Title: Hotels by Red Roof Inn in Old Town Winchester from CA $105 | Expedia.ca [Old Town Winchester Travel Guide](https://expedia.ca/Winchester-Old-Town-Winchester.dx6164092)[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) ![The Courthouse in Winchester, Virginia.](https://images.trvl-media.com/place/6164092/74e89cff-4502-4b70-84ac-0bb3e6917b82.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6164092/74e89cff-4502-4b70-84ac-0bb3e6917b82.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 prices for these dates Tonight [Jan 21 - Jan 22](https://www.expedia.ca/Hotel-Search?regionId=6164092&startDate=2026-01-21&endDate=2026-01-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 22 - Jan 23](https://www.expedia.ca/Hotel-Search?regionId=6164092&startDate=2026-01-22&endDate=2026-01-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=6164092&startDate=2026-01-23&endDate=2026-01-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=6164092&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Old Town Winchester Red Roof Inn ![Desk, blackout drapes, free cribs/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) ![Breakfast area](https://images.trvl-media.com/lodging/1000000/30000/24100/24072/7b28bc9e.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/1000000/30000/24100/24072/4ef3053b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Red Roof Inn Winchester, VA [](https://www.expedia.ca/Winchester-Hotels-Red-Roof-Inn-Winchester.h24072.Hotel-Information) Winchester 7.4/10 Good (1,001 reviews) "Clean, pet friendly and great check in." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anita Willsie CA $96 CA $105 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Winchester-Hotels-Red-Roof-Inn-Winchester.h24072.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=2026-02-04&endDate=2026-02-05®ionId=6164092&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FOld-Town-Winchester-Winchester-Hotels-Red-Roof-Inn.0-n6164092-0--bRedRoofInn.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FOld-Town-Winchester-Winchester-Hotels-Red-Roof-Inn.0-n6164092-0--bRedRoofInn.Travel-Guide-Filter-Hotels) ## Top Old Town Winchester Hotel Reviews ![Microtel Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/fab1f657_y.jpg) ### Microtel Inn & Suites by Wyndham Winchester 10/10 Excellent "Clean, spacious room with friendly staff and good breakfast..... would stay there again for sure!" [](https://expedia.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.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 "Yes!" [](https://expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) ![Hampton Inn Winchester N/Conference Center, VA](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/cba33bb0_y.jpg) ### Hampton Inn Winchester N/Conference Center, VA 10/10 Excellent "Super clean room comfy beds" [](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-NConference-Center.h424883.Hotel-Information) ![Quality Inn Winchester](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/0fd2f943_y.jpg) ### Quality Inn Winchester 10/10 Excellent "Conveniently located; clean floors, great pillows, and lots of parking thank you." [](https://expedia.ca/Winchester-Hotels-Quality-Inn.h172810.Hotel-Information) ![TownePlace Suites by Marriott Front Royal](https://images.trvl-media.com/lodging/37000000/36350000/36342700/36342604/0776aa15_y.jpg) ### TownePlace Suites by Marriott Front Royal 10/10 Excellent "Clean room, friendly and helpful staff, good breakfast, I would stay again." [](https://expedia.ca/Winchester-Hotels-TownePlace-Suites-By-Marriott-Front-Royal.h36342604.Hotel-Information) ![Ramada by Wyndham Strasburg/Shenandoah Valley](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/08da8378_y.jpg) ### Ramada by Wyndham Strasburg/Shenandoah Valley 10/10 Excellent "Breakfast isn’t bad at all eggs and sausage, apple or oj" [](https://expedia.ca/Winchester-Hotels-Ramada-By-Wyndham-Strasburg.h1246311.Hotel-Information) ![DoubleTree by Hilton Front Royal Blue Ridge Shadows](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/204cbf3a_y.jpg) ### DoubleTree by Hilton Front Royal Blue Ridge Shadows 10/10 Excellent "Great room and staff. Nice restaurant and bar also with good prices. Very nice hotel. 5 stars" [](https://expedia.ca/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.Hotel-Information) ![Fairfield Inn & Suites by Marriott Winchester](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/w4000h2662x0y0-b556d792_y.jpg) ### Fairfield Inn & Suites by Marriott Winchester 10/10 Excellent "Clean room, reception staff very nice " [](https://expedia.ca/Winchester-Hotels-Fairfield-Inn-Suites-By-Marriott-Winchester.h1066410.Hotel-Information) ![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 "yes, room was spotless very nice place to stay" [](https://expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ## Find out more about Old Town Winchester ## Old Town Winchester Hotels Guide Expedia.ca offers a selection of 366 hotels in Old Town Winchester. You are sure to find cheap deals and discount rates among them with our Best Price Guarantee. No matter what type of hotel strikes your fancy, we will let you search for your preferred one to accommodate your travel needs. Expedia.ca will not only save you time, but also money when booking your stay at a hotel in Old Town Winchester. Making reservations so you can stay within your budget is easy with us. Expedia.ca even provides you with a map so you may find hotels in the Old Town Winchester neighborhood you prefer. Go ahead. 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