Title: Book the Best Winchester Ski Hotels in 2026 from CA $89 | 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://images.trvl-media.com/place/6056879/5a1e10ca-c30d-4d41-816e-f5af84673df6.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6056879/5a1e10ca-c30d-4d41-816e-f5af84673df6.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 Ski Hotels Tonight [Feb 6 - Feb 7](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2026-02-06&endDate=2026-02-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 7 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2026-02-07&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2026-02-13&endDate=2026-02-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester ski hotels ![Lobby](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/220661a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Elevator](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/08da8378.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/2e837b11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/4bbed885.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ramada by Wyndham Strasburg/Shenandoah Valley [](https://www.expedia.ca/Winchester-Hotels-Ramada-By-Wyndham-Strasburg.h1246311.Hotel-Information) Strasburg 8.4/10 Very good (1,001 reviews) "Great stay everyone friendly will stay again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary K CA $103 CA $115 total includes taxes & fees Feb 15 - Feb 16 [](https://www.expedia.ca/Winchester-Hotels-Ramada-By-Wyndham-Strasburg.h1246311.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) ![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) ![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 [](https://www.expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) Old Town Winchester 9.4/10 Exceptional (1,005 reviews) "Great hotel!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) CHARLES CA $173 CA $196 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/204cbf3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/9874bc44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/4c7ae30b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/9cf3d079.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Front Royal Blue Ridge Shadows [](https://www.expedia.ca/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.Hotel-Information) Front Royal 9.0/10 Wonderful (1,000 reviews) "The staff was friendly and very helpful! The room was spotless and very clean. Would stay at this location again :)" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephanie CA $133 CA $147 total includes taxes & fees Feb 15 - Feb 16 [](https://www.expedia.ca/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/3000000/2750000/2745600/2745505/0ecd0e18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, iron/ironing board, bed sheets](https://images.trvl-media.com/lodging/3000000/2750000/2745600/2745505/c096d0d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/3000000/2750000/2745600/2745505/802c0401.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, iron/ironing board, bed sheets](https://images.trvl-media.com/lodging/3000000/2750000/2745600/2745505/b1c7d60b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### TownePlace Suites by Marriott Winchester [](https://www.expedia.ca/Winchester-Hotels-TownePlace-Suites-By-Marriott-Winchester.h2745505.Hotel-Information) Winchester 8.8/10 Excellent (486 reviews) "Nice place to stay. Great staff and breakfast." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stormy CA $155 CA $168 total includes taxes & fees Feb 11 - Feb 12 [](https://www.expedia.ca/Winchester-Hotels-TownePlace-Suites-By-Marriott-Winchester.h2745505.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/f7d693d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/c2c2b573.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/f8332737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/d80b6458.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Vue - Mountain Top hot tub overlooking the Shenandoah River [](https://www.expedia.ca/Front-Royal-Hotels-The-Vue-Mountain-Top-Hot-Tub-Overlooking-The-Shenandoah-River.h107613898.Hotel-Information) Front Royal 10/10 Exceptional (15 reviews) "We had a phenomenal stay! The view was absolutely breathtaking, and the house was well-kept and comfortable. We’re already talking about our next trip!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dan P. CA $184 CA $540 total includes taxes & fees Feb 10 - Feb 11 [](https://www.expedia.ca/Front-Royal-Hotels-The-Vue-Mountain-Top-Hot-Tub-Overlooking-The-Shenandoah-River.h107613898.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/4000000/3190000/3182100/3182072/7d19f317.