Title: Book the Best HISTORIC Hotels in Old Town Winchester in 2025 | 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 Historic Hotels in Old Town Winchester, VA from CA $181 ![](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 Historic Hotels Tonight [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) Tomorrow [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=6164092&startDate=2025-10-14&endDate=2025-10-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This 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) Next weekend [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 Historic Hotels ![Porch](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/17b0fc68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout drapes, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/a888dfb4.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) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/800932de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Winchester-University/Mall Area Winchester 9.0/10 Wonderful (1017) "Staff was excellent !!! Hotel was clean and comfortable in great location !!! Would stay here again !!! " CA $160 CA $181 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/64000000/63120000/63112800/63112784/13764d29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/64000000/63120000/63112800/63112784/ed3d2da3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/64000000/63120000/63112800/63112784/9641cad8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/64000000/63120000/63112800/63112784/a696274d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Bluemont Village Home Bluemont 10/10 Exceptional (36) "No need to look any further! Beautiful, clean,historic home in a perfect location. Close to wineries, breweries, Shenandoah River, hiking and only 45 minutes from DC. The host was very accommodating and friendly as well. We would highly recommend this home for you and your family. " [](https://www.expedia.ca/Winchester-Hotels-Historic-Cottage-In-Bluemont-Village-VA-Wine-Country.h63112784.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=2025-10-28&endDate=2025-10-29®ionId=6164092&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Old Town Winchester Hotel Reviews ![Hampton Inn Front Royal](//images.trvl-media.com/lodging/1000000/900000/892600/892585/75c26333_y.jpg) ### Hampton Inn Front Royal 10/10 Excellent "Room was very clean, spacious and well " [](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.Hotel-Information) ![Days Inn by Wyndham Charles Town/Harpers Ferry](//images.trvl-media.com/lodging/11000000/10630000/10620700/10620696/6feea908_y.jpg) ### Days Inn by Wyndham Charles Town/Harpers Ferry 10/10 Excellent "I" [](https://expedia.ca/Martinsburg-Hotels-Days-Inn-By-Wyndham-Charles-TownHarpers-Ferry.h10620696.Hotel-Information) ![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 "Stayed here while on a golf trip with friends. Was very please with every aspect of stay. Tex-Mex cantina adjacent to hotel was excellent food and drink without having to leave hotel. Will definitely stay there again." [](https://expedia.ca/Winchester-Hotels-Ramada-By-Wyndham-Strasburg.h1246311.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 "Was just one night with group of friends. Location was great, easy check in and out, good breakfast and comfy beds. Would highly recommend. " [](https://expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![Rodeway Inn & Suites - Charles Town, WV](//images.trvl-media.com/lodging/10000000/9870000/9868900/9868848/b6dd3662_y.jpg) ### Rodeway Inn & Suites - Charles Town, WV 10/10 Excellent "Fast check in" [](https://expedia.ca/Martinsburg-Hotels-Rodeway-Inn-Suites.h9868848.Hotel-Information) ![DoubleTree by Hilton Front Royal Blue Ridge Shadows](//images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/204cbf3a_y.jpg) ### DoubleTree by Hilton Front Royal Blue Ridge Shadows 10/10 Excellent "The hotel was clean which is the priority for me. The rooms were big, beds comfortable and amenities (hot tub) a added perk " [](https://expedia.ca/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.Hotel-Information) ![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.ca/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.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 "I love this place. Very clean. I've been to many motels in the area and they are horrible, filthy, unkempt properties. Here they have an elevator which is very easy on the legs and arms when getting one's luggage in. Very congenial owner. They don't discriminate against smokers. Other motels in the area put a smoker in rooms that weren't even cleaned. I would recommend this Travel Lodge to all types of guests. Business or leisure." [](https://expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.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 "Very nice hotel " [](https://expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ## Frequently asked questions ### What should a history enthusiast expect from a trip to Old Town Winchester? > Those who want a historical tour will not be disappointed in a trip to Old Town Winchester. While you're here, be sure to check out the shops and live music. And also relish a stop at the top-notch restaurants in this walkable area. ### How many historically relevant hotels are located in Old Town Winchester? > In Old Town Winchester, there are 12 hotel accommodations bookable on Expedia though you won't find many designated historic hotels. ### What are the most important historical places and other sights to visit in Old Town Winchester? > Old Town Winchester is notable for landmarks like George Washington's Office. Cultural venues include Bright Box Theater and Old Court House Civil War Museum. A couple of additional sights to add to your agenda are Shenandoah Valley Discovery Museum and Handley Regional Library. ### What is a historic hotel like in Old Town Winchester? > A historic hotel gives guests the opportunity to stay in a place recognized with an official historic designation. Historic hotels throughout the world can take the form of castles, stately homes, palaces or even pubs, lodges, old police stations or skyscrapers. These types of hotels in Old Town Winchester typically preserve original characteristics such as period features or traditional architecture in their public spaces or guestrooms. ### What is the difference between a historic hotel and a heritage hotel? > They are quite similar. "Historic hotel" is more commonly used in the U.S., while you'll often hear "heritage hotel" in Asia and Europe. Historic hotels tend to focus on the physical building and architecture. Heritage hotels draw their meaning mainly from the place's cultural value and how it inspired the surrounding community. ### Do historic hotels in Old Town Winchester have modern facilities? > Yes. Every effort is made to preserve the historic aspects and traditions, while interiors have safety features and modern conveniences. Guests can expect the amenities from a contemporary hotel such as private rooms with updated bathroom facilities, WiFi, and more. 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