Title: 10 Best Hotels in Old Town Winchester, Winchester for 2026 | 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) ![Handley Library ](https://images.trvl-media.com/place/6056879/dd3561a1-54d7-46cf-9e70-15a3b654b5eb.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Tina McClelland # Hotels in Old Town Winchester, Winchester - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Tonight [Dec 27 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6164092&startDate=2025-12-27&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 28 - Dec 29](https://www.expedia.ca/Hotel-Search?regionId=6164092&startDate=2025-12-28&endDate=2025-12-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6164092&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=6164092&startDate=2026-01-09&endDate=2026-01-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Old Town Winchester hotels ![2 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5a07226c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5707228d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/a8e7d0d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/d6b37fa1.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 (1007) "Great hotel!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) CHARLES CA $173 CA $196 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.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/58000000/57960000/57958300/57958244/6a36301f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/e46c3593.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/f8e3941a.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) 7.8 km from Old Town Winchester 9.4/10 Exceptional (1086) "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 $132 CA $143 total includes taxes & fees Jan 25 - Jan 26, 2026 [](https://www.expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information) ![2 bars/lounges, sports bar](https://images.trvl-media.com/lodging/10000000/9870000/9868900/9868848/b6dd3662.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/10000000/9870000/9868900/9868848/56958e5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/10000000/9870000/9868900/9868848/14125876.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/10000000/9870000/9868900/9868848/64e72433.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rodeway Inn & Suites Charles Town [](https://www.expedia.ca/Martinsburg-Hotels-Rodeway-Inn-Suites.h9868848.Hotel-Information) 29.7 km from Old Town Winchester 8.6/10 Excellent (1000) "Certainly will stay again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) philip CA $87 CA $98 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Martinsburg-Hotels-Rodeway-Inn-Suites.h9868848.Hotel-Information) ![Premium bedding, pillowtop beds, desk, blackout drapes](https://images.trvl-media.com/lodging/11000000/10630000/10620700/10620696/6feea908.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/11000000/10630000/10620700/10620696/5a90060e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/11000000/10630000/10620700/10620696/9b09e95c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/11000000/10630000/10620700/10620696/cb7df1a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Days Inn by Wyndham Charles Town/Harpers Ferry [](https://www.expedia.ca/Martinsburg-Hotels-Days-Inn-By-Wyndham-Charles-TownHarpers-Ferry.h10620696.Hotel-Information) 29.6 km from Old Town Winchester 8.0/10 Very good (1001) "Nice place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cynthia CA $91 CA $103 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Martinsburg-Hotels-Days-Inn-By-Wyndham-Charles-TownHarpers-Ferry.h10620696.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/77000000/76880000/76876900/76876848/fd85fd97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/77000000/76880000/76876900/76876848/a984ecc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/77000000/76880000/76876900/76876848/29d89638.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/77000000/76880000/76876900/76876848/6a9fc093.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Charles Town - Hollywood Casino [](https://www.expedia.ca/Charles-Town-Hotels-The-Inn-At-Charles-Town.h76876848.Hotel-Information) 30 km from Old Town Winchester 8.6/10 Excellent (530) "Friendly staff, comfortable bed, convenient location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kourtney CA $154 CA $187 total includes taxes & fees Jan 12 - Jan 13, 2026 [](https://www.expedia.ca/Charles-Town-Hotels-The-Inn-At-Charles-Town.h76876848.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/4000000/3090000/3082200/3082115/eaa4b7cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/4000000/3090000/3082200/3082115/46449a17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (The Bamford Suite)](https://images.trvl-media.com/lodging/4000000/3090000/3082200/3082115/50b1e67b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/4000000/3090000/3082200/3082115/f8c19c35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hillbrook Inn [](https://www.expedia.ca/Martinsburg-Hotels-Hillbrook-Inn.h3082115.Hotel-Information) 21.7 km from Old Town Winchester 8.6/10 Excellent (671) "We had a wonderful time at Hillbrook. Loved the grounds, the cozy room, the spa massage was awesome!