Title: Book The Best Hotels in Winchester, VA for 2026 from CA $91 - Competitive Prices - 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)[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://images.trvl-media.com/place/6056879/5a1e10ca-c30d-4d41-816e-f5af84673df6/shenandoah-valley-civil-war-museum-old-courthouse-loudoun-street-winchester-virginia.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6056879/5a1e10ca-c30d-4d41-816e-f5af84673df6/shenandoah-valley-civil-war-museum-old-courthouse-loudoun-street-winchester-virginia.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 ## Go beyond your typical stay in Winchester Pet friendly [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America®ionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2026-02-04&d1=2026-02-04&endDate=2026-02-06&d2=2026-02-06&amenities=PETS) Pool [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America®ionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2026-02-04&d1=2026-02-04&endDate=2026-02-06&d2=2026-02-06&amenities=POOL) Hot tub [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America®ionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2026-02-04&d1=2026-02-04&endDate=2026-02-06&d2=2026-02-06&amenities=HOT_TUB) Spa [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America®ionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2026-02-04&d1=2026-02-04&endDate=2026-02-06&d2=2026-02-06&amenities=SPA_ON_SITE) Family friendly [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America®ionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2026-02-04&d1=2026-02-04&endDate=2026-02-06&d2=2026-02-06&travelerType=family_friendly) Cabin [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America®ionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2026-02-04&d1=2026-02-04&endDate=2026-02-06&d2=2026-02-06&lodging=CABIN) Farm [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America®ionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2026-02-04&d1=2026-02-04&endDate=2026-02-06&d2=2026-02-06&lodging=AGRITOURISM) Apart­ment [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America®ionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2026-02-04&d1=2026-02-04&endDate=2026-02-06&d2=2026-02-06&lodging=APARTMENT) Cottage [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America®ionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2026-02-04&d1=2026-02-04&endDate=2026-02-06&d2=2026-02-06&lodging=COTTAGE) Waterpark [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America®ionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2026-02-04&d1=2026-02-04&endDate=2026-02-06&d2=2026-02-06&amenities=WATER_PARK) Chalet [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America®ionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2026-02-04&d1=2026-02-04&endDate=2026-02-06&d2=2026-02-06&lodging=CHALET) Villa [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America®ionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2026-02-04&d1=2026-02-04&endDate=2026-02-06&d2=2026-02-06&lodging=VILLA) ## Check prices for these dates Tonight [Jan 21 - Jan 22](https://www.expedia.ca/Hotel-Search?regionId=6056879&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=6056879&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=6056879&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=6056879&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester hotels ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/9e66afda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/d8a75afe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/41cd029b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/ffce1877.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Winchester [](https://www.expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) Winchester 9.2/10 Wonderful (2,246 reviews) "yes, room was spotless very nice place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ROBERT CA $127 CA $138 total includes taxes & fees Jan 22 - Jan 23 [](https://www.expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/0fd2f943.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/9e37f17d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/c7da6581.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/c5cff2bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Winchester [](https://www.expedia.ca/Winchester-Hotels-Quality-Inn.h172810.Hotel-Information) Winchester 9.2/10 Wonderful (1,000 reviews) "Great stay, as usual" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary CA $114 CA $124 total includes taxes & fees Feb 20 - Feb 21 [](https://www.expedia.ca/Winchester-Hotels-Quality-Inn.h172810.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/120000/117800/117743/ac575b89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom | Living area](https://images.trvl-media.com/lodging/1000000/120000/117800/117743/5df91a0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117800/117743/b2c1f0d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/120000/117800/117743/4baca37a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spark by Hilton Winchester [](https://www.expedia.ca/Winchester-Hotels-Spark-By-Hilton-Winchester.h117743.Hotel-Information) Winchester 9.0/10 Wonderful (1,001 reviews) "Rooms was clean, staff friendly all in all great place to stay for price close to all we needed and cozy " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Frederick CA $107 CA $121 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Winchester-Hotels-Spark-By-Hilton-Winchester.h117743.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/220661a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/69b7649a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/2e837b11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/4bbed885.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ramada by Wyndham Strasburg/Shenandoah Valley [](https://www.expedia.ca/Winchester-Hotels-Ramada-By-Wyndham-Strasburg.h1246311.Hotel-Information) Strasburg 8.4/10 Very good (1,000 reviews) "Great stay everyone friendly will stay again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary K CA $105 CA $117 total includes taxes & fees Feb 18 - Feb 19 [](https://www.expedia.ca/Winchester-Hotels-Ramada-By-Wyndham-Strasburg.h1246311.