Title: TOP Luxury Hotels in Winchester, VA for 2025 - 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://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__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 Oct - 12 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=6056879&startDate=2025-10-11&endDate=2025-10-12&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [12 Oct - 13 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=6056879&startDate=2025-10-12&endDate=2025-10-13&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [17 Oct - 19 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=6056879&startDate=2025-10-17&endDate=2025-10-19&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [24 Oct - 26 Oct](https://www.expedia.co.uk/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) ![Laundry room](https://images.trvl-media.com/lodging/1000000/50000/43100/43087/7d3e25f0.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) ![Reception](https://images.trvl-media.com/lodging/1000000/50000/43100/43087/598f2666.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Motel 6 Winchester, VA Winchester 8.2/10 Very good (1004) "Friendly staff, spotless rooms, safe property and location. Great place for those traveling with pets." £58 includes taxes & fees 13 Oct - 14 Oct [](https://www.expedia.co.uk/Winchester-Hotels-Motel-6-Winchester.h43087.Hotel-Information) ![In-room safe, desk, iron/ironing board, free cots/infant beds](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/28616e5b.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/422ace16.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) ### Travelodge by Wyndham Winchester Winchester 8.6/10 Excellent (1082) "Excellent staff" £56 includes taxes & fees 19 Oct - 20 Oct [](https://www.expedia.co.uk/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) ![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) ![Premium Suite, 1 Queen Bed | Individually decorated, individually furnished, iron/ironing board](https://images.trvl-media.com/lodging/1000000/40000/34500/34467/b112d555.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) ### 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." £96 includes taxes & fees 13 Oct - 14 Oct [](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) ![Lobby](https://images.trvl-media.com/lodging/4000000/3900000/3893400/3893306/87742930.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) ![Exterior](https://images.trvl-media.com/lodging/4000000/3900000/3893400/3893306/943359c8.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.co.uk/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) ![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) ![Desk, soundproofing, iron/ironing board, cots/infant beds](https://images.trvl-media.com/lodging/16000000/15800000/15799900/15799885/2186fef6.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 (525) "Great pool and quiet area to stay in" £69 includes taxes & fees 13 Oct - 14 Oct [](https://www.expedia.co.uk/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) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/bff9ad76.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/d6b37fa1.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 (1014) "Very nice hotel " £107 includes taxes & fees 19 Oct - 20 Oct [](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/1000000/30000/24100/24072/9bc5a360.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) ![Breakfast area](https://images.trvl-media.com/lodging/1000000/30000/24100/24072/7b28bc9e.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 (1006) "Staff was very respectful and friendly " £46 includes taxes & fees 1 Nov - 2 Nov [](https://www.expedia.co.uk/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 curtains, iron/ironing board, free cots/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 (1016) "Staff was excellent !!! Hotel was clean and comfortable in great location !!! Would stay here again !!! " £97 includes taxes & fees 26 Oct - 27 Oct [](https://www.expedia.co.uk/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) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/16600/16597/7a3981b7.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) ![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.co.uk/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) ![Standard Room, 2 Queen Beds, Non Smoking | Hypo-allergenic bedding, down duvets, desk, iron/ironing board](https://images.trvl-media.com/lodging/1000000/900000/892900/892882/decc147c.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) ![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 (1004) "Great stay offered a haven on a long trip!" £62 includes taxes & fees 29 Oct - 30 Oct [](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=2025-10-26&endDate=2025-10-27®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 ![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.co.uk/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.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 "2 blocks from city hall/old town. Got married at city hall. Very easy and accessible and the hotel was beautiful. " [](https://expedia.co.uk/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![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 "Great location." [](https://expedia.co.uk/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.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.co.uk/Winchester-Hotels-Motel-6-Winchester.h43087.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 "Air conditioner works fine comfy bed! I have stayed here several times. Breakfast is not awesome but decent!! Coffee is awesome! :) I will stay here again" [](https://expedia.co.uk/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.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.co.uk/Winchester-Hotels-Spark-By-Hilton-Winchester.h117743.Hotel-Information) ## Frequently asked questions ### Are you looking for a luxury hotel for your Winchester holiday? > Expedia can help you arrange a flight to Martinsburg, WV (MRB-Eastern West Virginia Regional) airport or Washington Dulles International 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'd like 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 temperature of 22°C, while the coldest months are January and February, with an average of 2°C. Average annual precipitation for Winchester is 1172 mm. ### 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. 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[Flights from Chicago (ORD) to Winchester (WGO)](https://www.expedia.co.uk/lp/flights/ord/wgo/chicago-to-winchester) - [Apple Blossom Mall](https://www.expedia.co.uk/Apple-Blossom-Mall-Winchester.d6164018.Attraction) - [Barns of Rose Hill](https://www.expedia.co.uk/Barns-Of-Rose-Hill-Berryville.d553248621561864687.Attraction) - [Berryville Holidays](https://www.expedia.co.uk/Berryville.d184082.Holidays-City-Breaks) - [Visit Bluemont](https://www.expedia.co.uk/Bluemont.dx6348602) - [Boyce Holidays](https://www.expedia.co.uk/Boyce.d184084.Holidays-City-Breaks) - [Bright Box Theater](https://www.expedia.co.uk/Bright-Box-Theater-Old-Town-Winchester.d553248621561864843.Attraction) - [Dinosaur Land](https://www.expedia.co.uk/Dinosaur-Land-White-Post.d553248621532661835.Attraction) - [Visit Front Royal](https://www.expedia.co.uk/Front-Royal.dx7312) - [Visit Linden](https://www.expedia.co.uk/Linden.dx3000460101) - [Mackintosh Fruit Farm](https://www.expedia.co.uk/Mackintosh-Fruit-Farm-Berryville.d553248621532661930.Attraction) - [Shenandoah Valley Discovery Museum](https://www.expedia.co.uk/Shenandoah-Valley-Discovery-Museum-Old-Town-Winchester.d553248621587527659.Attraction) - [Winchester Medical Center](https://www.expedia.co.uk/Winchester-Medical-Center-Winchester.d6164057.Attraction) - [Visit Old Town Winchester](https://www.expedia.co.uk/Winchester-Old-Town-Winchester.dx6164092) - [Ace New Zealand Rental Cars in Riverton](https://www.expedia.co.uk/ACE-New-Zealand-Car-Rentals-In-Riverton.d553248635975849884-c1106.Car-Rental-Guide-Suppliers) - [Car hire Front Royal](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Front-Royal.d7312.Car-Hire-Guide) - [Car hire Paris](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Paris.d6050691.Car-Hire-Guide) - [Car hire in Dollar Rent A Car Bd De La Marine](https://www.expedia.co.uk/Dollar-Rent-A-Car-at-Bd-De-La-Marine-Hyeres-FRA.v12076.Car-Rental-Guide-Location) - [Front Royal Holiday Rentals](https://www.expedia.co.uk/Front-Royal-Holiday-Rentals.d7312.Travel-Guide-HolidayRentals) - 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