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nataliya CA $202 CA $261 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Martinsburg-Hotels-Hillbrook-Inn.h3082115.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/71000000/70930000/70921100/70921061/5447905f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/8897f4a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/3e194222.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) 4.1 km from Old Town Winchester 9.2/10 Wonderful (1402) "Clean room great helpful staff good breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Loretta CA $108 CA $118 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.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) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/120000/117800/117743/1687542a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom | Living area](https://images.trvl-media.com/lodging/1000000/120000/117800/117743/6b1b10e8.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) ### Spark by Hilton Winchester [](https://www.expedia.ca/Winchester-Hotels-Spark-By-Hilton-Winchester.h117743.Hotel-Information) 2 km from Old Town Winchester 9.0/10 Wonderful (1003) "The place is spotless, comfortable and quiet. Very convenient as well, right off of 81" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $105 CA $119 total includes taxes & fees Jan 25 - Jan 26, 2026 [](https://www.expedia.ca/Winchester-Hotels-Spark-By-Hilton-Winchester.h117743.Hotel-Information) ![Pillowtop beds, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/193cda05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/e6dc1dff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/164a5d2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/a3d383f7.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) 5.3 km from Old Town Winchester 9.4/10 Exceptional (788) "Great staff, very clean room with a good breakfast " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jim CA $146 CA $159 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/b1a55fc4.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) ![Egyptian cotton sheets, premium bedding, desk, blackout drapes](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/d78ffc9d.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) 2.9 km from Old Town Winchester 9.2/10 Wonderful (2236) "The place was clean, super friendly front desk staff, SO pet friendly with such a reasonable pet fee, and overall reasonable rate. Would 100% stay here again if I came back through this town. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jordyn CA $135 CA $147 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/5e25574f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/51a72e04.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/2000000/1660000/1652900/1652833/67cbe2e0.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/cbff06a1.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) 7.5 km from Old Town Winchester 8.8/10 Excellent (1002) "Have stayed here multiple times -always good" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $112 CA $122 total includes taxes & fees Jan 25 - Jan 26, 2026 [](https://www.expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.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) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/ad5604d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/9874bc44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/b96d495c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 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) 21.9 km from Old Town Winchester 9.0/10 Wonderful (1000) "Friendly staff, nice clean room, hotel restaurant was delicious. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dorothy CA $133 CA $147 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/737257e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/810f7f7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/afbe118c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/bb49c17d.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) 25 km from Old Town Winchester 9.0/10 Wonderful (1001) "Room was spotless, place was quiet and our welcome at the desk was perfect" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Merrill CA $156 CA $173 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.Hotel-Information) ![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652870/0a2d8398.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652870/3c75b4dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast meal](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652870/a5945e18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652870/61e9f06d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Candlewood Suites Winchester by IHG [](https://www.expedia.ca/Winchester-Hotels-Candlewood-Suites-Winchester.h1652870.Hotel-Information) 3.1 km from Old Town Winchester 8.8/10 Excellent (546) "The room was just the right temp, check in with my service dog was the most professional I’ve experienced! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shenandoah CA $107 CA $116 total includes taxes & fees Jan 16 - Jan 17, 2026 [](https://www.expedia.ca/Winchester-Hotels-Candlewood-Suites-Winchester.h1652870.