews) [](https://expedia.ca/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 CA $545 CA $627 total Oct 26 - Oct 27 includes taxes & fees 9.6/10 Exceptional! (28 reviews) [](https://expedia.ca/Leesburg-Hotels-Hotel-Burg.h114275854.Hotel-Information) Still don't see what you're looking for? [See all properties in Winchester.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=13%2F10%2F2025&endDate=14%2F10%2F2025®ionId=6056879&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=13%2F10%2F2025&endDate=14%2F10%2F2025®ionId=6056879&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=13%2F10%2F2025&endDate=14%2F10%2F2025®ionId=6056879&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=13%2F10%2F2025&endDate=14%2F10%2F2025®ionId=6056879&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=13%2F10%2F2025&endDate=14%2F10%2F2025®ionId=6056879&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=13%2F10%2F2025&endDate=14%2F10%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 Come to Winchester and enjoy its history, food, and entertainment. [See all hotels in Winchester](https://www.expedia.ca/Hotel-Search?startDate=2025-10-26&endDate=2025-10-27&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 ## Five Star Hotels in Winchester There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Winchester so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Winchester and get ready to be pampered like never before. #### Get a Great Deal on 5-Star Hotels in Winchester Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places. Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town. #### Make Your Escape to Winchester The results are in, and Winchester 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Winchester! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Winchester today and settle down in the lap of luxury tomorrow. ## Frequently asked questions ### How much does it cost to stay in a 5-star hotel in Winchester? > The amount you pay for a 5-star hotel in Winchester can vary based on the time of year you travel and how long you plan to be away, among a range of factors. Use our price per night filter and other search tools to find the best deal on a luxurious getaway. > > > > - Search for the lowest price per night from CA $180 ### What makes a hotel 5 stars in Winchester? > Flawless guest service is at the heart of every 5-star hotel in Winchester. From the second you arrive, staff ensure your every need is met, whether arranging valet parking or providing a nightly turn-down service. On top of that, hotels must offer top-rate amenities to be eligible for a 5-star rating. These can include luxury bathrooms, spa facilities, pools, gourmet kitchens and knowledgeable concierge. ### Are there any 5-star all-inclusive resorts in Winchester? > Find an upscale escape that includes your lodging, meals, bar and entertainment in Winchester with our filter tool. Search for resorts rated 5 stars and click on the "All inclusive" filter. Make sure you check what's included in the upfront price. 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[Hotels with Bar in Winchester Historic District](https://www.expedia.ca/Winchester-Historic-District-Winchester-Hotels-Hotels-With-Bar.0-n918789051029594112-0-tHotelswithBar.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Winchester Historic District](https://www.expedia.ca/Winchester-Historic-District-Winchester-Hotels-Pet-Friendly-Hotel.0-n918789051029594112-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Winchester Historic District](https://www.expedia.ca/Winchester-Historic-District-Winchester-Hotels-Spa-Hotel.0-n918789051029594112-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Hotels near Winchester Medical Center](https://www.expedia.ca/Winchester-Medical-Center-Hotels.0-l6164057-0.Travel-Guide-Filter-Hotels) - [Flights to Boyce](https://www.expedia.ca/Cheap-Flights-To-Boyce.d184084.Travel-Guide-Flights) - [Flights from Winchester Regional](https://www.expedia.ca/lp/airports/wgo/flights-from-winchester-regional-airport) - [Flights from Clear Brook](https://www.expedia.ca/lp/flights/553248635975870250/flights-from-clear-brook) - [Flights from Blacksburg (BCB) to Winchester (WGO)](https://www.expedia.ca/lp/flights/bcb/wgo/blacksburg-to-winchester) - [Flights from Hartford (BDL) to Winchester (WGO)](https://www.expedia.ca/lp/flights/bdl/wgo/hartford-to-winchester) - [Flights from Baltimore (BWI) to Winchester (WGO)](https://www.expedia.ca/lp/flights/bwi/wgo/baltimore-to-winchester) - [Flights from Denver (DEN) to Winchester (WGO)](https://www.expedia.ca/lp/flights/den/wgo/denver-to-winchester) - [Flights from Dallas (DFW) to Winchester (WGO)](https://www.expedia.ca/lp/flights/dfw/wgo/dallas-to-winchester) - [Flights from El Paso (ELP) to Winchester (WGO)](https://www.expedia.ca/lp/flights/elp/wgo/el-paso-to-winchester) - [Flights from Fort Lauderdale (FLL) to Winchester (WGO)](https://www.expedia.ca/lp/flights/fll/wgo/fort-lauderdale-to-winchester) - [Flights from Greenville (GSP) to Winchester (WGO)](https://www.expedia.ca/lp/flights/gsp/wgo/greenville-to-winchester) - [Flights from Jacksonville (JAX) to Winchester (WGO)](https://www.expedia.ca/lp/flights/jax/wgo/jacksonville-to-winchester) - [Flights from Melbourne (MEL) to Winchester (WGO)](https://www.expedia.ca/lp/flights/mel/wgo/melbourne-to-winchester) - [Flights from Sarasota (SRQ) to Winchester (WGO)](https://www.expedia.ca/lp/flights/srq/wgo/sarasota-to-winchester) - [Flights from Syracuse (SYR) to Winchester (WGO)](https://www.expedia.ca/lp/flights/syr/wgo/syracuse-to-winchester) - [Flights from Calgary (YYC) to Winchester (WGO)](https://www.expedia.ca/lp/flights/yyc/wgo/calgary-to-winchester) - [Flights from Toronto (YYZ) to Winchester (WGO)](https://www.expedia.ca/lp/flights/yyz/wgo/toronto-to-winchester) - [Appleland Sports Center](https://www.expedia.ca/Appleland-Sports-Center-Stephens-City.d553248621587477489.Vacation-Attraction) - [Jim Barnett Park](https://www.expedia.ca/Jim-Barnett-Park-Winchester.d6164028.Vacation-Attraction) - [Book 5 Star Hotels in Winchester on Expedia.com](https://www.expedia.com/5Star-Winchester-Hotels.s50-0-d6056879.Travel-Guide-Filter-Hotels)