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/4000000/3190000/3182100/3182072/a72bbe33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/4000000/3190000/3182100/3182072/6c6eef3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Vending machine](https://images.trvl-media.com/lodging/4000000/3190000/3182100/3182072/ef3774ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Motel 6 Front Royal, VA [](https://www.expedia.ca/Winchester-Hotels-Motel-6-Front-Royal.h3182072.Hotel-Information) Front Royal 6.8/10 (504 reviews) "Great Motel 6\. Clean and near good restaurants. Large area for walking dogs" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chris CA $80 CA $89 total includes taxes & fees Feb 28 - Mar 1 [](https://www.expedia.ca/Winchester-Hotels-Motel-6-Front-Royal.h3182072.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/88000000/87700000/87694600/87694517/10cae090.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, offices, computer monitors](https://images.trvl-media.com/lodging/88000000/87700000/87694600/87694517/6e67f714.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/88000000/87700000/87694600/87694517/8ba4a64d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/88000000/87700000/87694600/87694517/d12216cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain cabin near national park & wineries [](https://www.expedia.ca/Linden-Hotels-Mountain-Cabin-Near-National-Park-Wineries.h87694517.Hotel-Information) Linden 10/10 Exceptional (28 reviews) "The house and location were perfect for a little getaway with friends. It was very clean, and the location was great! We were very pleased with the entire experience." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer d. CA $259 CA $587 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Linden-Hotels-Mountain-Cabin-Near-National-Park-Wineries.h87694517.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/10000000/9770000/9760500/9760491/5175eb5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges](https://images.trvl-media.com/lodging/10000000/9770000/9760500/9760491/5243c98c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage (Bridal) | Living room](https://images.trvl-media.com/lodging/10000000/9770000/9760500/9760491/bf70d601.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/10000000/9770000/9760500/9760491/15ce3672.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mimslyn Inn Historic Hotels Of America [](https://www.expedia.ca/Luray-Hotels-Mimslyn-Inn-Historic-Hotels-Of-America.h9760491.Hotel-Information) Luray 9.0/10 Wonderful (1,003 reviews) "Perfect stay will stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) EDWARD CA $114 CA $141 total includes taxes & fees Feb 18 - Feb 19 [](https://www.expedia.ca/Luray-Hotels-Mimslyn-Inn-Historic-Hotels-Of-America.h9760491.Hotel-Information) ![Indoor pool, open 8 AM to 10 PM, sun loungers](https://images.trvl-media.com/lodging/4000000/3030000/3025100/3025089/79c45bf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/4000000/3030000/3025100/3025089/a3047346.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3030000/3025100/3025089/53fbbcfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/4000000/3030000/3025100/3025089/2a5460b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Woodstock, VA [](https://www.expedia.ca/Luray-Hotels-Hampton-Inn-Suites-Woodstock.h3025089.Hotel-Information) Woodstock 8.8/10 Excellent (1,000 reviews) "The hotel is clean, people are friendly and helpful " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alan CA $127 CA $143 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Luray-Hotels-Hampton-Inn-Suites-Woodstock.h3025089.Hotel-Information) ![Desk, cribs/infant beds, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/20000/10900/10897/d017c28b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/10900/10897/5bc9bae7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/10900/10897/d9067830.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee service](https://images.trvl-media.com/lodging/1000000/20000/10900/10897/dbad721d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Motel 6 Mount Jackson, VA - Shenandoah [](https://www.expedia.ca/Luray-Hotels-Motel-6-Mount-Jackson.h10897.Hotel-Information) Mount Jackson 7.8/10 Good (1,000 reviews) "Decent stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Disha CA $84 CA $92 total includes taxes & fees Feb 7 - Feb 8 [](https://www.expedia.ca/Luray-Hotels-Motel-6-Mount-Jackson.h10897.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=2026-02-20&endDate=2026-02-21®ionId=6056879&adults=2&location_highlights_explore=ski&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at ski hotels in Winchester Resort 4 stars 5 stars Spa Family-friendly ## Top Winchester Hotel Reviews ![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 "Clean nice room Great location for restaurants " [](https://expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ## Frequently asked questions ### What are the top-rated ski hotels in Winchester? > The 3.5-star [The George Washington Hotel, A Wyndham Grand Hotel](https://www.expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information), boasts a superb 9.4 rating and offers convenient access to both downhill and cross-country skiing opportunities. Guests also appreciate the comfortable and clean rooms. > > > With a 9.2 rating, the Hampton Inn Winchester N/Conference Center, VA provides a complimentary buffet breakfast to fuel your