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/w4000h2662x0y0-b556d792.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/fb0da257.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/27064e98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/b20fa3f2.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) 2.9 km from Old Town Winchester 9.0/10 Wonderful (802) "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 $127 CA $138 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Winchester-Hotels-Fairfield-Inn-Suites-By-Marriott-Winchester.h1066410.Hotel-Information) ![Courtyard](https://images.trvl-media.com/lodging/3000000/2770000/2762700/2762649/52d84062.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/3000000/2770000/2762700/2762649/6f99e56e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/3000000/2770000/2762700/2762649/a53cd216.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/3000000/2770000/2762700/2762649/acf14b95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Carriage Inn B&B [](https://www.expedia.ca/Martinsburg-Hotels-The-Carriage-Inn-BB.h2762649.Hotel-Information) 29.3 km from Old Town Winchester 9.6/10 Exceptional (439) "Excellent accommodations and breakfast. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William CA $210 CA $238 total includes taxes & fees Jan 8 - Jan 9, 2026 [](https://www.expedia.ca/Martinsburg-Hotels-The-Carriage-Inn-BB.h2762649.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) ![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) ![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) ### Holiday Inn Winchester Se-Historic Gateway by IHG [](https://www.expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information) 3.2 km from Old Town Winchester 9.0/10 Wonderful (1000) "Great room cozy bed fabulous restaurant great staff on property" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) joyce CA $107 CA $120 total includes taxes & fees Jan 25 - Jan 26, 2026 [](https://www.expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.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/cd85ec17.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) 4.3 km from Old Town Winchester 9.2/10 Wonderful (1001) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jaron CA $103 CA $113 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Winchester-Hotels-Quality-Inn.h172810.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/16000000/15950000/15945700/15945622/8c81eb2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/16000000/15950000/15945700/15945622/22bccc43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/16000000/15950000/15945700/15945622/a0a5a84e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Matisse at The Villa](https://images.trvl-media.com/lodging/16000000/15950000/15945700/15945622/957a1979.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### L'Auberge Provencale Inn & Restaurant [](https://www.expedia.ca/Winchester-Hotels-LAuberge-Provencale.h15945622.Hotel-Information) 14.1 km from Old Town Winchester 9.6/10 Exceptional (175) "This B&B has been by far the loveliest, friendliest, cleanest with staff so eager to please. The rural area was so peaceful and relaxing with views of black angus in the fields. Winchester close with quaint shops. The food at the Inn was excellent. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) DONNA CA $307 CA $339 total includes taxes & fees Jan 8 - Jan 9, 2026 [](https://www.expedia.ca/Winchester-Hotels-LAuberge-Provencale.h15945622.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/860000/855600/855557/5e0036d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room, 2 Double Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/860000/855600/855557/325feec2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/860000/855600/855557/4c979d71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super 8 by Wyndham Front Royal [](https://www.expedia.ca/Winchester-Hotels-Super-8-By-Wyndham-Front-Royal.h855557.Hotel-Information) 30.4 km from Old Town Winchester 7.6/10 Good (1001) "Good condition " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Phillip CA $85 CA $94 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Winchester-Hotels-Super-8-By-Wyndham-Front-Royal.h855557.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=2026-01-10&endDate=2026-01-11®ionId=6164092&adults=2&sort=RECOMMENDED&openPlayBack=true) ## Where to stay in Old Town Winchester Find the best Old Town Winchester areas and neighborhoods for the activities you enjoy most. - 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=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 While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Shenandoah Valley Discovery Museum. [See properties](https://www.expedia.ca/Hotel-Search?regionId=918789051029594112) ## Top Old Town Winchester Hotel Reviews ![Microtel Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/fab1f657_y.jpg) ### Microtel Inn & Suites by Wyndham Winchester 10/10 Excellent "My go to when visiting my parents. No frills, great price. Clean, decent coffee and breakfast (what you expect for the price) nice gym. Rooms are quiet. Bed comfortable and super easy parking. " [](https://expedia.