Title: Book the Best Old Town Winchester Ski Hotels in 2025 from CA $84 | Expedia.ca [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)[Old Town Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Old-Town-Winchester.d6164092.Car-Rental-Guide)[Old Town Winchester Vacations](https://expedia.ca/Old-Town-Winchester.d6164092.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/720fb116634761161ecda43d4ca150e7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Ski Hotels in Old Town Winchester, VA from CA $84 ![](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 Old Town Winchester Ski Hotels Tonight [Oct 12 - Oct 13](https://www.expedia.ca/Hotel-Search?regionId=6164092&startDate=2025-10-12&endDate=2025-10-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=6164092&startDate=2025-10-13&endDate=2025-10-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6164092&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6164092&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Old Town Winchester Ski Hotels ![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 (1014) "Very nice hotel " CA $177 CA $201 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![Elevator](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/08da8378.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/e47a228e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/be9a8325.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/9ef74ac2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ramada by Wyndham Strasburg/Shenandoah Valley Strasburg 8.4/10 Very good (1022) "Everyone was very friendly and it was a nice and quiet hotel. Convenient to everywhere we had wanted to go." CA $113 CA $126 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Winchester-Hotels-Ramada-By-Wyndham-Strasburg.h1246311.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/2000000/1890000/1889100/1889081/9cf3d079.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) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/ad5604d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Front Royal Blue Ridge Shadows Front Royal 9.0/10 Wonderful (1005) "The hotel was clean which is the priority for me. The rooms were big, beds comfortable and amenities (hot tub) a added perk " CA $160 CA $180 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.Hotel-Information) ![Snack bar](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/cba33bb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/b2c8e1ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/e77a1d0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/be60c3ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Winchester N/Conference Center, VA Winchester 9.2/10 Wonderful (815) "Stayed for one night with my family, the room was very clean and breakfast in the morning was really good with different options. I would book this hotel again." CA $148 CA $168 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-NConference-Center.h424883.Hotel-Information) ![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) ![32-inch flat-screen TV with digital channels, TV, Netflix](https://images.trvl-media.com/lodging/3000000/2750000/2745600/2745505/7c860f3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/3000000/2750000/2745600/2745505/0ecd0e18.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) ### TownePlace Suites by Marriott Winchester Winchester 8.8/10 Excellent (464) "Nice place to stay. Great staff and breakfast." CA $150 CA $163 total includes taxes & fees Oct 14 - Oct 15 [](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/a69388d0.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/108000000/107620000/107613900/107613898/45164b22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/323efc93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Vue - Mountain top hot tub overlooking the Shenandoah River Front Royal 9.8/10 Exceptional (7) "Love the view and beautiful appointed decor throughout the home…" CA $293 CA $619 total includes taxes & fees Nov 4 - Nov 5 [](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/fd0e8e90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Vending machine](https://images.trvl-media.com/lodging/4000000/3190000/3182100/3182072/eeb35d3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/4000000/3190000/3182100/3182072/c230fecf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/4000000/3190000/3182100/3182072/996fd420.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Motel 6 Front Royal, VA Front Royal 6.8/10 (492) "Good place to stay for a quick overnight. Nice room." CA $76 CA $84 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Winchester-Hotels-Motel-6-Front-Royal.h3182072.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/88000000/87700000/87694600/87694517/15fbac8a.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) ![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/fb3e185f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain cabin near national park & wineries Linden 10/10 Exceptional (28) "You will not be disappointed in this gem. Perfect for day trips to the National Forest or the nation’s capital. Or just enjoy the beautiful scenery. Hosts bend over backwards to accommodate you. " CA $277 CA $598 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Linden-Hotels-Mountain-Cabin-Near-National-Park-Wineries.h87694517.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=2025-10-27&endDate=2025-10-28®ionId=6164092&adults=2&location_highlights_explore=ski&sort=RECOMMENDED&openPlayBack=true) ## Top Old Town Winchester Hotel Reviews ![Ramada by Wyndham Strasburg/Shenandoah Valley](//images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/08da8378_y.jpg) ### Ramada by Wyndham Strasburg/Shenandoah Valley 10/10 Excellent "The room was perfect for a one night stay while passing through the area. The room was clean, the bed was comfortable and the location was convenient. Check in was fast and easy." [](https://expedia.ca/Winchester-Hotels-Ramada-By-Wyndham-Strasburg.h1246311.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. 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[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) - 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