Title: Book the Best HISTORIC Hotels in Winchester in 2025 | 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://mediaim.expedia.com/destination/1/720fb116634761161ecda43d4ca150e7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Historic Hotels in Winchester, VA from CA $147 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 Historic Hotels Tonight [Oct 1 - Oct 2](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-10-01&endDate=2025-10-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 2 - Oct 3](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-10-02&endDate=2025-10-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top 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) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/16920465.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) ### Hampton Inn Winchester-University/Mall Area Winchester 9.0/10 Wonderful (1001) "Price, Clean!,great breakfast, attention to details and nice room, loved it!" CA $148 CA $168 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.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) ![Lobby](https://images.trvl-media.com/lodging/10000000/9770000/9760500/9760491/15ce3672.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception hall](https://images.trvl-media.com/lodging/10000000/9770000/9760500/9760491/6addc16c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges](https://images.trvl-media.com/lodging/10000000/9770000/9760500/9760491/ff235a45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mimslyn Inn Historic Hotels Of America Luray 9.0/10 Wonderful (1020) "Wonderful property, would stay there again " CA $141 CA $175 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Luray-Hotels-Mimslyn-Inn-Historic-Hotels-Of-America.h9760491.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34830000/34821800/34821722/9c1d9621.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34830000/34821800/34821722/0f0c1ef0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/35000000/34830000/34821800/34821722/1a9ef301.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34830000/34821800/34821722/80506691.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ❤️ Secluded 1940s Romantic Tiny House on the River Shepherdstown 10/10 Exceptional (61) "We truly loved this location and definitely will be back!" CA $56 CA $147 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Martinsburg-Hotels-Secluded-1940s-Romantic-Tiny-House-On-The-River.h34821722.Hotel-Information) ![Fireplace](https://images.trvl-media.com/lodging/7000000/6850000/6846200/6846102/ac66fb6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/7000000/6850000/6846200/6846102/08345073.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/7000000/6850000/6846200/6846102/a13d0db6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Buffet breakfast for a fee on weekdays](https://images.trvl-media.com/lodging/7000000/6850000/6846200/6846102/3973dc29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Airlie Hotel Warrenton 8.8/10 Excellent (319) "We love the old charm this hotel offers, while the rooms are cozy and new!" CA $187 CA $226 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Warrenton-Hotels-Airlie-Hotel.h6846102.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/114000000/113640000/113638100/113638012/4a01e972.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/114000000/113640000/113638100/113638012/2ddc1017.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113640000/113638100/113638012/82963c99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/114000000/113640000/113638100/113638012/183f1019.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Creekside Cottage: Downtown | Pet-Friendly Shepherdstown 10/10 Exceptional (2) "Great place to stay" CA $306 CA $503 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Shepherdstown-Hotels-The-Creekside-Cottage-Downtown-Pet-Friendly.h113638012.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/23000000/22260000/22255700/22255620/f116a78a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/23000000/22260000/22255700/22255620/d3498518.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/23000000/22260000/22255700/22255620/08441d4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/23000000/22260000/22255700/22255620/2dc032bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### "Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA. Rileyville 10/10 Exceptional (328) "Place was beautiful and lived up to the name Solitude. Spent our honeymoon in perfect bliss. Great location to get away. " CA $225 CA $388 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Rileyville-Hotels-Solitude-Spectacular-1-BR-Cabin-W-Hot-Tub-Near-Luray.h22255620.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/89000000/88210000/88205300/88205213/a2cdbfd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/89000000/88210000/88205300/88205213/16ee56a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/89000000/88210000/88205300/88205213/ff062017.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/89000000/88210000/88205300/88205213/8bb88bf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic apartment in Old Town Warrenton, Virginia Warrenton 9.8/10 Exceptional (54) "Love the 5 minute walk to restaurants! Also loved staying in an apartment in a historic house. Very nicely furnished and had everything we needed. " CA $212 CA $324 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Warrenton-Hotels-Historic-Apartment-In-Old-Town-Warrenton.h88205213.