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information) ![Comfort Inn & Suites Winchester](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/cf4c2663_y.jpg) ### Comfort Inn & Suites Winchester 10/10 Excellent "Very nice hotel for an overnight stop on way north. Right next to I-81 so we asked for (and received) a room on the parking lot side. Clean and comfortable room, but be sure to unfold the pillows before trying to sleep! Definitely recommend the nearby Bruster's Real Ice Cream for a treat, and the Sclafani's New York Bagels and Bread for breakfast!" [](https://expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb_y.jpg) ### La Quinta Inn & Suites by Wyndham Winchester 10/10 Excellent "The breakfast staff is helpful " [](https://expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![SpringHill Suites by Marriott Winchester](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/193cda05_y.jpg) ### SpringHill Suites by Marriott Winchester 10/10 Excellent "Great location, clean, safe, plenty of free parking and quiet, comfortable and spacious room." [](https://expedia.ca/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information) ![The George Washington Hotel, A Wyndham Grand Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5a07226c_y.jpg) ### The George Washington Hotel, A Wyndham Grand Hotel 10/10 Excellent "It would be nice if they had a business center that was actually a business center and not a storage room" [](https://expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![Holiday Inn Winchester Se-Historic Gateway by IHG](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/c68804b2_y.jpg) ### Holiday Inn Winchester Se-Historic Gateway by IHG 10/10 Excellent "Clean and quiet" [](https://expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information) ![TRU By Hilton Winchester](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/b9c1387b_y.jpg) ### TRU By Hilton Winchester 10/10 Excellent "Effortless check-in. Clean quiet room. Friendly staff" [](https://expedia.ca/Winchester-Hotels-TRU-By-Hilton-Winchester.h39493421.Hotel-Information) ![Rodeway Inn & Suites - Charles Town, WV](https://images.trvl-media.com/lodging/10000000/9870000/9868900/9868848/b6dd3662_y.jpg) ### Rodeway Inn & Suites - Charles Town, WV 10/10 Excellent "Clean room " [](https://expedia.ca/Martinsburg-Hotels-Rodeway-Inn-Suites.h9868848.Hotel-Information) ![Travelodge by Wyndham Winchester](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/9d44a9b1_y.jpg) ### Travelodge by Wyndham Winchester 10/10 Excellent "Clean" [](https://expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) ## Find out more about Old Town Winchester ### Top reasons to visit Old Town Winchester - **Historic Landmarks:** Discover fascinating historic sites through guided walking tours that showcase Old Town Winchester's rich heritage. - **Charming Downtown:** Stroll through picturesque streets filled with quaint shops and delightful eateries, embodying the town's warm hospitality. - **Outdoor Adventures:** Enjoy recreational areas and scenic lakes, blending culture and nature for a perfect family-friendly experience. - **Diverse Accommodations:** Choose from a range of hotels, including pet-friendly and LGBTQIA welcoming options, ensuring comfort for all travellers. - **Weekend Getaways:** Immerse yourself in the scenic beauty of the surrounding regions, perfect for an unforgettable escape. ### Find great hotels near Old Town Winchester Explore the charming hotel accommodations in Old Town Winchester, Virginia, where you can find a diverse range of options to suit every traveller's needs. Whether you're seeking pet-friendly lodgings, business-themed amenities, or LGBTQIA welcoming environments, this delightful area has something for everyone. Discover the best hotels, including Wyndham Winchester, and enjoy a memorable stay in a historic setting that beautifully blends modern comfort with timeless appeal. - **[Travelodge by Wyndham Winchester: ](https://www.expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information)** A welcoming and convenient motel experience awaits at Travelodge by Wyndham Winchester, situated 3.2km from Old Town Winchester. This property is ideal for pet lovers, offering a pet-friendly atmosphere that ensures your furry companions can join in on the adventure. With essential amenities and a commitment to comfort, guests appreciate the straightforward lodging combined with the convenience of nearby attractions. The pet policy allows for both pets and service animals, ensuring a hassle-free stay for all. - **[La Quinta Inn & Suites by Wyndham Winchester: ](https://www.expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information)** Emphasizing a business-friendly environment, La Quinta Inn & Suites by Wyndham Winchester is just 3.2km from Old Town Winchester and welcomes both corporate and leisure travellers. This hotel stands out with its dedicated business centre and versatile meeting rooms, making it perfect for business trips or conferences. Additionally, it's a proud ally of the LGBTQIA community, creating an inclusive atmosphere for all guests. With a pet-friendly policy and modern amenities, this hotel successfully blends work and play. - **Red Roof Inn Winchester, VA:** Family-oriented and pet-friendly, Red Roof Inn Winchester, VA is an excellent choice for those travelling