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/a391dd61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/39b30783.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/2000000/1660000/1652900/1652833/f49e1754.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/b42e7086.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Inn & Suites by Radisson, Winchester, VA [](https://www.expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) Winchester 8.8/10 Excellent (1,001 reviews) "Clean efficient room with good front desk service. Convienence to Highway 81 and eateries." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chris CA $113 CA $123 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/cf4c2663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily self-serve breakfast](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/c6c8c1e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/557f4fea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/8506bf92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Winchester [](https://www.expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information) Winchester 9.4/10 Exceptional (1,098 reviews) "We have stayed here many times on our way to Massachusetts and find it perfect every time." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patsy CA $136 CA $148 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/fab1f657.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/7284efb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/e8922549.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/3eaf7092.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Microtel Inn & Suites by Wyndham Winchester [](https://www.expedia.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information) Winchester 9.2/10 Wonderful (1,439 reviews) "Clean, spacious room with friendly staff and good breakfast..... would stay there again for sure!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eleanor CA $113 CA $123 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/0de00556.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/08af73b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/f063e2e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Select Comfort beds, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/b107c420.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Winchester [](https://www.expedia.ca/Winchester-Hotels-Fairfield-Inn-Suites-By-Marriott-Winchester.h1066410.Hotel-Information) Winchester 9.0/10 Wonderful (815 reviews) "We stay here a lot and it is always consistently clean and service is great. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kim CA $128 CA $139 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Winchester-Hotels-Fairfield-Inn-Suites-By-Marriott-Winchester.h1066410.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/860000/855600/855557/10b5cc1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/860000/855600/855557/d565eb6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/860000/855600/855557/4749606b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/860000/855600/855557/a71565c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super 8 by Wyndham Front Royal Near Shenandoah National Park [](https://www.expedia.ca/Front-Royal-Hotels-Super-8-By-Wyndham-Front-Royal.h855557.Hotel-Information) Front Royal 7.6/10 Good (1,001 reviews) "Good condition " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Phillip CA $86 CA $95 total includes taxes & fees Jan 22 - Jan 23 [](https://www.expedia.ca/Front-Royal-Hotels-Super-8-By-Wyndham-Front-Royal.h855557.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1500000/1497900/1497898/1b2ad59b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1500000/1497900/1497898/723a3b2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Down comforters, Select Comfort beds, desk, laptop workspace](https://images.trvl-media.com/lodging/2000000/1500000/1497900/1497898/fa968ddc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1500000/1497900/1497898/8f242b36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Winchester [](https://www.expedia.ca/Winchester-Hotels-Courtyard-By-Marriott-Winchester.h1497898.Hotel-Information) Winchester 9.0/10 Wonderful (927 reviews) "Room was great. Staff was extremely friendly." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy CA $148 CA $161 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Winchester-Hotels-Courtyard-By-Marriott-Winchester.h1497898.Hotel-Information) ![Snack bar](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/b9c1387b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/e84bf2ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/bf8dce02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/0c5c6174.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### TRU By Hilton Winchester [](https://www.expedia.ca/Winchester-Hotels-TRU-By-Hilton-Winchester.h39493421.Hotel-Information) Winchester 9.0/10 Wonderful (789 reviews) "Clean room, good breakfast, easy check in/out." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph CA $123 CA $134 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Winchester-Hotels-TRU-By-Hilton-Winchester.h39493421.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/810f7f7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/w3840h2556x0y4-a519cf5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![50-inch LCD TV with cable channels, TV](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/6c4fd659.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/40efde4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Front Royal [](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.Hotel-Information) Front Royal 9.0/10 Wonderful (1,002 reviews) "Very nice breakfast (eggs sausage, potatoes, ...), clean lobby, and all the staff was friendly, including Beatrix. Also we appreciated the attention to a clean and warm pool room on a very cold January. Great mexican 1 mile away at Potrillo's." