Title: 10 Best Hotels in Old Town Winchester, Winchester for 2025 | Expedia.ca [Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d6056879.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.ca/Cheap-Flights-To-Winchester.d6056879.Travel-Guide-Flights)[Things to do in Winchester](https://expedia.ca/Things-To-Do-In-Winchester.d6056879.Travel-Guide-Activities)[Old Town Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Old-Town-Winchester.d6164092.Car-Rental-Guide)[Old Town Winchester Vacations](https://expedia.ca/Old-Town-Winchester.d6164092.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Hotels in Old Town Winchester, Winchester ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Go beyond your typical stay in Old Town Winchester Family friendly [](https://www.expedia.ca/Hotel-Search?destination=Old+Town+Winchester%2C+Winchester%2C+Virginia%2C+United+States+of+America®ionId=6164092&latLong=39.18421%2C-78.16561&adults=2&startDate=2025-10-11&d1=2025-10-11&endDate=2025-10-13&d2=2025-10-13&travelerType=family_friendly) Apart­ment [](https://www.expedia.ca/Hotel-Search?destination=Old+Town+Winchester%2C+Winchester%2C+Virginia%2C+United+States+of+America®ionId=6164092&latLong=39.18421%2C-78.16561&adults=2&startDate=2025-10-11&d1=2025-10-11&endDate=2025-10-13&d2=2025-10-13&lodging=APARTMENT) Pool [](https://www.expedia.ca/Hotel-Search?destination=Old+Town+Winchester%2C+Winchester%2C+Virginia%2C+United+States+of+America®ionId=6164092&latLong=39.18421%2C-78.16561&adults=2&startDate=2025-10-11&d1=2025-10-11&endDate=2025-10-13&d2=2025-10-13&amenities=POOL) Pet friendly [](https://www.expedia.ca/Hotel-Search?destination=Old+Town+Winchester%2C+Winchester%2C+Virginia%2C+United+States+of+America®ionId=6164092&latLong=39.18421%2C-78.16561&adults=2&startDate=2025-10-11&d1=2025-10-11&endDate=2025-10-13&d2=2025-10-13&amenities=PETS) ## Check prices for these dates Tonight [Sep 27 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=6164092&startDate=2025-09-27&endDate=2025-09-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 28 - Sep 29](https://www.expedia.ca/Hotel-Search?regionId=6164092&startDate=2025-09-28&endDate=2025-09-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=6164092&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6164092&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Recommended Price (low to high) Distance Star rating ## Old Town Winchester hotels and places to stay ![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) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/bff9ad76.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 Old Town Winchester 9.4/10 Exceptional (1015) "Perfect location to visit for business or pleasure!" CA $176 CA $200 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.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) ![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) ![Lobby](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/41cd029b.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) ### La Quinta Inn & Suites by Wyndham Winchester 2.9 km from Old Town Winchester 9.2/10 Wonderful (2167) "Would stay again if in the area. " CA $151 CA $164 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.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 3.1 km from Old Town Winchester 8.8/10 Excellent (512) "The suites we're clean and spacious. The perfect stay for a family weekend!" CA $130 CA $141 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Winchester-Hotels-Candlewood-Suites-Winchester.h1652870.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) ![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) ![Lobby sitting area](https://images.trvl-media.com/lodging/77000000/76880000/76876900/76876848/a19abecc.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) ### The Inn at Charles Town - Hollywood Casino 30 km from Old Town Winchester 8.6/10 Excellent (493) "It is convenient to the casino and racetrack. The continental breakfast was average at best. For a tremendous breakfast try the Charlestown Family Diner across the street from this property." CA $141 CA $172 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Charles-Town-Hotels-The-Inn-At-Charles-Town.h76876848.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) ![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) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/b6f40366.