ski days and is situated near local ski areas. Many guests praise the friendly and helpful staff. > > > The 3-star TownePlace Suites by Marriott Winchester, rated 8.8, is located close to downhill skiing and offers a free continental breakfast. Additionally, it features both an indoor and outdoor pool, which can be a welcome amenity after a day on the slopes. ### How much does a ski hotel in Winchester cost? ### What ski hotels in Winchester are best for families? > The 3.5-star George Washington Hotel, a Wyndham Grand Hotel, rated 9.4, is a great option for families with its comfortable and clean rooms, and it provides free cots upon request. The hotel also offers free WiFi and is conveniently located near both cross-country and downhill ski areas. > > > The Hampton Inn Winchester N/Conference Center, VA, with a 9.2 rating, provides families with a complimentary buffet breakfast each morning, ensuring a good start to a day on the slopes. The hotel also has free WiFi and is situated close to ski locations. > > > The 3-star TownePlace Suites by Marriott Winchester, with an 8.8 rating, offers families the convenience of free continental breakfast and self-parking. Guests can also enjoy the outdoor pool, which can be a fun activity after a day of skiing, and it's near downhill ski options. ### Is Winchester good for skiing? > For those looking for a winter sports experience, Winchester is a practical choice because it's within a reasonable driving distance of multiple resorts. You'll find resorts offering downhill skiing, snowboarding, and sometimes tubing, typically within a 1 to 2-hour drive. This makes it an ideal spot for couples or families who want to combine a historical trip to Winchester with a day or two on the slopes. > > > Families, in particular, will appreciate Winchester as a base. After a day of skiing, you can return to a wider range of dining and accommodation options than you might find directly at the resorts, many of which are geared towards a more relaxed evening. ### Which area of Winchester is best to stay in for skiing? > Staying along US-50 in eastern Winchester offers convenient access to the main routes leading to the ski resorts. This area has a good selection of hotels and amenities, making it a practical base for skiers. You'll find a variety of dining options and shops for any last-minute needs before heading to the slopes. > > > Front Royal, a short drive south-east of Winchester, is another excellent option. It's closer to some of the prominent ski resorts and provides a more direct route to the mountains. This town offers a selection of accommodation, often at a good value, and maintains a pleasant, small-town atmosphere. ### Is it cheaper to book flights and a ski hotel in Winchester as a package? ### What dining options are typically available in Winchester ski accommodations? > This area is the heart of Winchester, known for its pedestrian-friendly Loudoun Street Walking Mall, which is lined with independent shops, restaurants, and historic buildings dating back to the 18th century. You'll find many of the city's main attractions here, including the Handley Regional Library and the Old Town Hall. It's very walkable and provides a central base for exploring. > > > Couples will find Old Town particularly appealing for its romantic setting and diverse dining options. Many of the city's best restaurants, from casual bistros to fine dining establishments, are located along the Walking Mall or just off it, making evening strolls and dinner plans effortless. The area also offers a selection of independent boutiques and art galleries for leisurely browsing. > > > For travellers interested in history and culture, Old Town is an excellent choice. It provides easy access to several museums and historic homes, such as the George Washington's Office Museum and the Stonewall Jackson's Headquarters Museum, all within a short walk. ### What activities should we do in Winchester besides skiing? > This area is the heart of Winchester, known for its pedestrian-friendly Loudoun Street, which is lined with independently owned shops, restaurants, and centuries-old architecture. You'll find landmarks like the Handley Regional Library and the Old Court House here, all within a compact and easily navigable space. > > > Couples often find Old Town ideal for a relaxing getaway. You can spend your days browsing the boutiques, enjoying meals at various eateries, and visiting historic sites such as George Washington's Office Museum or the Museum of the Shenandoah Valley. Evenings can be spent enjoying a show at the Bright Box Theater or simply strolling hand-in-hand along the lit-up mall. > > > For those interested in history, the Old Town offers easy access to multiple Civil War battlefields and museums, including the Shenandoah Valley Civil War Museum and the Third Winchester Battlefield. ### How can I save on a ski hotel in Winchester with Expedia? ### Can I cancel my ski hotel reservation on Expedia? ## 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) - 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