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) kenneth CA $135 CA $150 total includes taxes & fees Feb 15 - Feb 16 [](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/c93a366a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/8a97ffc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/636f5ae3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pillowtop beds, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/67555e67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SpringHill Suites by Marriott Winchester [](https://www.expedia.ca/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information) Winchester 9.4/10 Exceptional (799 reviews) "Great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rene CA $148 CA $161 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/19e0634f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Smoking | Living area](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/38eadba9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Smoking](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/e1711cc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Smoking | Living area](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/bf0bfb1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Travelodge by Wyndham Winchester [](https://www.expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) Winchester 8.6/10 Excellent (1,070 reviews) "Hotels well Located off 81 for a nice pull Off and overnight stay. Staff is friendly and helpful and rooms comfortable and quiet. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stefanie CA $97 CA $105 total includes taxes & fees Jan 22 - Jan 23 [](https://www.expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/40000/34400/34394/83ee60b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually furnished, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/40000/34400/34394/fde0973a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free buffet breakfast](https://images.trvl-media.com/lodging/1000000/40000/34400/34394/ef7d5b18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/40000/34400/34394/ab6f1ae4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Winchester South-Stephens City by IHG [](https://www.expedia.ca/Winchester-Hotels-Holiday-Inn-Express-Winchester-South-Stephens-City.h34394.Hotel-Information) Stephens City 8.2/10 Very good (814 reviews) "Clean room, nice staff, simple but good breakfast, fresh ground coffee machine was really nice. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rose CA $102 CA $111 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Winchester-Hotels-Holiday-Inn-Express-Winchester-South-Stephens-City.h34394.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/c68804b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed (Additional Living Area)](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/aeec97ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/ee4df7fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/7ff8d7be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Winchester Se-Historic Gateway by IHG [](https://www.expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information) Winchester 9.0/10 Wonderful (1,000 reviews) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lori CA $108 CA $122 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/1000000/40000/34500/34467/a3d72fc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/40000/34500/34467/06bbe3a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/40000/34500/34467/2f175422.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/1000000/40000/34500/34467/d6942b45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wayside Inn [](https://www.expedia.ca/Middletown-Hotels-Wayside-Inn.h34467.Hotel-Information) Middletown 9.2/10 Wonderful (420 reviews) "Historic inn. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $100 CA $124 total includes taxes & fees Jan 22 - Jan 23 [](https://www.expedia.ca/Middletown-Hotels-Wayside-Inn.h34467.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/3000000/2240000/2230900/2230885/ce971938.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/3000000/2240000/2230900/2230885/34142b17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2240000/2230900/2230885/2df64736.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2240000/2230900/2230885/e8d6877f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites Strasburg Shenandoah Valley [](https://www.expedia.ca/Winchester-Hotels-Fairfield-Inn-Suites-Strasburg-Shenandoah-Valley.h2230885.Hotel-Information) Strasburg 9.0/10 Wonderful (1,001 reviews) "We like staying here on our way south." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Catherine CA $156 CA $174 total includes taxes & fees Jan 30 - Jan 31 [](https://www.expedia.ca/Winchester-Hotels-Fairfield-Inn-Suites-Strasburg-Shenandoah-Valley.h2230885.Hotel-Information) ![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) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/31f87045.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) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/50dde1f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The George Washington Hotel, A Wyndham Grand Hotel [](https://www.expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) Old Town Winchester 9.4/10 Exceptional (1,004 reviews) "Great hotel!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) CHARLES CA $175 CA $199 total includes taxes & fees Jan 27 - Jan 28 [](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) ![Lobby](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/9cf3d079.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/d92b1c53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Front Royal Blue Ridge Shadows [](https://www.expedia.ca/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.Hotel-Information) Front Royal 9.0/10 Wonderful (1,000 reviews) "Great room and staff. Nice restaurant and bar also with good prices. Very nice hotel. 5 stars" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vincent CA $135 CA $149 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.