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Winchester Se-Historic Gateway by IHG 3.2 km from Old Town Winchester 9.0/10 Wonderful (1014) "Great hotel! " CA $123 CA $138 total includes taxes & fees Oct 26 - Oct 27 [](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) ![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) ![Lobby](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/c7da6581.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Winchester 4.3 km from Old Town Winchester 9.2/10 Wonderful (1014) "Dog friendly, quiet and clean. " CA $117 CA $128 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Winchester-Hotels-Quality-Inn.h172810.Hotel-Information) ![Elevator](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/08da8378.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/9ef74ac2.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/2000000/1250000/1246400/1246311/e47a228e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/9fcf0199.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ramada by Wyndham Strasburg/Shenandoah Valley 25.8 km from Old Town Winchester 8.2/10 Very good (1001) "Room was very clean and comfortable. Breakfast was basic but better than most I've been to recently. Very satisfied with the stay." CA $105 CA $117 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Winchester-Hotels-Ramada-By-Wyndham-Strasburg.h1246311.Hotel-Information) ![Premium bedding, pillowtop beds, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/73000000/72030000/72023600/72023562/fc21f98c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/73000000/72030000/72023600/72023562/w3000h1998x0y0-156eb7d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/73000000/72030000/72023600/72023562/5ec973d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free continental breakfast](https://images.trvl-media.com/lodging/73000000/72030000/72023600/72023562/c6b45b54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Travelodge By Wyndham Charles Town/Harpers Ferry 29.5 km from Old Town Winchester 7.0/10 Good (241) "Wasn’t the cleanest but it’s good for a quick stop" CA $88 CA $99 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Charles-Town-Hotels-Travelodge-By-Wyndham-Charles-TownHarpers-Ferry.h72023562.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) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/f063e2e9.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) ![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) ### Fairfield Inn & Suites by Marriott Winchester 2.9 km from Old Town Winchester 9.0/10 Wonderful (768) "This was a very clean well run hotel and the staff was friendly and accomodating. Would definitely stay here again." CA $135 CA $147 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Winchester-Hotels-Fairfield-Inn-Suites-By-Marriott-Winchester.h1066410.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1330000/1327400/1327336/73114153.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1330000/1327400/1327336/368a0b33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Non Smoking (Drinks & Snacks)](https://images.trvl-media.com/lodging/2000000/1330000/1327400/1327336/a5bd4bfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/2000000/1330000/1327400/1327336/02fadc90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Martinsburg South-Inwood 22.3 km from Old Town Winchester 9.2/10 Wonderful (619) "The property was very clean and the breakfast was excellent." CA $141 CA $158 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Martinsburg-Hotels-Hampton-Inn-Martinsburg-South-Inwood.h1327336.Hotel-Information) ![In-room safe, desk, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/28616e5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/d7931645.