with children, located 3.2km from Old Town Winchester. The hotel features child-friendly amenities such as complimentary cribs, ensuring a comfortable stay for families. Additionally, as a supporter of the LGBTQIA community, it fosters an inclusive environment for all guests. The property's pet policy caters to both dogs and cats, making it easy for families to bring their beloved pets along for the journey. ### Where to stay near Old Town Winchester Discover the charm of Old Town Winchester, where history meets hospitality. Stroll through the picturesque downtown, rich with historic attractions and family-friendly vibes. Enjoy Virginia's warm welcome as you explore quaint shops and delightful eateries. For a weekend getaway, immerse yourself in the scenic beauty of the surrounding regions, offering a perfect blend of urban and natural experiences. Old Town Winchester promises an unforgettable adventure for every traveller. - **[Winchester: ](https://www.expedia.ca/Winchester-Hotels.d6056879.Travel-Guide-Hotels)** Nestled in the heart of Virginia, Winchester is a vibrant city where Old Town Winchester serves as its historic nucleus. The city offers a year-round outdoor adventure experience, with scenic landscapes perfect for hiking and exploring. Popular activities include visiting nearby national parks and lakes, as well as enjoying skiing during the winter months. With a peak in visitor numbers during the summer and fall, Winchester is an excellent spot for those seeking both relaxation and adventure. - **[Winchester Historic District: ](https://www.expedia.ca/Winchester-Historic-District-Winchester-Hotels.0-n918789051029594112-0.Travel-Guide-Filter-Hotels)** Just 322m from Old Town Winchester, the Winchester Historic District is a charming neighborhood steeped in history. This area attracts families and outdoor enthusiasts alike, featuring golf courses and shopping centres. With its quaint parks and a welcoming visitor center, it's an ideal location to explore the unique blend of history and modern convenience. Expect a lively atmosphere, particularly during peak seasons in summer and autumn, making it a delightful stop for visitors looking for family-friendly activities. - **[College Park: ](https://www.expedia.ca/College-Park-Hotels.d553248635975870482.Travel-Guide-Hotels)** Located 3.2km from Old Town Winchester, College Park is a quaint village that perfectly complements your travel itinerary. Known for its outdoor experiences, this area offers excellent recreational opportunities and winter sports, including skiing. The proximity to national parks and a marina makes it attractive for nature lovers and adventure seekers. With a steady flow of visitors throughout the year, College Park provides a laid-back atmosphere to unwind and enjoy the scenic beauty of Virginia. ### Things to do in and around Old Town Winchester Old Town Winchester offers a delightful mix of outdoor and family-friendly activities. You can enjoy recreational areas and explore educational sites while shopping at the local centre. Don’t miss the chance to embark on guided walking tours through historic landmarks, providing a fascinating insight into the town's rich heritage. For a memorable experience, plan your trip around the charming streets of Old Town Winchester. **Shopping** In Old Town Winchester, you can find unique gifts at [Nalls Farm Market](https://www.expedia.ca/Nalls-Farm-Market-Hotels.0-l553248621532661846-0.Travel-Guide-Filter-Hotels), just 1.6km away. For a more extensive shopping experience, visit the Apple Valley Square Shopping Center and Eastgate Plaza Shopping Center, both offering a blend of local businesses and family-friendly vibes. **Recreation** [Jim Barnett Park](https://www.expedia.ca/Jim-Barnett-Park-Hotels.0-l6164028-0.Travel-Guide-Filter-Hotels) offers a tranquil environment for relaxation and leisurely strolls, only 1.4km from Old Town Winchester. For those seeking outdoor activities, [Rock Harbor Golf Course](https://www.expedia.ca/Rock-Harbor-Golf-Course-Hotels.0-l553248621561864838-0.Travel-Guide-Filter-Hotels), 3.2km away, provides a vibrant atmosphere for golf enthusiasts. [Appleland Sports Center](https://www.expedia.ca/Appleland-Sports-Center-Hotels.0-l553248621587477489-0.Travel-Guide-Filter-Hotels), 9.7km distant, focuses on wellness and rejuvenation. **Adventure** Experience the thrill of racing at [Summit Point Motorsports Park](https://www.expedia.ca/Summit-Point-Motorsports-Park-Hotels.0-l6164103-0.Travel-Guide-Filter-Hotels), located 17.7km from Old Town Winchester, where adrenaline meets speed. For a family-friendly outdoor adventure, visit [Watermelon Park Campground](https://www.expedia.ca/Watermelon-Park-Campground-Hotels.0-l553248621532661928-0.Travel-Guide-Filter-Hotels), 20.9km away, offering camping and nature activities. Don’t miss hiking the scenic [Tuckers Lane Trailhead](https://www.expedia.ca/Tuckers-Lane-Trailhead-Hotels.0-l553248633992585760-0.Travel-Guide-Filter-Hotels), 32.2km distant. **Nightlife** Experience the vibrant nightlife of Old Town Winchester at [Bright Box Theater](https://www.expedia.ca/Bright-Box-Theater-Hotels.0-l553248621561864843-0.Travel-Guide-Filter-Hotels), where culture and entertainment come alive. For a unique touch, visit the nearby [Morgan County Observatory](https://www.expedia.ca/Morgan-County-Observatory-Hotels.0-l553248621558141373-0.Travel-Guide-Filter-Hotels) for stargazing. Don’t miss the [Winchester Little Theater](https://www.expedia.ca/Winchester-Little-Theater-Hotels.0-l6164047-0.Travel-Guide-Filter-Hotels), perfect for a romantic evening filled with artistic charm. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Booking tips and Expedia advantages for Old Town Winchester To save money on your vacation to Old Town Winchester, consider visiting between January and March for lower accommodation rates. Tuesdays are typically the least expensive days to stay, while Saturdays are the priciest. Use Expedia to find deals by filtering for budget-friendly options and eco-certified hotels. Combining your hotel, flights, and activities into a package can also lead to significant savings. Take advantage of free local attractions and explore the town on foot to minimize transport costs. - **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay around Old Town 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 around Old Town Winchester is Tuesday. The most expensive day to stay around Old Town Winchester is Saturday. - **Find cheap hotels on Expedia:** Utilize Expedia's search tool to refine your preferences, such as your budget, desired location, and preferred hotel type. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly accommodations currently available. To find the best prices and deals, simply sort the price filter from lowest to highest. - **Consider bundling your trip:** You can save money by combining your hotel stay in Old Town Winchester with your flights and activities through an Expedia package. ### Find the best attractions in and around Old Town Winchester Old Town Winchester offers a delightful mix of outdoor adventures and family-friendly experiences, with attractions such as the historic downtown area and the scenic Winchester Historic District. Visitors can explore the charming historic houses and enjoy the nearby lakes, providing a perfect blend of culture and nature. Don't miss out on discovering the best attractions in Winchester, where history and outdoor fun come together beautifully for an unforgettable vacation. - **[Shenandoah University: ](https://www.expedia.ca/Shenandoah-University-Hotels.0-l6127311-0.Travel-Guide-Filter-Hotels)** This historic university, located 1.6km from Old Town Winchester, offers visitors a glimpse of vibrant campus life and beautiful architecture. Experience the cultural vibes through its various events and performances. - **[Museum of the Shenandoah Valley: ](https://www.expedia.ca/Museum-Of-The-Shenandoah-Valley-Hotels.0-l6127313-0.Travel-Guide-Filter-Hotels)** Situated 1.3km away, this art museum showcases regional art and history, providing a rich cultural experience. Explore its stunning galleries and beautiful gardens, perfect for a leisurely stroll. - **[Shenandoah Valley Discovery Museum: ](https://www.expedia.ca/Shenandoah-Valley-Discovery-Museum-Hotels.0-l553248621587527659-0.Travel-Guide-Filter-Hotels)** Located within Old Town Winchester, this children's museum is a delightful space for families. With interactive exhibits, it encourages learning through play, making it a wonderful destination for kids and parents alike. ### Best time to go to Old Town Winchester The best time to visit Old Town 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 Old Town Winchester For your visit to Old Town Winchester, you can fly into several nearby airports. 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, with nearby hotels like the 4-star [Hyatt Regency Dulles](https://www.expedia.ca/Herndon-Hotels-Hyatt-Regency-Dulles.h150.Hotel-Information), just 1.6km from the airport. Hagerstown Regional Airport ([HGR](https://www.expedia.ca/Hagerstown-Regional-Airport-Hotels.0-aHGR-0.Travel-Guide-Filter-Hotels)), located 69.2km away, offers options such as the 4-star Mercersburg Inn, 19.3km from the airport. The closest is Eastern West Virginia Regional Airport (MRB), situated 29.0km away, with accommodations like the 4-star [Hillbrook Inn](https://www.expedia.ca/Martinsburg-Hotels-Hillbrook-Inn.h3082115.Hotel-Information), 11.6kms from the airport. Each airport provides accessible transportation options to ensure a smooth journey to Old Town Winchester. ## Frequently asked questions ### What are the best hotels in Old Town Winchester that travellers recommend? ### What are the best family hotels in Old Town Winchester? ### What are the best spa hotels in Old Town Winchester? ### What are the best budget hotels in Old Town Winchester? ### Can I cancel my hotel reservation on Expedia? ### How can I save on a Old Town Winchester hotel booking with Expedia? ### How much is the nightly rate at a Old Town Winchester hotel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [4 Star Hotels in Stephens City ](https://www.expedia.ca/4Star-Stephens-City-Hotels.s40-0-d12076.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Winchester ](https://www.expedia.ca/4Star-Winchester-Hotels.s40-0-d6056879.Travel-Guide-Filter-Hotels) - [Hotels near Apple Blossom Mall ](https://www.expedia.ca/Apple-Blossom-Mall-Hotels.0-l6164018-0.Travel-Guide-Filter-Hotels) - 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