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=6056879&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%2FWinchester-Hotels.d6056879.Travel-Guide-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Hotels.d6056879.Travel-Guide-Hotels) ## Where to stay in Winchester Winchester, Virginia, offers a delightful blend of history and scenery, making it an ideal destination for outdoor enthusiasts and urban explorers alike. Stroll through the heart of downtown Winchester, where charming shops and friendly locals create a welcoming atmosphere. Nearby, you can discover family-friendly attractions and vibrant neighborhoods, all within walking distance. Immerse yourself in the region's rich heritage while enjoying breathtaking vistas and engaging adventures throughout the Winchester area. - Old Town Winchester - Winchester Historic District ![](https://mediaim.expedia.com/destination/1/720fb116634761161ecda43d4ca150e7.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [](https://www.expedia.ca/Hotel-Search?pwaOverlay=map®ionId=6164092) ![Old Town Winchester map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:_wcnFvob%7CMwb%40aMxGad%40bc%40pLeHpd%40&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=ljIi5EMaahlKlQ6KQ_BYkQvEIhQ=) ### Old Town Winchester Nestled in the picturesque Shenandoah Valley, Old Town Winchester, Virginia, is a charming destination that offers a delightful blend of history and outdoor adventure. With peak visitor numbers during the summer months and in October, it attracts families and adventure seekers alike. Explore cultural gems like Shenandoah University and the Museum of the Shenandoah Valley, or let the kids enjoy the Shenandoah Valley Discovery Museum. Whether you're wandering historic streets or enjoying local festivities, Old Town Winchester promises an enriching and memorable experience for every traveller. [See properties](https://www.expedia.ca/Hotel-Search?regionId=6164092) ![](https://mediaim.expedia.com/destination/1/720fb116634761161ecda43d4ca150e7.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [](https://www.expedia.ca/Hotel-Search?pwaOverlay=map®ionId=918789051029594112) ![Winchester Historic District map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:ctdnFvsd%7CM%7DI_FCA%5BQeAo%40iAs%40L_%40DB%5E%7BAFDDQDUf%40NDUHBR%7D%40RFLo%40o%40Wc%40USGHeBDuADw%40HaChDM%40ETkCHcAeAG%7B%40Ew%40El%40mFFMFIFGJGHAJ%3FtA%5CRB%5CuC%5BGVwB_CaBaGgEiNmJ%3F%5B%7C%40iFi%40m%40Z%7DBDCHg%40Hq%40F_%40%40SDS%60%40LFi%40F_%40Da%40Fa%40XHR%5BHk%40Hg%40OEHg%40%3FGPgALy%40p%40R%3F_%40L%7B%40%5EJR%3Fd%40LDUBUBONDNDNDNDNDNDNDJBVHPFNBLBn%40PZYb%40L%40%3FRFTaBbAVLDJc%40%5CuBDUN%7B%40MIAAc%40KDUW%40SAK%3Fa%40G_%40KHa%40VcBFQLy%40l%40PRHPFRFCP%7EAd%40BSvA%60%40CRRFVFN%3FNDEZJBND%40%40AFJDbAXGXEXALn%40RpG%7DAf%40ICJk%40zDaFwACb%40Mx%40Kr%40ZJa%40nCd%40NbAX%5CmCTFRDhAXVmB%7C%40VFc%40v%40oFJK%60%40%3FVB%5CDb%40JnCx%40nDbAF_%40RsAT%7DA%7EBp%40hCjAh%40NlBv%40Kn%40_%40bCxA%60%40c%40lDYfBRj%40Kl%40E%5ELDEZ%3F%3FCXNDRFA%40XH%5C%3Fb%40LTFRFRFXHVRf%40NCTCLALCLCRId%40%5B%5EE%5CG%5CXJPDCPCLALCJADA%3FGASIMCGd%40Ib%40Kr%40O%60%40U%7EAHDTDRFEPCRE%5CAJERYIG%60%40Ij%40%5DXM%7C%40ZJG%5ETHABKp%40z%40V%40n%40LD%60%40LZJBM%60%40J%5EJQnAIb%40WlB%7D%40WA%3FECCNy%40Ui%40f%40%5BK%3FAOGMGA%3F%7B%40YEe%40MGq%40Q%3FABIc%40Mi%40O%5BAg%40O_%40KYIYIc%40R%5DKg%40QAJw%40WQw%40q%40Sg%40Oc%40Kc%40Ne%40O%3FDuAa%40%5D%40UIQGFe%40OE%3FBGCKAk%40QCAk%40Oi%40b%40QI%40CSEi%40ODUOES%7CAGFM%60%40QnAMEAJOp%40PFIn%40Id%40Ij%40If%40Ih%40If%40Ij%40Kh%40Gh%40If%40Kl%40Ih%40QG%3FA_ACMTWn%40Uh%40Gl%40Gn%40Id%40AH%3Fn%40%3Fv%40AXJDTx%40Yf%40p%40%5EjA%5EsE%7CY&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=DA_fdKQkDO_rSB3B7g9rdHINaU0=) ### Winchester Historic District Discover the charm of Winchester Historic District, located in the scenic Shenandoah Valley of Virginia. This vibrant neighbourhood offers a rich tapestry of history and culture, perfect for outdoor enthusiasts and families alike. Visitors flock here from July to August and in October, drawn by attractions like the historic Shenandoah University and the Museum of the Shenandoah Valley, showcasing art and history. For families, the Shenandoah Valley Discovery Museum provides engaging, hands-on experiences for children. With its unique blend of adventure and heritage, Winchester Historic District promises an unforgettable getaway. [See properties](https://www.expedia.ca/Hotel-Search?regionId=918789051029594112) ## Winchester and related destinations - Winchester - Pueblo - Staunton - Florence - Nyack Stroll through the charming pedestrian mall in the historic district, where shops and excellent restaurants await. Delve into local culture at the Museum of the Shenandoah Valley or catch a show at the Bright Box Theatre. [See all hotels in Winchester](https://www.expedia.ca/Hotel-Search?startDate=2026-02-04&endDate=2026-02-05&adults=2®ionId=6056879) ![](https://images.trvl-media.com/place/6056879/5a1e10ca-c30d-4d41-816e-f5af84673df6.jpg?impolicy=fcrop&w=900&h=566&p=1&q=high) ### Stay near popular Winchester attractions Winchester, Virginia, is an excellent destination for outdoor enthusiasts and those seeking scenic beauty. Visitors can explore historic houses and colleges, as well as enjoy leisurely activities by the lake. The area offers a rich cultural experience and family-friendly attractions, perfect for creating lasting memories during your vacation. [](https://expedia.ca/Museum-Of-The-Shenandoah-Valley-Hotels.0-l6127313-0.Travel-Guide-Filter-Hotels) ![Gardens at Glen Burnie House.](https://images.trvl-media.com/place/6056879/a8b6bc61-16a0-4bd7-8e9c-ba5025791cbb.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Museum of the Shenandoah Valley 5/5(1 review) Experience a captivating blend of art and culture at the Museum of the Shenandoah Valley, showcasing regional history and stunning landscapes in a serene setting. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6127313) [](https://expedia.ca/Jim-Barnett-Park-Hotels.0-l6164028-0.Travel-Guide-Filter-Hotels) ![Jim Barnett park](https://images.trvl-media.com/place/6056879/c975fc72-ad57-4298-afc1-a46af23cbed9.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Jim Barnett Park Enjoy tranquil walks along scenic trails, practice yoga in serene settings, and unwind at picnic spots surrounded by nature at Jim Barnett Park, perfect for relaxation and rejuvenation. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6164028) [](https://expedia.ca/Shenandoah-University-Hotels.0-l6127311-0.Travel-Guide-Filter-Hotels) #### Shenandoah University 4/5(1 review) Experience the rich culture and historic charm of Shenandoah University, where vibrant campus life and picturesque surroundings create a unique and engaging atmosphere for visitors. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6127311) [](https://expedia.ca/ValleyHealth-Winchester-Medical-Center-Hotels.0-l6164057-0.Travel-Guide-Filter-Hotels) #### ValleyHealth Winchester Medical Center Though ValleyHealth Winchester Medical Center might be what brings you to town, perhaps you'll have a chance to explore more of Winchester while you are here. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6164057) [](https://expedia.ca/Apple-Blossom-Mall-Hotels.0-l6164018-0.Travel-Guide-Filter-Hotels) #### Apple Blossom Mall Apple Blossom Mall offers a vibrant shopping experience with family-friendly stores, entertainment options, and a mix of local and brand-name shops perfect for all ages. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6164018) [](https://expedia.ca/Shenandoah-Valley-Discovery-Museum-Hotels.0-l553248621587527659-0.Travel-Guide-Filter-Hotels) #### Shenandoah Valley Discovery Museum Explore the interactive exhibits of Shenandoah Valley Discovery Museum, where families can enjoy engaging activities that celebrate the region's culture and foster a love for learning. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621587527659) ## More cheap stays in Winchester ![Baymont by Wyndham Warrenton](https://images.trvl-media.com/lodging/1000000/20000/10100/10086/ad87d83f_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Baymont by Wyndham Warrenton 7379 Comfort Inn Drive Warrenton VA CA $85 CA $91 total Jan 28 - Jan 29 includes taxes & fees 6.2/10 (1,000 reviews) [](https://expedia.ca/Warrenton-Hotels-Baymont-By-Wyndham-Warrenton.h10086.Hotel-Information) ![Travelodge by Wyndham Winchester](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/9d44a9b1_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Travelodge by Wyndham Winchester 160 Front Royal Pike Winchester VA CA $97 CA $105 total Jan 22 - Jan 23 includes taxes & fees 8.4/10 Very Good! (1,066 reviews) [](https://expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) ![Ramada by Wyndham Strasburg/Shenandoah Valley](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/08da8378_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Ramada by Wyndham Strasburg/Shenandoah Valley 21 Signal Knob Dr Strasburg VA CA $105 CA $117 total Feb 18 - Feb 19 includes taxes & fees 8.2/10 Very Good! (1,002 reviews) [](https://expedia.ca/Winchester-Hotels-Ramada-By-Wyndham-Strasburg.h1246311.Hotel-Information) ![Microtel Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/fab1f657_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Microtel Inn & Suites by Wyndham Winchester 150 Faraday Plaza Winchester VA CA $113 CA $123 total Jan 26 - Jan 27 includes taxes & fees 9/10 Wonderful! (1,438 reviews) [](https://expedia.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information) ![Hampton Inn Martinsburg](https://images.trvl-media.com/lodging/1000000/70000/63100/63064/835cd022_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hampton Inn Martinsburg 975 Foxcroft Ave Martinsburg WV CA $122 CA $138 total Jan 27 - Jan 28 includes taxes & fees 8.6/10 Excellent! (1,006 reviews) [](https://expedia.ca/Martinsburg-Hotels-Hampton-Inn-Martinsburg.h63064.Hotel-Information) ![Comfort Inn & Suites Winchester](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/cf4c2663_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Comfort Inn & Suites Winchester 195 Kernstown Commons Blvd Winchester VA CA $136 CA $148 total Feb 1 - Feb 2 includes taxes & fees 9.4/10 Exceptional! (1,095 reviews) [](https://expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information) ## Hotels in Winchester with star-rating ![5 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/25600/25559/c6e0103a_z.jpg) 5 Star Hotels 2 properties [](https://expedia.ca/5Star-Winchester-Hotels.s50-0-d6056879.Travel-Guide-Filter-Hotels) ![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/23700/23677/6ae928dd_z.jpg) 4 Star Hotels 17 properties [](https://expedia.ca/4Star-Winchester-Hotels.s40-0-d6056879.Travel-Guide-Filter-Hotels) ![3 Star Hotels](https://images.trvl-media.com/lodging/20000000/19690000/19681400/19681371/84fffc75_z.jpg) 3 Star Hotels 249 properties [](https://expedia.ca/3Star-Winchester-Hotels.s30-0-d6056879.Travel-Guide-Filter-Hotels) ![2 Star Hotels](https://images.trvl-media.com/lodging/92000000/91830000/91828000/91827910/6717a2ac_z.jpg) 2 Star Hotels 298 properties [](https://expedia.ca/2Star-Winchester-Hotels.s20-0-d6056879.Travel-Guide-Filter-Hotels) ## Find out more about Winchester ### Top reasons to visit Winchester - **Outdoor Adventures:** Winchester offers stunning scenery and recreational areas, perfect for nature lovers and adventure seekers. - **Rich Historical Heritage:** Explore historic houses and sites to immerse yourself in Winchester's fascinating past. - **Charming Downtown:** Stroll through the vibrant downtown filled with unique shops and family-friendly attractions. - **Variety of Accommodations:** From pet-friendly hotels to business-themed lodgings, there's something for every traveller. - **Scenic Lakes:** Enjoy the beautiful local lakes, ideal for relaxing and outdoor activities. ### Find great hotels in Winchester Winchester, Virginia offers a diverse selection of accommodations, catering to various preferences and needs. From pet-friendly options to business-themed hotels and LGBTQIA welcoming stays, you'll find the perfect fit for your vacation. Explore comfortable suites and star-rated hotels that provide a memorable experience in this charming town, ensuring a delightful retreat for all travellers. - **[Travelodge by Wyndham Winchester: ](https://www.expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information)** Nestled in the heart of Winchester, Travelodge by Wyndham offers a welcoming atmosphere for those travelling with pets. This motel-style lodging prioritizes comfort and convenience, making it an ideal choice for pet owners. With amenities such as pet-friendly rooms, you can enjoy your stay without leaving your furry friends behind. The property’s emphasis on a casual, laid-back experience makes it perfect for travellers seeking a relaxed getaway. - **[La Quinta Inn & Suites by Wyndham Winchester: ](https://www.expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information)** La Quinta Inn & Suites combines business and leisure in a vibrant setting. This hotel is particularly welcoming to the LGBTQIA community and provides a range of business amenities, including multiple meeting rooms and an accessible business centre. Ideal for both professionals and leisure travellers, it allows pets and offers comfortable rooms that cater to everyone. Enjoy a stay that prioritizes inclusivity and convenience, perfect for those looking to blend work with relaxation. - **Red Roof Inn Winchester, VA:** Red Roof Inn is a family-friendly hotel that welcomes both children and pets, making it a great choice for families travelling together. The property prides itself on being LGBTQIA welcoming and ensuring a comfortable stay for all guests. With amenities designed for children, including free cribs, families can rest easy knowing their needs are catered to. With pet-friendly policies and a relaxed atmosphere, this hotel ensures everyone feels at home during their stay. ### Things to do in and around Winchester Winchester, Virginia, is perfect for outdoor enthusiasts and adventure seekers, boasting stunning scenery and recreational areas. Visitors can explore top attractions, enjoy shopping centres, and experience the vibrant nightlife. Whether you're skiing or engaging in educational activities, Winchester offers a variety of experiences that cater to all interests, making it an ideal vacation destination for Canadian tourists. **Shopping** In Winchester, you can shop at [Apple Blossom Mall](https://www.expedia.ca/Apple-Blossom-Mall-Hotels.0-l6164018-0.Travel-Guide-Filter-Hotels) for a variety of stores and entertainment. [Nalls Farm Market](https://www.expedia.ca/Nalls-Farm-Market-Hotels.0-l553248621532661846-0.Travel-Guide-Filter-Hotels) offers local goods, while Apple Valley Square Shopping Center has a great selection of shops. If you're up for a drive, explore nearby towns for unique boutiques and gifts. **Recreation** Enjoy a round of golf at [Rock Harbor Golf Course](https://www.expedia.ca/Rock-Harbor-Golf-Course-Hotels.0-l553248621561864838-0.Travel-Guide-Filter-Hotels), surrounded by beautiful landscapes and a vibrant outdoor atmosphere. For relaxation, visit [Jim Barnett Park](https://www.expedia.ca/Jim-Barnett-Park-Hotels.0-l6164028-0.Travel-Guide-Filter-Hotels), where you can unwind amidst nature. Alternatively, head to [Appleland Sports Center](https://www.expedia.ca/Appleland-Sports-Center-Hotels.0-l553248621587477489-0.Travel-Guide-Filter-Hotels) for a variety of wellness activities, just 9.7km from Winchester. **Adventure** At [Summit Point Motorsports Park](https://www.expedia.ca/Summit-Point-Motorsports-Park-Hotels.0-l6164103-0.Travel-Guide-Filter-Hotels), experience the thrill of motor racing in a vibrant atmosphere, located 17.7km from Winchester. [Watermelon Park Campground](https://www.expedia.ca/Watermelon-Park-Campground-Hotels.0-l553248621532661928-0.Travel-Guide-Filter-Hotels) offers a family-friendly outdoor adventure, situated 20.9km away. For a scenic hike, [Tuckers Lane Trailhead](https://www.expedia.ca/Tuckers-Lane-Trailhead-Hotels.0-l553248633992585760-0.Travel-Guide-Filter-Hotels) awaits, 32.2km from the city, perfect for nature lovers. **Nightlife** Winchester’s nightlife offers a variety of experiences. Enjoy a show at [Bright Box Theater](https://www.expedia.ca/Bright-Box-Theater-Hotels.0-l553248621561864843-0.Travel-Guide-Filter-Hotels) or the [Winchester Little Theater](https://www.expedia.ca/Winchester-Little-Theater-Hotels.0-l6164047-0.Travel-Guide-Filter-Hotels), both exuding culture and romance. For a unique twist, venture 33.8km to the [Morgan County Observatory](https://www.expedia.ca/Morgan-County-Observatory-Hotels.0-l553248621558141373-0.Travel-Guide-Filter-Hotels) for a night of stargazing and entertainment vibes. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Booking tips and Expedia advantages for Winchester Winchester, Virginia, offers numerous ways to save during your visit. Enjoy free attractions like Shenandoah University and Mackintosh Fruit Farm, and consider walking or biking to explore the city. The best time to visit is from January to March when accommodation prices drop, with Tuesdays being the least expensive days to stay. Use Expedia to find budget-friendly hotels and combine your flight and hotel for added savings. Look for eco-certified options to support sustainability while securing great deals and unlocking travel rewards for future trips. - **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay in Winchester are January to March, where the prices are slightly lower. This is in comparison to May to June and October, where prices are slightly higher. - **The most and least expensive days on average to stay in a hotel:** The least expensive day to stay in Winchester is Tuesday. The most expensive day to stay in Winchester is Saturday. - **Find cheap hotels on Expedia:** Expedia’s search tool empowers you to set your budget, choose your desired location, and more. You can arrange your search results from lowest to highest price, making it easy to find the most affordable accommodations first. Additionally, you have the option to refine your choices by hotel category; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly hotels that you can book. - **Consider bundling your trip:** You can save money by combining your hotel stay in Winchester with your flights and activities through an Expedia package. ### Find the best attractions in Winchester Winchester, Virginia, offers a delightful blend of outdoor adventures and rich cultural experiences. Visitors can explore historic houses and sites, enjoy the scenic beauty of local lakes, and immerse themselves in the region's history. Whether you're seeking exciting family activities or a deeper understanding of Winchester's heritage, there's something for everyone in this charming city. - **[Shenandoah University: ](https://www.expedia.ca/Shenandoah-University-Hotels.0-l6127311-0.Travel-Guide-Filter-Hotels)** Immerse yourself in the vibrant culture of Shenandoah University, a historic institution in Winchester. Explore its beautiful campus, featuring historic architecture and a lively