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/w3000h1997x0y0-2ca33d0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room, 2 Double Beds, Smoking](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/65ba6c12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Travelodge by Wyndham Winchester 2.9 km from Old Town Winchester 8.4/10 Very good (1098) "My favorite hotel in VA, always stay there when visiting friends and family. " CA $98 CA $106 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2170000/2169500/2169428/689131eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/3000000/2170000/2169500/2169428/a7fe3c2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2170000/2169500/2169428/a948cd9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2170000/2169500/2169428/037b096c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Winchester 2.1 km from Old Town Winchester 8.8/10 Excellent (493) "A great stop for our family of four on a long drive home." CA $153 CA $173 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Winchester-Hotels-Hilton-Garden-Inn-Winchester.h2169428.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/1000000/20000/10600/10535/071235b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/10600/10535/a2451115.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/20000/10600/10535/ff7a3bf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/10600/10535/c5b2135d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Baymont by Wyndham Front Royal Near Shenandoah National Park 29.8 km from Old Town Winchester 6.4/10 (882) "nice for a great stay!!" CA $78 CA $87 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Winchester-Hotels-Baymont-By-Wyndham-Front-Royal-Near-Shenandoah-National-Park.h10535.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/17b0fc68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout drapes, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/a888dfb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/800932de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/16920465.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Winchester-University/Mall Area 2.1 km from Old Town Winchester 9.0/10 Wonderful (1013) "Price, Clean!,great breakfast, attention to details and nice room, loved it!" CA $124 CA $140 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.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) ![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) ![Standard Room, 1 King Bed, Smoking](https://images.trvl-media.com/lodging/10000000/9870000/9868900/9868848/71615746.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rodeway Inn & Suites - Charles Town, WV 29.7 km from Old Town Winchester 8.6/10 Excellent (1024) "Shops near by Harper’s ferry " CA $94 CA $106 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Martinsburg-Hotels-Rodeway-Inn-Suites.h9868848.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1500000/1497900/1497898/8f242b36.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/cab9baeb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1500000/1497900/1497898/1b2ad59b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Winchester 3.1 km from Old Town Winchester 8.8/10 Excellent (881) " Nice hotel" CA $149 CA $162 total includes taxes & fees Oct 5 - Oct 6 [](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) ![Room, 2 Queen Beds](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/c99442ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/daf3dfdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/76fedaf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### TRU By Hilton Winchester 4.4 km from Old Town Winchester 9.0/10 Wonderful (705) "Clean decent size room, easy parking, not too far from highway, lots of traffic around but the room was very quiet" CA $139 CA $151 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Winchester-Hotels-TRU-By-Hilton-Winchester.h39493421.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/1000000/120000/117800/117743/6b1b10e8.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) ![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 2 km from Old Town Winchester 9.0/10 Wonderful (1005) "Front desk person was very helpful" CA $128 CA $145 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Winchester-Hotels-Spark-By-Hilton-Winchester.h117743.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/40000/34400/34394/4d102079.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/40000/34400/34394/71be8e87.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/db46282e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Winchester South-Stephens City by IHG 12.4 km from Old Town Winchester 8.2/10 Very good (772) "Great stay!" CA $130 CA $141 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Winchester-Hotels-Holiday-Inn-Express-Winchester-South-Stephens-City.h34394.