Title: Book the Best Winchester LUXURY Hotels - Upscale Hotels in Winchester, VA | Expedia.ca [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) # Find luxury hotels in Winchester, VA ![](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 Luxury Hotels Tonight [Oct 16 - Oct 17](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-10-16&endDate=2025-10-17&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 17 - Oct 18](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-10-17&endDate=2025-10-18&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-10-17&endDate=2025-10-19&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-10-24&endDate=2025-10-26&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winchester Luxury Hotels ![Coffee service](https://images.trvl-media.com/lodging/1000000/50000/43100/43087/f87cf676.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/50000/43100/43087/598f2666.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/50000/43100/43087/7faefe8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Laundry room](https://images.trvl-media.com/lodging/1000000/50000/43100/43087/3bfa30f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Motel 6 Winchester, VA Winchester 8.2/10 Very good (1005) "Friendly staff, spotless rooms, safe property and location. Great place for those traveling with pets." CA $95 CA $108 total includes taxes & fees Nov 15 - Nov 16 [](https://www.expedia.ca/Winchester-Hotels-Motel-6-Winchester.h43087.Hotel-Information) ![In-room safe, desk, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/28616e5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/w3000h1997x0y0-2ca33d0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/d7931645.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room, 2 Double Beds, Smoking](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/65ba6c12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Travelodge by Wyndham Winchester Winchester 8.6/10 Excellent (1089) "It's been a great stay so far" CA $97 CA $105 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/40000/34500/34467/299522c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/40000/34500/34467/06bbe3a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Suite, 1 Queen Bed](https://images.trvl-media.com/lodging/1000000/40000/34500/34467/b112d555.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/1000000/40000/34500/34467/d6942b45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wayside Inn Middletown 9.2/10 Wonderful (407) "Clean room and friendly staff. Air conditioning was very noisy and the inn needs some upkeep, but we would stay there again." CA $155 CA $186 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Middletown-Hotels-Wayside-Inn.h34467.Hotel-Information) ![Building design](https://images.trvl-media.com/lodging/4000000/3900000/3893400/3893306/b2ef5cc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/4000000/3900000/3893400/3893306/87742930.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Select Comfort beds, individually decorated, individually furnished](https://images.trvl-media.com/lodging/4000000/3900000/3893400/3893306/6c754bbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/4000000/3900000/3893400/3893306/32a544d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Strasburg Strasburg 7.8/10 Good (731) "The place was closed and looks like it has been for quite sometime. The outside was run down and litter all over. We drove 5 hours to get there and even had a confirmation number from hotel. Com. Very disappointed!!!!!!" [](https://www.expedia.ca/Winchester-Hotels-Hotel-Strasburg.h3893306.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/16000000/15800000/15799900/15799885/39d8617d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, soundproofing, iron/ironing board, cribs/infant beds](https://images.trvl-media.com/lodging/16000000/15800000/15799900/15799885/08468627.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/16000000/15800000/15799900/15799885/030e20be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/16000000/15800000/15799900/15799885/7d6688ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Twi-Lite Inn Front Royal 8.2/10 Very good (526) "Great pool and quiet area to stay in" CA $107 CA $119 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Winchester-Hotels-Twi-Lite-Motel.h15799885.Hotel-Information) ![2 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5a07226c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5707228d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/a8e7d0d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/bff9ad76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The George Washington Hotel, A Wyndham Grand Hotel Old Town Winchester 9.4/10 Exceptional (1015) "Very nice hotel " CA $178 CA $202 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![Desk, blackout drapes, free cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/1000000/30000/24100/24072/9bc5a360.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/24100/24072/ae590780.