student atmosphere that reflects the region's rich educational heritage. - **[Museum of the Shenandoah Valley: ](https://www.expedia.ca/Museum-Of-The-Shenandoah-Valley-Hotels.0-l6127313-0.Travel-Guide-Filter-Hotels)** Discover the Museum of the Shenandoah Valley, an art museum that showcases the region's history and artistic talent. With diverse exhibits, gardens, and stunning collections, it's a perfect spot for art lovers and history buffs alike. - **[Shenandoah Valley Discovery Museum: ](https://www.expedia.ca/Shenandoah-Valley-Discovery-Museum-Hotels.0-l553248621587527659-0.Travel-Guide-Filter-Hotels)** A family-friendly destination, the Shenandoah Valley Discovery Museum offers interactive exhibits and engaging activities for children. It's an educational haven where families can learn about the valley's ecology and history in a fun, hands-on way. ### Best time to go to Winchester The best time to visit Winchester is dependant on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | ---------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------- | | January | 31.3°F (-0.4°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | | February | 34.7°F (1.5°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | | March | 42.3°F (5.7°C) | Light Rain | Mostly Sunny | Average | Slightly Low | | April | 52.9°F (11.6°C) | Light Rain | Mostly Sunny | Average | Average | | May | 62.4°F (16.9°C) | Light Rain | Mostly Sunny | Average | Slightly High | | June | 70.9°F (21.6°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | July | 75.9°F (24.4°C) | Light Rain | Mostly Sunny | Slightly High | Average | | August | 73.8°F (23.2°C) | Light Rain | Mostly Sunny | Average | Average | | September | 66.9°F (19.4°C) | Light Rain | Mostly Sunny | Average | Average | | October | 55.8°F (13.2°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | November | 43.5°F (6.4°C) | Light Rain | Mostly Sunny | Average | Average | | December | 36.7°F (2.6°C) | Light Rain | Mostly Sunny | Slightly Low | Average | ### The nearest major airports for your trip to Winchester When visiting Winchester, Virginia, you have a few airport options to consider. Washington Dulles International Airport ([IAD](https://www.expedia.ca/Washington-Dulles-Intl-Airport-Hotels.0-aIAD-0.Travel-Guide-Filter-Hotels)) is 67.6km away and offers several nearby accommodations, such as the 4-star [Hyatt Regency Dulles](https://www.expedia.ca/Herndon-Hotels-Hyatt-Regency-Dulles.h150.Hotel-Information), just one mile from the airport, and the [Hilton Washington Dulles Airport](https://www.expedia.ca/Herndon-Hotels-Hilton-Washington-Dulles-Airport.h27218.Hotel-Information), two miles away. Hagerstown Regional Airport ([HGR](https://www.expedia.ca/Hagerstown-Regional-Airport-Hotels.0-aHGR-0.Travel-Guide-Filter-Hotels)) is 69.2km from Winchester, with options like the Mercersburg Inn, 19.3km away, and Springhill Suites by Marriott, six miles away. Lastly, Eastern West Virginia Regional Airport (MRB) is only 29.0km from Winchester, featuring hotels like the [Hillbrook Inn](https://www.expedia.ca/Martinsburg-Hotels-Hillbrook-Inn.h3082115.Hotel-Information), 17.7km away, and Home2 Suites by Hilton, three miles away. ## Recent reviews of Winchester hotels ![Lansdowne Resort and Spa](https://images.trvl-media.com/lodging/1000000/30000/27700/27700/5ae32850_y.jpg) ### Lansdowne Resort and Spa 5/5 Excellent "The resort was in great condition and very clean. The food at Coton & Rye was good for the price. Service throughout the weekend was excellent. " A verified traveller stayed at Lansdowne Resort and Spa Posted 2 days ago [](https://expedia.ca/Leesburg-Hotels-Lansdowne-Resort-And-Spa.h27700.Hotel-Information) ![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 5/5 Excellent "Clean, spacious room with friendly staff and good breakfast..... would stay there again for sure!" A verified traveller stayed at Microtel Inn & Suites by Wyndham Winchester Posted 3 days ago [](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 5/5 Excellent "Yes!" A verified traveller stayed at Travelodge by Wyndham Winchester Posted 4 days ago [](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 5/5 Excellent "Super clean room comfy beds" A verified traveller stayed at Hampton Inn Winchester N/Conference Center, VA Posted 5 days ago [](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-NConference-Center.h424883.Hotel-Information) ![Hampton Inn Martinsburg](https://images.trvl-media.com/lodging/1000000/70000/63100/63064/835cd022_y.jpg) ### Hampton Inn Martinsburg 5/5 Excellent "Staff great, breakfast great, perfect pet stop dogs loved it!" A verified traveller stayed at Hampton Inn Martinsburg Posted 5 days ago [](https://expedia.ca/Martinsburg-Hotels-Hampton-Inn-Martinsburg.h63064.Hotel-Information) ![Quality Inn Winchester](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/0fd2f943_y.jpg) ### Quality Inn Winchester 5/5 Excellent "Conveniently located; clean floors, great pillows, and lots of parking thank you." A verified traveller stayed at Quality Inn Winchester Posted 5 days ago [](https://expedia.ca/Winchester-Hotels-Quality-Inn.h172810.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 5/5 Excellent "Clean room, reception staff very nice " A verified traveller stayed at Fairfield Inn & Suites by Marriott Winchester Posted 7 days ago [](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 5/5 Excellent "yes, room was spotless very nice place to stay" A verified traveller stayed at La Quinta Inn & Suites by Wyndham Winchester Posted 8 days ago [](https://expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![Hampton Inn Winchester-University/Mall Area](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/17b0fc68_y.jpg) ### Hampton Inn Winchester-University/Mall Area 5/5 Excellent "Pet friendly and they provided a goodie bag for my dog - very welcoming." A verified traveller stayed at Hampton Inn Winchester-University/Mall Area Posted 8 days ago [](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.Hotel-Information) ## Frequently asked questions ### What are the best hotels in Winchester with outdoor pools? > [Hampton Inn Winchester N/Conference Center, VA](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-NConference-Center.h424883.Hotel-Information) also