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/22000000/21480000/21478100/21478041/3b7c41d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/22000000/21480000/21478100/21478041/aa284bd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/22000000/21480000/21478100/21478041/310143cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/22000000/21480000/21478100/21478041/ae9584d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### "The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA Rileyville 9.8/10 Exceptional (300) "Clean, neat and well equipped chalet. The views were lovely " CA $219 CA $379 total includes taxes & fees Oct 2 - Oct 3 [](https://www.expedia.ca/Rileyville-Hotels-The-Chalet-Shenandoah-Valley-Getaway-W-Hot-Tub-Near-Luray.h21478041.Hotel-Information) ![TV](https://images.trvl-media.com/lodging/70000000/69690000/69682500/69682460/32a9ddd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/70000000/69690000/69682500/69682460/b4424dcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/70000000/69690000/69682500/69682460/8f8250bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Floor plan](https://images.trvl-media.com/lodging/70000000/69690000/69682500/69682460/5bb6e412_edited_4e8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Downtown: Explore Shepherdstown from cozy 1br apartment Shepherdstown 9.4/10 Exceptional (16) "We were lucky to find this perfectly located place! Very clean, well-stocked with coffee in the nice kitchen, good bed. If it had reading lamps by the bed and the sofa, and more hooks/rods in the bathroom for towels, it would have been perfection. I would stay there again." CA $167 CA $281 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Shepherdstown-Hotels-Downtown-Explore-Shepherdstown-From-Cozy-1br-Apartment.h69682460.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/40000000/39540000/39532100/39532065/baa1c471.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/40000000/39540000/39532100/39532065/a816723a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/40000000/39540000/39532100/39532065/3166dbe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/40000000/39540000/39532100/39532065/99c8f223.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment The Plains 10/10 Exceptional (5) "Absolutely loved our stay at Unicorn Hollow. So peaceful. Clean and had everything you needed. Loved the horses and Guiseppe (the donkey) along with the deer and alpacas. Can stroll about the property. Anna and Pino were wonderful to meet. " CA $345 CA $550 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Marshall-Hotels-Private-Unicorn-Hollow-AptWineries-Twilight-PoloMiddleburg.h39532065.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=2025-10-15&endDate=2025-10-16®ionId=6056879&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Winchester Hotel Reviews ![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 "Convenient off I-81, clean, quiet,nice warm breakfast, even great dark roast coffee. Will definitely make this a stop on our way south annually" [](https://expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![Holiday Inn Winchester Se-Historic Gateway by IHG](//images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/c68804b2_y.jpg) ### Holiday Inn Winchester Se-Historic Gateway by IHG 10/10 Excellent "The room was spacious. " [](https://expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information) ![Quality Inn Winchester](//images.trvl-media.com/lodging/1000000/180000/172900/172810/0fd2f943_y.jpg) ### Quality Inn Winchester 10/10 Excellent "Spacious room, CLEAN comfortable beds and a good breakfast. A very good value!" [](https://expedia.ca/Winchester-Hotels-Quality-Inn.h172810.Hotel-Information) ![Hampton Inn Winchester N/Conference Center, VA](//images.trvl-media.com/lodging/1000000/430000/424900/424883/cba33bb0_y.jpg) ### Hampton Inn Winchester N/Conference Center, VA 10/10 Excellent "Clean, comfortable, lovely staff, above-average breakfast. Will stay again!" [](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-NConference-Center.h424883.Hotel-Information) ![Country Inn & Suites by Radisson, Winchester, VA](//images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/d0690cde_y.jpg) ### Country Inn & Suites by Radisson, Winchester, VA 10/10 Excellent "Loca" [](https://expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.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 "We needed a break with a long family care situation. We took a break and stayed in Winchester and relaxed. Hampton Inn was just perfect. Breakfast was great! Thank you! " [](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.Hotel-Information) ![Courtyard by Marriott Winchester](//images.trvl-media.com/lodging/2000000/1500000/1497900/1497898/8f242b36_y.jpg) ### Courtyard by Marriott Winchester 10/10 Excellent "Beautiful and comfortable room, which was very quiet and very clean. I would definitely stay here again and would recommend it to anyone. Our only issue was an electrical outlet in the bathroom that did not work. The front desk put in an immediate request for maintenance to fix it. Other than that, it was a perfect day." [](https://expedia.ca/Winchester-Hotels-Courtyard-By-Marriott-Winchester.h1497898.