Title: Book the Best Old Town Winchester Hotels with FREE PARKING in 2025 | Expedia.ca [Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d6056879.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.ca/Cheap-Flights-To-Winchester.d6056879.Travel-Guide-Flights)[Things to do in Winchester](https://expedia.ca/Things-To-Do-In-Winchester.d6056879.Travel-Guide-Activities)[Old Town Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Old-Town-Winchester.d6164092.Car-Rental-Guide)[Old Town Winchester Vacations](https://expedia.ca/Old-Town-Winchester.d6164092.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/720fb116634761161ecda43d4ca150e7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with Free Parking in Old Town Winchester, VA from CA $102 ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Old Town Winchester Hotels with Free Parking Tonight [Oct 25 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6164092&startDate=2025-10-25&endDate=2025-10-26&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 26 - Oct 27](https://www.expedia.ca/Hotel-Search?regionId=6164092&startDate=2025-10-26&endDate=2025-10-27&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6164092&startDate=2025-10-31&endDate=2025-11-02&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6164092&startDate=2025-11-07&endDate=2025-11-09&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Old Town Winchester Hotels with Free Parking ![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) ![1 bedroom, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/6a37f73c.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) ### Comfort Inn & Suites Winchester Winchester 9.4/10 Exceptional (1044) "The breakfast was good and a quiet place to stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lawrence CA $142 CA $154 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.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) ![Lobby](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/41cd029b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/ffce1877.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Winchester Winchester 9.2/10 Wonderful (2183) "Great hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $144 CA $156 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.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) ![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/e8922549.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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 Winchester 9.2/10 Wonderful (1344) "Great place with very cute rooms!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) kristy CA $109 CA $118 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information) ![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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/d6b37fa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/a8e7d0d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5707228d.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 (1007) "Very nice hotel " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul CA $177 CA $201 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.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) ![Dining](https://images.trvl-media.com/lodging/11000000/10630000/10620700/10620696/9b09e95c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Laundry room](https://images.trvl-media.com/lodging/11000000/10630000/10620700/10620696/85c667fa.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 Charles Town 8.0/10 Very good (1008) "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 Nov 2 - Nov 3 [](https://www.expedia.ca/Martinsburg-Hotels-Days-Inn-By-Wyndham-Charles-TownHarpers-Ferry.h10620696.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) ![Interior](https://images.trvl-media.com/lodging/4000000/3090000/3082200/3082115/f8c19c35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/4000000/3090000/3082200/3082115/9aa4d92c.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) ### Hillbrook Inn Charles Town 8.6/10 Excellent (670) "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 $236 CA $300 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Martinsburg-Hotels-Hillbrook-Inn.h3082115.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) ![Lobby](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/76fedaf8.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) ![Reception](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/bf8dce02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### TRU By Hilton Winchester Winchester 9.0/10 Wonderful (731) "Clean room easy check in/out" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Edward CA $126 CA $137 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Winchester-Hotels-TRU-By-Hilton-Winchester.h39493421.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) ![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) ![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) ![Lobby](https://images.trvl-media.com/lodging/10000000/9870000/9868900/9868848/56958e5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rodeway Inn & Suites - Charles Town, WV Charles Town 8.6/10 Excellent (1019) "It is a very good place to stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kimberly CA $90 CA $102 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Martinsburg-Hotels-Rodeway-Inn-Suites.h9868848.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) ![The Mary Rutherford Room](https://images.trvl-media.com/lodging/3000000/2770000/2762700/2762649/fead0911.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) ![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) ### The Carriage Inn B&B Charles Town 9.6/10 Exceptional (432) "Excellent accommodations and breakfast. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William CA $222 CA $251 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Martinsburg-Hotels-The-Carriage-Inn-BB.h2762649.Hotel-Information) ![1 bedroom, pillowtop beds, desk, laptop workspace](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/193cda05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/57a6dfe3.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) ![Lobby](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/164a5d2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SpringHill Suites by Marriott Winchester Winchester 9.6/10 Exceptional (748) "Nice place, very quiet, comfie beds, and great staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leslie CA $156 CA $170 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.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=2025-11-08&endDate=2025-11-09®ionId=6164092&adults=2&amenities=FREE_PARKING&sort=RECOMMENDED&openPlayBack=true) ## Top Old Town Winchester Hotel Reviews ![Hampton Inn Front Royal](//images.trvl-media.com/lodging/1000000/900000/892600/892585/737257e0_y.jpg) ### Hampton Inn Front Royal 10/10 Excellent "We thoroughly enjoyed all aspects of our stay, and look forward to the next time." [](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.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 "Our room was great and fresh. Dinner at the hotel restaurant was delicious and the staff was friendly and welcoming. " [](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 "Good" [](https://expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.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 for the value!! " [](https://expedia.ca/Martinsburg-Hotels-Rodeway-Inn-Suites.h9868848.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 "New contemporary hotel; comfortable bed and nicely decorated room. Good location to restaurants and the highway. Nice staff and good breakfast (standard food items). Only complaint is that need a few more parking spaces. " [](https://expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![Travelodge by Wyndham Winchester](//images.trvl-media.com/lodging/1000000/10000/9600/9600/28616e5b_y.jpg) ### Travelodge by Wyndham Winchester 10/10 Excellent "Clean room. Good breakfast" [](https://expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) ![Hampton Inn Winchester-University/Mall Area](//images.trvl-media.com/lodging/1000000/20000/20000/19971/17b0fc68_y.jpg) ### Hampton Inn Winchester-University/Mall Area 10/10 Excellent "Parking area felt very safe. Fruit available for breakfast. " [](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.Hotel-Information) ![Ramada by Wyndham Strasburg/Shenandoah Valley](//images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/08da8378_y.jpg) ### Ramada by Wyndham Strasburg/Shenandoah Valley 10/10 Excellent "Staff was friendly. Room was clean. Restaurant attached to hotel was tasty. Thumbs up." [](https://expedia.ca/Winchester-Hotels-Ramada-By-Wyndham-Strasburg.h1246311.Hotel-Information) ![Courtyard by Marriott Winchester](//images.trvl-media.com/lodging/2000000/1500000/1497900/1497898/8f242b36_y.jpg) ### Courtyard by Marriott Winchester 10/10 Excellent "Clean well kept hotel. Staff was very friendly. The location was perfect for the event we were attending. Have stayed here before and will again. 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