Title: TOP Luxury Hotels in Winchester, VA for 2026 - Winchester Upscale Hotels | Expedia.co.uk [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)[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://images.trvl-media.com/place/6056879/5a1e10ca-c30d-4d41-816e-f5af84673df6.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__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 Luxury Hotels Tonight [11 Jan - 12 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=6056879&startDate=2026-01-11&endDate=2026-01-12&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [12 Jan - 13 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=6056879&startDate=2026-01-12&endDate=2026-01-13&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [16 Jan - 18 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=6056879&startDate=2026-01-16&endDate=2026-01-18&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) In two weeks [23 Jan - 25 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=6056879&startDate=2026-01-23&endDate=2026-01-25&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Our top choices for 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/d6535fe8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Laundry room](https://images.trvl-media.com/lodging/1000000/50000/43100/43087/7d3e25f0.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 [](https://www.expedia.co.uk/Winchester-Hotels-Motel-6-Winchester.h43087.Hotel-Information) Winchester 8.2/10 Very good (1,002 reviews) "It was clean and in a safe area " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daryl £50 includes taxes & fees 31 Jan - 1 Feb [](https://www.expedia.co.uk/Winchester-Hotels-Motel-6-Winchester.h43087.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/19e0634f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/9d44a9b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Smoking | In-room safe, desk, iron/ironing board, free cots/infant beds](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/e1711cc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Smoking | Living area | LED TV](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/bf0bfb1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Travelodge by Wyndham Winchester [](https://www.expedia.co.uk/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) Winchester 8.6/10 Excellent (1,087 reviews) "Hotels well Located off 81 for a nice pull Off and overnight stay. Staff is friendly and helpful and rooms comfortable and quiet. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stefanie £55 includes taxes & fees 13 Jan - 14 Jan [](https://www.expedia.co.uk/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/1000000/40000/34500/34467/a3d72fc4.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) ![Point of interest](https://images.trvl-media.com/lodging/1000000/40000/34500/34467/9e80fe83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/40000/34500/34467/2f175422.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wayside Inn [](https://www.expedia.co.uk/Middletown-Hotels-Wayside-Inn.h34467.Hotel-Information) Middletown 9.2/10 Wonderful (419 reviews) "Historic inn. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller £67 includes taxes & fees 13 Jan - 14 Jan [](https://www.expedia.co.uk/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) ![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/4000000/3900000/3893400/3893306/6764c676.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) ![Interior detail](https://images.trvl-media.com/lodging/4000000/3900000/3893400/3893306/7482c066.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Strasburg [](https://www.expedia.co.uk/Winchester-Hotels-Hotel-Strasburg.h3893306.Hotel-Information) Strasburg 7.8/10 Good (731 reviews) "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!!!!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Merry [](https://www.expedia.co.uk/Winchester-Hotels-Hotel-Strasburg.h3893306.Hotel-Information) ![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) ![Desk, soundproofing, iron/ironing board, cots/infant beds](https://images.trvl-media.com/lodging/16000000/15800000/15799900/15799885/8303a152.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/16000000/15800000/15799900/15799885/39d8617d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Twi-Lite Inn [](https://www.expedia.co.uk/Winchester-Hotels-Twi-Lite-Motel.h15799885.Hotel-Information) Front Royal 8.2/10 Very good (544 reviews) "Clean, comfortable room. Staff was nice and I really enjoyed my stay. Motel was in a high traffic area, but still a quiet stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel £56 includes taxes & fees 13 Jan - 14 Jan [](https://www.expedia.co.uk/Winchester-Hotels-Twi-Lite-Motel.h15799885.Hotel-Information) ![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) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/50dde1f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/31f87045.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The George Washington Hotel, A Wyndham Grand Hotel [](https://www.expedia.co.uk/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) Old Town Winchester 9.4/10 Exceptional (1,006 reviews) "Great hotel!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) CHARLES £107 includes taxes & fees 18 Jan - 19 Jan [](https://www.expedia.co.uk/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![Desk, blackout curtains, free cots/infant beds, free WiFi](https://images.trvl-media.com/lodging/1000000/30000/24100/24072/9e309977.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/1000000/30000/24100/24072/7b28bc9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/24100/24072/3558059b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Red Roof Inn Winchester, VA [](https://www.expedia.co.uk/Winchester-Hotels-Red-Roof-Inn-Winchester.h24072.Hotel-Information) Winchester 7.4/10 Good (1,003 reviews) "Clean, pet friendly and great check in." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anita Willsie £51 includes taxes & fees 1 Feb - 2 Feb [](https://www.expedia.co.uk/Winchester-Hotels-Red-Roof-Inn-Winchester.h24072.Hotel-Information) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/c10d527c.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) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/800932de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Non Smoking | Desk, blackout curtains, iron/ironing board, free cots/infant beds](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/9346d5ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Winchester-University/Mall Area [](https://www.expedia.co.uk/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.Hotel-Information) Winchester 9.0/10 Wonderful (1,000 reviews) "Great stay! Would definitely would stay again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James £86 includes taxes & fees 18 Jan - 19 Jan [](https://www.expedia.co.uk/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/16600/16597/392e03ee.