Title: Book the Best Old Town Winchester Ski Hotels in 2025 from CA $85 | 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 $85 - ![](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 [Nov 5 - Nov 6](https://www.expedia.ca/Hotel-Search?regionId=6164092&startDate=2025-11-05&endDate=2025-11-06&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 6 - Nov 7](https://www.expedia.ca/Hotel-Search?regionId=6164092&startDate=2025-11-06&endDate=2025-11-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6164092&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=6164092&startDate=2025-11-14&endDate=2025-11-16&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 (1005) "Very nice hotel " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul CA $178 CA $202 total includes taxes & fees Nov 23 - Nov 24 [](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/b96d495c.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 Front Royal 9.0/10 Wonderful (1000) "Friendly staff, nice clean room, hotel restaurant was delicious. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dorothy CA $149 CA $168 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.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/2000000/1250000/1246400/1246311/9fcf0199.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 8.2/10 Very good (1001) "Our stay was fine, convenient location to our planned activities. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) mitchell CA $102 CA $113 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Winchester-Hotels-Ramada-By-Wyndham-Strasburg.h1246311.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/be60c3ce.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) ### Hampton Inn Winchester N/Conference Center, VA Winchester 9.2/10 Wonderful (830) "Great place to stay. Super clean and comfortable beds." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roy Allen CA $138 CA $156 total includes taxes & fees Nov 16 - Nov 17 [](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) ![Property amenity](https://images.trvl-media.com/lodging/3000000/2750000/2745600/2745505/802c0401.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) ### TownePlace Suites by Marriott Winchester Winchester 8.8/10 Excellent (470) "Nice place to stay. Great staff and breakfast." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stormy CA $151 CA $164 total includes taxes & fees Nov 7 - Nov 8 [](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) ![4 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/1087f0c8.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/a8cc2147.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 (8) "Love the view and beautiful appointed decor throughout the home…" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lynn M. CA $282 CA $610 total includes taxes & fees Nov 24 - Nov 25 [](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) ![Hallway](https://images.trvl-media.com/lodging/4000000/3190000/3182100/3182072/996fd420.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/4000000/3190000/3182100/3182072/2b84fac6.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) ### Motel 6 Front Royal, VA Front Royal 6.8/10 (496) "Quiet " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jocelyn CA $76 CA $85 total includes taxes & fees Dec 1 - Dec 2 [](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) ![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) ![Smart TV, fireplace, offices, computer monitors](https://images.trvl-media.com/lodging/88000000/87700000/87694600/87694517/e7b5a80b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain cabin near national park & wineries Linden 10/10 Exceptional (28) "Loved the location and layout. Enough space if I wanted to do a reunion with old friends. Nice kitchen and gaming/entertainment spaces as well Would love to enjoy the deck in the spring." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) wyatt w. CA $307 CA $650 total includes taxes & fees Nov 10 - Nov 11 [](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=2025-11-19&endDate=2025-11-20®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 "Great!" [](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 "Service was great!!" 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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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