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/1000000/30000/24100/24072/4ef3053b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Laundry room](https://images.trvl-media.com/lodging/1000000/30000/24100/24072/0e2d3d92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Red Roof Inn Winchester, VA Winchester 7.4/10 Good (1010) "Staff was very respectful and friendly " CA $90 CA $98 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Winchester-Hotels-Red-Roof-Inn-Winchester.h24072.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/17b0fc68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/16920465.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/769f9c2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout drapes, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/a888dfb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Winchester-University/Mall Area Winchester 9.0/10 Wonderful (1019) "Staff was excellent !!! Hotel was clean and comfortable in great location !!! Would stay here again !!! " CA $160 CA $181 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/16600/16597/e0dc7477.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/20000/16600/16597/0ae639c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/16600/16597/7a3981b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/20000/16600/16597/cf3b472b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Clarion Inn & Conference Center Winchester 7.8/10 Good (952) "Great location and staff... spacious and clean will definitely be back " [](https://www.expedia.ca/Winchester-Hotels-Clarion-Inn-Conference-Center.h16597.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/892900/892882/53b7b275.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/892900/892882/502f6bec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/900000/892900/892882/decc147c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/892900/892882/d2967872.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleep Inn & Suites Winchester near University Winchester 7.8/10 Good (1006) "Breakfast was okay " CA $104 CA $113 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Winchester-Hotels-Sleep-Inn-Suites.h892882.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-30&endDate=2025-10-31®ionId=6056879&adults=2&star=50&sort=RECOMMENDED&openPlayBack=true) ## Find out more about Winchester ### Winchesterand its attractions for luxury travelers Winchester, Virginia, offers a blend of history, culture, and natural beauty that will appeal to luxury travellers. Begin your exploration at the Museum of the Shenandoah Valley, where you can admire an impressive collection of American art and historic artefacts, all set against stunning gardens that invite leisurely strolls. Next, delve into Winchester's Civil War heritage at the historic Handley Regional Library, a beautifully restored building that also offers a glimpse into the city’s past. For a taste of the local cuisine, treat yourself to a meal at the renowned 1840s Courthouse Restaurant, where the elegant stay complements a menu crafted from seasonal, locally-sourced ingredients. Outdoor enthusiasts can enjoy the breathtaking views from the nearby Blue Ridge Mountains, perfect for hiking or a scenic drive. Additionally, the vibrant Old Town Winchester is a charming area to explore, filled with boutique shops and art galleries, offering a perfect backdrop for an afternoon of indulgence. For accommodation, consider staying at the luxurious George Washington Hotel, which combines modern amenities with historic elegance, ensuring an unforgettable experience. Here, attentive staff cater to your every need, allowing you to relax and immerse yourself in the rich tapestry of Winchester. ### Find the best luxury hotels and resorts in Winchester For discerning travellers seeking a touch of elegance in Winchester, these luxurious hotels offer a sophisticated retreat with exceptional amenities and services. [The George Washington Hotel, A Wyndham Grand Hotel](https://www.expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) - **Why it's great for a luxury retreat:** The George Washington Hotel stands out as a premier luxury destination for travellers in Winchester, an impressive guest review rating of 9.4. This exquisite hotel offers valet parking and a dedicated concierge service, ensuring a seamless and personalised experience for each guest. The premium bedding guarantees restful nights, while the onsite spa and indoor pool provide the perfect escape for relaxation and rejuvenation. - **Other amenities:** Guests can indulge in a range of additional features, including a 24-hour fitness centre, complimentary internet, and early check-in or late check-out options for added convenience. The hotel showcases its Georgian hotel design, exuding historical charm while accommodating modern luxuries. With daily housekeeping, free toiletries, and in-room massage services, every detail is thoughtfully catered to enhance your stay. For those who enjoy outdoor activities, the hotel is ideally located near skiing, golfing, and hiking opportunities. - **Neighborhood:** Old Town Winchester - **Nearby attractions:** Handley Regional Library - 0.4 km, Bright Box Theater - 0.4 km, Old Court House Civil War Museum - 0.4 km ## Top Winchester Hotel Reviews ![La Quinta Inn & Suites by Wyndham