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 "Restaurants were nearby and there was plenty of room to walk my dog. The staff was efficient and pleasant. The room felt humid to me. Some maintenance leftovers are sitting around in the back of the property. Overall, nice place to stay but needs some TLC." [](https://expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) ![Motel 6 Winchester, VA](//images.trvl-media.com/lodging/1000000/50000/43100/43087/f87cf676_y.jpg) ### Motel 6 Winchester, VA 10/10 Excellent "I flew in from Dallas. My mother was hospitalized there. This motel was very convient for me… not far from the hospital & the price. My room was extremely clean. The staff working up front was very nice. Checked me quickly. I highly recommend this motel! " [](https://expedia.ca/Winchester-Hotels-Motel-6-Winchester.h43087.Hotel-Information) ## Frequently asked questions ### What should I expect on my historical trip to Winchester? > Visitors love the fascinating history they can explore on a trip to Winchester. The array of shops and top-notch restaurants are some of the places to visit while you're here. You can also discover the theater scene during your vacation in this family-friendly area. ### What's the best hotel in Winchester to be near historical sites? > Based on our travel expertise, [Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed](https://www.expedia.ca/Winchester-Hotels-Peaceful-Secret-Gardens-Tiny-Home-Loft-Stairs-Lead-To-A-Queen-Size-Bed.h36621280.Hotel-Information) is a top guesthouse on Expedia for those interested in history, and it features onsite laundry facilities and in-room kitchens. Patsy Cline Historic House is a short 4-minute drive away. A couple of other options to soak up the local history include [Secret Gardens Carriage House](https://www.expedia.ca/Winchester-Hotels-Find-The-Secrets-To-Peace-And-Beauty-Here.h27116696.Hotel-Information) and [ANS Inn has clean, spacious rooms located on 5 acres with little traffic.](https://www.expedia.ca/Winchester-Hotels-Vrbo-Property.h44780625.Hotel-Information). ### How many historically relevant hotels will I find in Winchester? > In Winchester, you'll find 78 hotel accommodations bookable on Expedia, including 4 designated as historic hotels or close to historic sites. ### What are the top historical sites and other places in Winchester? > Winchester is notable for landmarks like Patsy Cline Historic House, Stonewall Jackson's Headquarters, and Abram's Delight. Cultural venues include Bright Box Theater, Winchester Little Theater, and Museum of the Shenandoah Valley. A couple of additional sights to add to your agenda are Shenandoah Valley Discovery Museum and Apple Blossom Mall. ### What is a historic hotel like in Winchester? > Guests who choose a historic hotel can stay someplace that has a national historic designation. A palace, castle, grand home or even an old police station, pub, lodge, or skyscraper can be identified as a historic hotel provided that it's of special interest. Traditional architecture and period features are often found in the public spaces and guestrooms of historic hotels in Winchester, giving a historical feel. ### What is the difference between a historic hotel and a heritage hotel? > They are quite similar. "Historic hotel" is a term often used in the U.S., whereas "heritage hotel" is common in Asia and Europe. Historic hotels tend to place more significance on the building and architecture itself. Heritage hotels draw their meaning mainly from the cultural value and how it shaped the community. ### Do historic hotels in Winchester have modern facilities? > Yes, every effort is made to preserve treasured traditions and historic facades, but hotel interiors are fitted with modern conveniences and safety features. Visitors should expect the popular amenities you'd get from a hotel such as private rooms with updated bathroom facilities, WiFi, and more. When you book a historic hotel in Winchester, it doesn't mean you will stay in a place that's rundown or uncomfortable for guests. ## 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) - [Luxury Hotels in Berryville](https://www.expedia.ca/Berryville-Hotels-Luxury-Hotel.0-0-d184082-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Berryville Hotels](https://www.expedia.ca/Berryville-Hotels.d184082.Travel-Guide-Hotels) - 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[Flights from Syracuse (SYR) to Winchester (WGO)](https://www.expedia.ca/lp/flights/syr/wgo/syracuse-to-winchester) - [Flights from Calgary (YYC) to Winchester (WGO)](https://www.expedia.ca/lp/flights/yyc/wgo/calgary-to-winchester) - [Flights from Toronto (YYZ) to Winchester (WGO)](https://www.expedia.ca/lp/flights/yyz/wgo/toronto-to-winchester) - [Appleland Sports Center](https://www.expedia.ca/Appleland-Sports-Center-Stephens-City.d553248621587477489.Vacation-Attraction) - [Jim Barnett Park](https://www.expedia.ca/Jim-Barnett-Park-Winchester.d6164028.Vacation-Attraction) - [Visit Millwood](https://www.expedia.ca/Millwood.dx3000460156) - [Book Historic Hotels in Winchester on Expedia.com](https://www.expedia.com/Winchester-Hotels-Historic-Hotel.0-0-d6056879-tHistoricHotel.Travel-Guide-Filter-Hotels)