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) ![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 21.9 km from Old Town Winchester 9.0/10 Wonderful (1008) "Nice property and great location. " CA $165 CA $186 total includes taxes & fees Oct 26 - Oct 27 [](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=2025-10-11&endDate=2025-10-12®ionId=6164092&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FOld-Town-Winchester-Winchester-Hotels.0-n6164092-0.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FOld-Town-Winchester-Winchester-Hotels.0-n6164092-0.Travel-Guide-Filter-Hotels) ## 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:ctdnFtsd%7CM%7DI%7DECA%5BQeAo%40iAs%40L_%40DB%5E%7BAFDDSDSf%40NDUHBR%7D%40RFLo%40o%40Wc%40USGHeBDuADw%40HaCjDM%3FETkCHcAeAG%7B%40Ew%40El%40mFFMFIFGJGHAJ%3FtA%5CRB%5CuC%5BGVwB_CaBaGgEiNmJ%3F%5B%7C%40iFi%40o%40Z%7BBDCHg%40Hq%40F_%40BSBS%60%40LFi%40F_%40Da%40Fa%40XHR%5BHk%40Hg%40OGHe%40%3FGPgALy%40p%40R%3F_%40L%7B%40%5EJRAd%40NDUBUBONDNDNDNDNDNDNDJBVHPFNBLBn%40PZYb%40J%40%40RFTcBbAXLDJc%40%5CuBDUN%7D%40MGAAc%40KDUW%40SAK%3Fa%40G_%40KHa%40VcBFQLy%40l%40PRHPFRFCP%7EAd%40BSxA%60%40ERRFVFN%3FNDEZJBND%40%40AFJDbAXGXEXALp%40RnG%7DAf%40KCLk%40zDaFwAC%60%40Mx%40Kt%40ZJa%40nCd%40NbAX%5CmCTDRFhAXVmB%7C%40VFc%40v%40oFJK%60%40%3FVB%5CDb%40JnCx%40nDbAF_%40RsAT%7DA%7EBn%40hClAh%40NlBv%40Kn%40_%40bCxA%60%40c%40lDYfBRj%40Kl%40E%5ELDEZ%3F%3FCXNDRFA%40XH%5C%3Fb%40LTFRFRFXHVRf%40NCTCLALCLCRId%40%5B%5EE%5CG%5CXJPDCPALCJCLADA%3FGASIMCGd%40Ib%40Kr%40O%60%40U%7EAHBTFRFCPERE%5CAJERYIG%60%40Ij%40%5DXM%7C%40ZJG%5ETHABKp%40z%40VBn%40JD%60%40JZLBM%60%40J%5EJQnAIb%40WlB%7B%40WC%3FECCNy%40Ui%40f%40%5BK%3FAOGMGA%3F%7B%40YEe%40MGq%40Q%3FABKc%40Ki%40O%5BAg%40O_%40KYIYIc%40R%5DKg%40QAJw%40WQw%40q%40Sg%40Oc%40Mc%40Pe%40O%3FDuAa%40%5D%40UIQGFe%40OE%3FBGCICm%40OCAk%40Oi%40%60%40QG%40CSEi%40ODWMCU%7CAGFM%60%40QnAKECJOp%40RFKl%40If%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%5EsEzY&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=fZ5k4VxrY6HuuI7umpgpSp91zQs=) ### Winchester Historic District While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Winchester Little Theater. [See properties](https://www.expedia.ca/Hotel-Search?regionId=918789051029594112) ## Top Old Town Winchester Hotel Reviews ![Courtyard by Marriott Winchester](//images.trvl-media.com/lodging/2000000/1500000/1497900/1497898/8f242b36_y.jpg) ### Courtyard by Marriott Winchester 10/10 Excellent "Very friendly staff and clean facilities." [](https://expedia.ca/Winchester-Hotels-Courtyard-By-Marriott-Winchester.h1497898.Hotel-Information) ![Rodeway Inn & Suites - Charles Town, WV](//images.trvl-media.com/lodging/10000000/9870000/9868900/9868848/b6dd3662_y.jpg) ### Rodeway Inn & Suites - Charles Town, WV 10/10 Excellent "Great stay!" [](https://expedia.ca/Martinsburg-Hotels-Rodeway-Inn-Suites.h9868848.Hotel-Information) ![DoubleTree by Hilton Front Royal Blue Ridge Shadows](//images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/204cbf3a_y.jpg) ### DoubleTree by Hilton Front Royal Blue Ridge Shadows 10/10 Excellent "This is a convenient place to stop off if you've been visiting the Blue Ridge Mountains and Shenandoah National Park. It's out of town slightly, so you would have to drive if you were looking for somewhere else to eat. The restaurant was an unremarkable diner with average food - definitely not a destination - but the staff were friendly. " [](https://expedia.ca/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.Hotel-Information) ![Holiday Inn Winchester Se-Historic Gateway by IHG](//images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/c68804b2_y.jpg) ### Holiday Inn Winchester Se-Historic Gateway by IHG 10/10 Excellent "Everything was great except I feel the website should have updated that the restaurant was closed. The beds were amazing and had some issues connecting to the WiFi, but overall a good stay. " [](https://expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information) ![The George Washington Hotel, A Wyndham Grand Hotel](//images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5a07226c_y.jpg) ### The George Washington Hotel, A Wyndham Grand Hotel 10/10 Excellent "The beauty of the property to begin with. Old world charm but modernized without detracting from the original character. The grand mailbox, each floor having a mailbox which directly connects with and is fed by gravity