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/ee7efc02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/16600/16597/927407bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/16600/16597/815bfd26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Clarion Inn & Conference Center [](https://www.expedia.co.uk/Winchester-Hotels-Clarion-Inn-Conference-Center.h16597.Hotel-Information) Winchester 7.8/10 Good (952 reviews) "Great location and staff... spacious and clean will definitely be back " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller [](https://www.expedia.co.uk/Winchester-Hotels-Clarion-Inn-Conference-Center.h16597.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/900000/892900/892882/554af346.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) ![Suite, 1 King Bed with Sofa bed, Non Smoking | Hypo-allergenic bedding, down duvets, desk, iron/ironing board](https://images.trvl-media.com/lodging/1000000/900000/892900/892882/8f2087d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/900000/892900/892882/3c1fc37a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleep Inn & Suites Winchester near University [](https://www.expedia.co.uk/Winchester-Hotels-Sleep-Inn-Suites.h892882.Hotel-Information) Winchester 7.8/10 Good (1,008 reviews) "great stay with breakfast too" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James £61 includes taxes & fees 18 Jan - 19 Jan [](https://www.expedia.co.uk/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.co.uk/Hotel-Search?startDate=2026-01-26&endDate=2026-01-27®ionId=6056879&adults=2&star=50&sort=RECOMMENDED&openPlayBack=true) ## Find out more about Winchester ### Winchesterand its attractions for luxury travelers For luxury travellers seeking an enriching experience in Winchester, Virginia, the historic charm of the town is complemented by several exquisite attractions. Begin your exploration at the picturesque Old Town, where cobblestone streets are lined with boutique shops and gourmet restaurants, perfect for indulging in fine dining or unique shopping. The Museum of the Shenandoah Valley offers a stunning blend of art and history, with beautiful gardens and engaging exhibits that provide a glimpse into the region's rich past. For those who enjoy the great outdoors, the serene beauty of the nearby Shenandoah National Park invites leisurely hikes and breathtaking views, enhancing your stay with nature's splendour. A visit to the Apple Blossom Mall offers a touch of retail therapy, featuring high-end brands and designer stores that cater to discerning shoppers. After a day of exploration, unwind in one of Winchester's luxury hotels, such as the George Washington Hotel, which boasts elegant rooms, a full-service spa, and fine dining options, ensuring a pampered experience. Staying in the heart of Old Town not only allows you to easily access these attractions but also provides a vibrant atmosphere that captures the essence of Winchester, making your visit both memorable and luxurious. ### Find the best luxury hotels and resorts in Winchester For travelers seeking a touch of elegance in Winchester, these hotels offer a perfect blend of luxury and comfort, ensuring an unforgettable stay. [**The George Washington Hotel, A Wyndham Grand Hotel**](https://www.expedia.co.uk/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) - **Why it's great for a luxury retreat:** The George Washington Hotel stands as a beacon of luxury in Old Town Winchester, with an impressive guest review rating of 9.4\. This exquisite hotel features premium bedding for a restful night's sleep and offers valet parking for added convenience. Guests can indulge in the onsite spa, which provides a full range of treatments, ensuring complete relaxation during their stay. - **Other amenities:** The hotel boasts a stunning Georgian design that adds to its charm and elegance. Guests can enjoy an indoor pool, a well-equipped fitness centre available 24 hours, and the option for contactless check-in for a seamless arrival experience. Daily housekeeping keeps the rooms pristine, while the option for late check-out allows for a leisurely departure. Additionally, the hotel's nearby golf, hiking, and skiing ensures that adventurers can easily explore the beautiful surroundings. - **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](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb_y.jpg) ### La Quinta Inn & Suites by Wyndham Winchester 10/10 Excellent "Staff was absolutely wonderful. Hotel was verybeasy to work with the entire time. I would recommend this place." [](https://expedia.co.uk/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![Travelodge by Wyndham Winchester](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/9d44a9b1_y.jpg) ### Travelodge by Wyndham Winchester 10/10 Excellent "Basic accomodations but OK for the price. Everything worked fine andd hotel easy to get to from I-81\. " [](https://expedia.co.uk/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) ![Hampton Inn Winchester-University/Mall Area](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/17b0fc68_y.jpg) ### Hampton Inn Winchester-University/Mall Area 10/10 Excellent "Great breakfast. 24 hr coffee. Clean rooms. Pet friendly! Friendly front desk staff" [](https://expedia.co.uk/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.Hotel-Information) ![The George Washington Hotel, A Wyndham Grand Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5a07226c_y.jpg) ### The George Washington Hotel, A Wyndham Grand Hotel 10/10 Excellent "Staff was amazing! Benjamin and Carla are two of the kindest people ever! " [](https://expedia.co.uk/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ## Frequently asked questions ### Which area of Winchester is best to stay in for luxury hotels? > This area is the heart of Winchester, known for its pedestrian-only walking mall, which is a key feature. Here, you'll find beautifully preserved 18th and 19th-century architecture, independent shops, and a wide array of restaurants and cafes. The district is very walkable, making it easy to stroll between attractions like the Handley Regional Library and the Old Court House Civil War Museum. > > > For couples seeking a refined and convenient stay, Historic Old Town is an excellent choice. The location provides easy access to romantic dinners, leisurely walks, and the chance to explore local history and culture without needing a car. ### How much does a luxury hotel in Winchester cost? ### How can I save on a luxury hotel in Winchester with Expedia? ### Is it cheaper to book a luxury Winchester hotel and flights as a package? ### Can I cancel my luxury hotel reservation on Expedia? ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Holiday Homes - Other - More ways to book - [Berryville Hotels ](https://www.expedia.co.uk/Berryville-Hotels.d184082.Travel-Guide-Hotels) - [Bluemont Hotels ](https://www.expedia.co.uk/Bluemont-Hotels.d6348602.Travel-Guide-Hotels) - [Hilton Hotels in Boyce ](https://www.expedia.co.uk/Boyce-Hotels-Hilton-Hotels.0-0-d184084--bHiltonHotels.Travel-Guide-Filter-Hotels) - [Boyce Hotels ](https://www.expedia.co.uk/Boyce-Hotels.d184084.Travel-Guide-Hotels) - [Hotels with Hot Tubs in Chantilly ](https://www.expedia.co.uk/Chantilly-Hotels-Hotels-With-Hot-Tubs.0-0-d8638-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels) - 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