Winchester](//images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb_y.jpg) ### La Quinta Inn & Suites by Wyndham Winchester 10/10 Excellent "Was just one night with group of friends. Location was great, easy check in and out, good breakfast and comfy beds. Would highly recommend. " [](https://expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![Hampton Inn Winchester-University/Mall Area](//images.trvl-media.com/lodging/1000000/20000/20000/19971/17b0fc68_y.jpg) ### Hampton Inn Winchester-University/Mall Area 10/10 Excellent "Great stay! Would definitely would stay again!" [](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.Hotel-Information) ![Travelodge by Wyndham Winchester](//images.trvl-media.com/lodging/1000000/10000/9600/9600/28616e5b_y.jpg) ### Travelodge by Wyndham Winchester 10/10 Excellent "I love this place. Very clean. I've been to many motels in the area and they are horrible, filthy, unkempt properties. Here they have an elevator which is very easy on the legs and arms when getting one's luggage in. Very congenial owner. They don't discriminate against smokers. Other motels in the area put a smoker in rooms that weren't even cleaned. I would recommend this Travel Lodge to all types of guests. Business or leisure." [](https://expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) ![The George Washington Hotel, A Wyndham Grand Hotel](//images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5a07226c_y.jpg) ### The George Washington Hotel, A Wyndham Grand Hotel 10/10 Excellent "Very nice hotel " [](https://expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![Motel 6 Winchester, VA](//images.trvl-media.com/lodging/1000000/50000/43100/43087/f87cf676_y.jpg) ### Motel 6 Winchester, VA 10/10 Excellent "Always da best motel an experience " [](https://expedia.ca/Winchester-Hotels-Motel-6-Winchester.h43087.Hotel-Information) ![Sleep Inn & Suites Winchester near University](//images.trvl-media.com/lodging/1000000/900000/892900/892882/53b7b275_y.jpg) ### Sleep Inn & Suites Winchester near University 10/10 Excellent "Good" [](https://expedia.ca/Winchester-Hotels-Sleep-Inn-Suites.h892882.Hotel-Information) ![Spark by Hilton Winchester](//images.trvl-media.com/lodging/1000000/120000/117800/117743/ac575b89_y.jpg) ### Spark by Hilton Winchester 10/10 Excellent "The staff was very friendly. The room was clean. They supplied enough towels. The breakfast bar had variety. It was quiet for us, but we had a 2 year old that is very boisterous and likes to dance so I don't know if that bothered anyone around us or below us." [](https://expedia.ca/Winchester-Hotels-Spark-By-Hilton-Winchester.h117743.Hotel-Information) ## Frequently asked questions ### Are you looking for a luxury hotel for your Winchester vacation? > Expedia can help you arrange a flight to Martinsburg, WV (MRB-Eastern West Virginia Regional) airport or Washington Dulles Intl. Airport (IAD) airport, and then you can select from various places to stay that will deliver the luxury you'd like to find. Amenities are important when you plan a trip, so we make it easy to get what you want to make your stay relaxing and comfortable. If you want an upscale hotel with fine dining, a spa, or several swimming pools, Expedia can help you find the best luxury hotel experience that Winchester has to offer. During your visit, you might want to enjoy the great views and shopping which Winchester is known for. ### When can I expect good weather in Winchester? > Planning for the weather is a good way to make your trip to Winchester relaxing and enjoyable, especially when you're splurging. The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 36°F. Average annual precipitation for Winchester is 46 inches. ### What's there to see and do in Winchester? > Enjoy all that Winchester has to offer and visit Bright Box Theater, Shenandoah Valley Discovery Museum, and Winchester Little Theater. If you have extra time while you're in the area, you might want to see Patsy Cline Historic House and Museum of the Shenandoah Valley. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - More ways to book - [3 Star Hotels in Old Town Winchester](https://www.expedia.ca/3Star-Old-Town-Winchester-Winchester-Hotels.s30-n6164092-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Stephens City](https://www.expedia.ca/4Star-Stephens-City-Hotels.s40-0-d12076.Travel-Guide-Filter-Hotels) - [Hotels near Apple Blossom Mall](https://www.expedia.ca/Apple-Blossom-Mall-Hotels.0-l6164018-0.Travel-Guide-Filter-Hotels) - [Historic Hotels in Berryville](https://www.expedia.ca/Berryville-Hotels-Historic-Hotel.0-0-d184082-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Berryville](https://www.expedia.ca/Berryville-Hotels-Luxury-Hotel.0-0-d184082-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Berryville Hotels](https://www.expedia.ca/Berryville-Hotels.d184082.Travel-Guide-Hotels) - 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[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) - [Visit Millwood](https://www.expedia.ca/Millwood.dx3000460156) - [Book Luxury Hotels in Winchester on Expedia.com](https://www.expedia.com/Winchester-Hotels-Luxury-Hotel.0-0-d6056879-tLuxuryHotel.Travel-Guide-Filter-Hotels)