to the “grand” collection box on the ground floor! Beautiful! The basement pool is a spectacle to behold! The beauty along with the perfect water temperature provided a perfect ending to our evening!" [](https://expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Winchester](//images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb_y.jpg) ### La Quinta Inn & Suites by Wyndham Winchester 10/10 Excellent "This location has to be one of the best hotels I have ever stayed in. Very very clean, friendly people and a super good breakfast. They actually had someone restocking the breakfast bar. Pet friendly too. Very convenient access on and off the highway at a very reasonable rate for the night. " [](https://expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![Comfort Inn & Suites Winchester](//images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/cf4c2663_y.jpg) ### Comfort Inn & Suites Winchester 10/10 Excellent "It’s my happy place when I’m traveling to and from NY from NC" [](https://expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information) ![Hampton Inn Front Royal](//images.trvl-media.com/lodging/1000000/900000/892600/892585/75c26333_y.jpg) ### Hampton Inn Front Royal 10/10 Excellent "Met our needs for a convenient 1 night lay over. Every thing was fine, room clean & neat. Staff was friendly and offered all the help we needed. " [](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.Hotel-Information) ![Country Inn & Suites by Radisson, Winchester, VA](//images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/d0690cde_y.jpg) ### Country Inn & Suites by Radisson, Winchester, VA 10/10 Excellent "Wifi wasn't great" [](https://expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.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? > [The George Washington Hotel, A Wyndham Grand Hotel](https://www.expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information), is a highly praised destination in Old Town Winchester, boasting a great rating of 9.4. This Georgian-style property offers a luxurious retreat with a full-service spa, superb for those looking to unwind after a day of adventure. Guests rave about the onsite massage services and the option for in-room pampering, ensuring a relaxing stay. ### What are the best family hotels in Old Town Winchester? > [The George Washington Hotel, A Wyndham Grand Hotel](https://www.expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information), stands out as an exceptional choice for families visiting Old Town Winchester, boasting an impressive traveller review score of 9.4. This hotel not only offers connecting rooms, making it convenient for families to stay close together, but also provides free cribs for little ones, ensuring a comfortable stay for guests of all ages. ### What are the best spa hotels in Old Town Winchester? > For a rejuvenating escape, [The George Washington Hotel, A Wyndham Grand Hotel](https://www.expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) is a great choice in Old Town Winchester, boasting an impressive customer review rating of 9.4. This historic hotel features a full-service spa where guests can indulge in a range of treatments, including in-room massages, ensuring a personalized and relaxing experience. ### What are the best budget hotels in Old Town Winchester? > [The George Washington Hotel, A Wyndham Grand Hotel](https://www.expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information), is a fantastic option for travellers seeking comfort and convenience in Old Town Winchester. With a stellar review rating of 9.4, this hotel effortlessly combines modern amenities with a touch of historic charm. ### Can I cancel my hotel reservation on Expedia? > You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Old Town Winchester. ### How can I save on a Old Town Winchester hotel booking with Expedia? > Members always get our best prices. Find our best Old Town Winchester hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings. ### How much is the nightly rate at a Old Town Winchester hotel? > Hotel prices in Old Town Winchester often vary, but you can find a great deal on Expedia. Different factors affect nightly hotel rates, such as the time of year or the days of the week you want to book. 