shines in the outdoor pool category, providing a refreshing space for relaxation after a day of exploration. With a matching review score of 9.2, this hotel impresses visitors with its friendly and helpful staff, as well as its comfortable rooms. The complimentary breakfast buffet is another highlight that families appreciate, adding to the convenience of their stay. > > > For those who prefer a hotel near shopping and university areas, [Hampton Inn Winchester-University/Mall Area](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.Hotel-Information) is a solid option featuring an outdoor pool. With a traveller rating of 9.0, guests praise the staff for being friendly and amazing, while praising the clean rooms and great breakfast offerings. The location makes it superb for families looking to explore local attractions. > > > [Courtyard by Marriott Winchester](https://www.expedia.ca/Winchester-Hotels-Courtyard-By-Marriott-Winchester.h1497898.Hotel-Information), though primarily offering an indoor pool, also caters to families looking for a comfortable stay with a review score of 8.8\. Its amenities, including spacious suites and convenient self-parking, make it a practical choice for travellers. > > > Lastly, [TownePlace Suites by Marriott Winchester](https://www.expedia.ca/Winchester-Hotels-TownePlace-Suites-By-Marriott-Winchester.h2745505.Hotel-Information) features an outdoor pool and is known for its attentive staff and spotless rooms, also scoring an 8.8\. Families will appreciate the free continental breakfast and the good coffee available, ensuring a pleasant start to their day. ### How much does a hotel with outdoor pool in Winchester cost? ### Is it cheaper to book flights and a hotel in Winchester as a package? ### How can I save on a hotel in Winchester with Expedia? ### Can I cancel my hotel reservation on Expedia? ### What are the top pet-friendly hotels in Winchester? > For families traveling with pets, the [Spark by Hilton Winchester](https://www.expedia.ca/Winchester-Hotels-Spark-By-Hilton-Winchester.h117743.Hotel-Information) stands out with a review score of 9.0\. This inviting hotel allows pets and provides a range of convenient amenities such as free breakfast, a hot tub for relaxation, and complimentary toiletries. Families will appreciate the availability of cribs at no charge, ensuring a comfortable stay for little ones. > > > Another excellent option for families is the Holiday Inn Winchester Se-Historic Gateway, which also carries a review rating of 9.0\. This hotel features an indoor pool—superb for children to splash around—and offers free accommodations for kids. Its location in the historical district adds a cultural twist, allowing families to explore local attractions with ease. > > > For couples or solo travellers, the [Courtyard by Marriott Winchester](https://www.expedia.ca/Winchester-Hotels-Courtyard-By-Marriott-Winchester.h1497898.Hotel-Information), rated 8.8, offers a cozy atmosphere with spacious suites and an indoor pool, ideal for a romantic getaway or a serene escape from the daily grind. The [Hilton Garden Inn Winchester](https://www.expedia.ca/Winchester-Hotels-Hilton-Garden-Inn-Winchester.h2169428.Hotel-Information), also rated 8.8, caters to both pet owners and couples, providing suites and a range of amenities to make your stay comfortable and memorable. > > > No matter your travel purpose, Winchester offers a variety of accommodations that emphasize attentive service and quality, ensuring a stress-free planning experience for every guest. See more [pet-friendly hotels in Winchester](https://www.expedia.ca/winchester-hotels-pet-friendly-hotel.0-0-d6056879-tpetfriendlyhotel.travel-guide-filter-hotels). ### What are the best budget hotels in Winchester? > Another excellent option for families is the [SpringHill Suites by Marriott Winchester](https://www.expedia.ca/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information), also rated 9.4 by guests. This hotel offers a family-friendly atmosphere with an indoor pool superb for the kids to splash around in, along with free cribs for younger guests. The complimentary continental breakfast is a great way to start the day on the right note, ensuring everyone is fueled for the adventures ahead. > > > For those seeking a touch of elegance, [The George Washington Hotel, A Wyndham Grand Hotel](https://www.expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information), rated 9.2, offers a more upscale experience while still being accessible for families. With an on-site spa and fitness centre, it caters to couples looking for a romantic getaway, while the nearby mountain biking and skiing options appeal to adventure seekers. > > > Lastly, the [La Quinta Inn & Suites by Wyndham Winchester](https://www.expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information), with a review score of 9.2, features both indoor pool facilities and complimentary breakfast, making it a comfortable option for families. The inclusive setting and convenient amenities, such as accessible parking, cater to a wide range of travellers, ensuring everyone finds their superb fit in Winchester. View all [budget hotels in Winchester](https://www.expedia.ca/winchester-hotels-cheap-hotels.0-0-d6056879-tcheaphotels.travel-guide-filter-hotels). ### Where can I find the best nightlife in Winchester? > For a lively night out, head to the historic Old Town area, where you'll find an array of pubs, bars, and restaurants that often feature live music and entertainment. The bustling atmosphere here is superb for those looking to mingle with locals and enjoy a taste of Winchester's nightlife scene. > > > If you're in the mood for some craft brews, check out the Winchester Brew Works, a popular microbrewery where you can sample local beers in a relaxed setting. For a more refined experience, make your way to one of the wine bars, where you can unwind with a glass of Virginia wine while soaking in the quaint surroundings. ### Can I cancel my hotel reservation on Expedia? ### How can I save on a Winchester hotel booking with Expedia? ### How much is the nightly rate at a Winchester hotel? ## 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) - 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