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[Hotels in Winchester Historic District](https://expedia.ca/Winchester-Historic-District-Winchester-Hotels.0-n918789051029594112-0.Travel-Guide-Filter-Hotels) ### Hotels near popular Winchester Attractions - [Hotels near Shenandoah Valley Discovery Museum](https://expedia.ca/Shenandoah-Valley-Discovery-Museum-Hotels.0-l553248621587527659-0.Travel-Guide-Filter-Hotels) - [Hotels near Bright Box Theater](https://expedia.ca/Bright-Box-Theater-Hotels.0-l553248621561864843-0.Travel-Guide-Filter-Hotels) - [Hotels near Handley Regional Library](https://expedia.ca/Handley-Regional-Library-Hotels.0-l6164024-0.Travel-Guide-Filter-Hotels) - [Hotels near George Washington's Office](https://expedia.ca/George-Washingtons-Office-Hotels.0-l6164042-0.Travel-Guide-Filter-Hotels) - [Hotels near Old Court House Civil War Museum](https://expedia.ca/Old-Court-House-Civil-War-Museum-Hotels.0-l553248621532661844-0.Travel-Guide-Filter-Hotels) - [Hotels near Hollywood Casino at Charles Town Races](https://expedia.ca/Hollywood-Casino-At-Charles-Town-Races-Hotels.0-l553248621532661960-0.Travel-Guide-Filter-Hotels) - [Hotels near Summit Point Motorsports Park](https://expedia.ca/Summit-Point-Motorsports-Park-Hotels.0-l6164103-0.Travel-Guide-Filter-Hotels) - [Hotels near Shenandoah River](https://expedia.ca/Shenandoah-River-Hotels.0-l681974697590321152-0.Travel-Guide-Filter-Hotels) - [Hotels near Winchester Medical Center](https://expedia.ca/Winchester-Medical-Center-Hotels.0-l6164057-0.Travel-Guide-Filter-Hotels) - [Hotels near Shenandoah University](https://expedia.ca/Shenandoah-University-Hotels.0-l6127311-0.Travel-Guide-Filter-Hotels) ### More Hotel Options in Old Town Winchester - [Beach Hotel in Old Town Winchester](https://expedia.ca/Old-Town-Winchester-Winchester-Hotels-Beach-Hotel.0-n6164092-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Old Town Winchester](https://expedia.ca/Old-Town-Winchester-Winchester-Hotels-Boutique-Hotel.0-n6164092-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Business Hotels in Old Town Winchester](https://expedia.ca/Old-Town-Winchester-Winchester-Hotels-Business-Hotel.0-n6164092-0-tBusinessHotel.Travel-Guide-Filter-Hotels) - 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[Motel 6 Hotels](https://expedia.ca/Old-Town-Winchester-Winchester-Hotels-Motel-6.0-n6164092-0--bMotel6.Travel-Guide-Filter-Hotels) ### Explore more hotels - [Days Inn by Wyndham Charles Town/Harpers Ferry](https://expedia.ca/Martinsburg-Hotels-Days-Inn-By-Wyndham-Charles-TownHarpers-Ferry.h10620696.Hotel-Information) - [DoubleTree by Hilton Front Royal Blue Ridge Shadows](https://expedia.ca/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.Hotel-Information) - [Hampton Inn Front Royal](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.Hotel-Information) - [Travelodge by Wyndham Winchester](https://expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) - [Spark by Hilton Winchester](https://expedia.ca/Winchester-Hotels-Spark-By-Hilton-Winchester.h117743.Hotel-Information) - [Quality Inn Winchester](https://expedia.ca/Winchester-Hotels-Quality-Inn.h172810.Hotel-Information) - [Rodeway Inn & Suites - Charles Town, WV](https://expedia.ca/Martinsburg-Hotels-Rodeway-Inn-Suites.h9868848.Hotel-Information) - [The Inn at Charles Town - Hollywood Casino](https://expedia.ca/Charles-Town-Hotels-The-Inn-At-Charles-Town.h76876848.Hotel-Information) - [Baymont by Wyndham Front Royal Near Shenandoah National Park](https://expedia.ca/Winchester-Hotels-Baymont-By-Wyndham-Front-Royal-Near-Shenandoah-National-Park.h10535.Hotel-Information) - [Super 8 by Wyndham Front Royal](https://expedia.ca/Winchester-Hotels-Super-8-By-Wyndham-Front-Royal.h855557.Hotel-Information) - [TRU By Hilton Winchester](https://expedia.ca/Winchester-Hotels-TRU-By-Hilton-Winchester.h39493421.Hotel-Information) - [Fairfield Inn & Suites by Marriott Winchester](https://expedia.ca/Winchester-Hotels-Fairfield-Inn-Suites-By-Marriott-Winchester.h1066410.Hotel-Information) [See a list of all hotels in Winchester](https://expedia.ca/All-Winchester-Hotels.d6056879.Travel-Guide-City-All-Hotels) ### More ways to book - [Book Hotels in Old Town Winchester on Expedia.com](https://www.expedia.com/Old-Town-Winchester-Winchester-Hotels.0-n6164092-0.Travel-Guide-Filter-Hotels) ### Expedia's Latest Trends Hotels - 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