Title: Book the Best Winchester Hotels with FREE PARKING in 2026 | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d7876.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d7876.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d7876.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d7876.Destination-Travel-Guides) ![Thanks to my friend of mine who's recommended me to this spot easy hike short walk to get there ](https://images.trvl-media.com/place/7876/9403688e-dbbb-4255-9528-8bddb2ed4db3.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Nawa Aseen ![](https://images.trvl-media.com/place/7876/9403688e-dbbb-4255-9528-8bddb2ed4db3.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Winchester Hotels with Free Parking Tonight [Feb 24 - Feb 25](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-02-24&endDate=2026-02-25&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 25 - Feb 26](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-02-25&endDate=2026-02-26&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-02-27&endDate=2026-03-01&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-03-06&endDate=2026-03-08&adults=2&amenities=FREE_PARKING&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester hotels with parking ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/16300/16227/51af70a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/20000/16300/16227/eed31a13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/16300/16227/b6218bce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/16300/16227/93f7fc7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Winchester [](https://www.expedia.ca/Lexington-Hotels-Hampton-Inn-Winchester.h16227.Hotel-Information) Winchester 9.2/10 Wonderful (456 reviews) "Would stay there again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patricia CA $162 CA $179 total includes taxes & fees Feb 26 - Feb 27 [](https://www.expedia.ca/Lexington-Hotels-Hampton-Inn-Winchester.h16227.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/25000000/24370000/24362600/24362582/407ca96d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/25000000/24370000/24362600/24362582/04a3c81a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Accessible Bathtub (Accessible Tub)](https://images.trvl-media.com/lodging/25000000/24370000/24362600/24362582/60809f32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/25000000/24370000/24362600/24362582/fa38a8d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Lexington East - Winchester by IHG [](https://www.expedia.ca/Lexington-Hotels-Holiday-Inn-Express-Lexington-East-Winchester.h24362582.Hotel-Information) Winchester 9.2/10 Wonderful (546 reviews) "Clean room, great hot fresh breakfast " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bob CA $114 CA $126 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Lexington-Hotels-Holiday-Inn-Express-Lexington-East-Winchester.h24362582.Hotel-Information) ![Free daily full breakfast](https://images.trvl-media.com/lodging/1000000/20000/15300/15247/65f2c39d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/15300/15247/w5755h3835x5y5-d8ce41cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Double Beds, Non Smoking, Kitchenette](https://images.trvl-media.com/lodging/1000000/20000/15300/15247/w5755h3840x5y0-9326c0b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking, Kitchenette](https://images.trvl-media.com/lodging/1000000/20000/15300/15247/11f0b445.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Winchester Hotel [](https://www.expedia.ca/Lexington-Hotels-Best-Western-Winchester-Hotel.h15247.Hotel-Information) Winchester 8.4/10 Very good (1,000 reviews) "Clean room, friendly and fast check in service and had a great nights sleep " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cynthia CA $99 CA $109 total includes taxes & fees Feb 25 - Feb 26 [](https://www.expedia.ca/Lexington-Hotels-Best-Western-Winchester-Hotel.h15247.Hotel-Information) ![Suite, 1 King Bed, Hot Tub](https://images.trvl-media.com/lodging/109000000/108680000/108675700/108675613/d03fa6aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/109000000/108680000/108675700/108675613/489887ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/109000000/108680000/108675700/108675613/812dcf31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/109000000/108680000/108675700/108675613/d19dbf75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Value Stay [](https://www.expedia.ca/Lexington-Hotels-Value-Stay.h108675613.Hotel-Information) Winchester 7.8/10 Good (128 reviews) "Awesome rooms and service" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brandon CA $81 CA $89 total includes taxes & fees Mar 14 - Mar 15 [](https://www.expedia.ca/Lexington-Hotels-Value-Stay.h108675613.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/430000/422700/422677/023d86ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Queen Beds](https://images.trvl-media.com/lodging/1000000/430000/422700/422677/1f4d5f1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/430000/422700/422677/f8cf164e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/430000/422700/422677/f6477704.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Baymont by Wyndham Winchester [](https://www.expedia.ca/Lexington-Hotels-Baymont-By-Wyndham-Winchester.h422677.Hotel-Information) Winchester 7.2/10 Good (778 reviews) "Great place for a reasonable price! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Whitney CA $109 CA $120 total includes taxes & fees Mar 15 - Mar 16 [](https://www.expedia.ca/Lexington-Hotels-Baymont-By-Wyndham-Winchester.h422677.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/330000/327900/327866/df000477.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/330000/327900/327866/f0e4d2f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/330000/327900/327866/7d110afc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/1000000/330000/327900/327866/1ed60932.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn Winchester [](https://www.expedia.ca/Lexington-Hotels-Comfort-Inn.h327866.Hotel-Information) Winchester 7.0/10 Good (355 reviews) "This was the second time we’ve stopped here this year. It’s the perfect halfway respite between our home town and our destination. Very clean and comfortable. We will tag this as a regular stop on other trips. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Noelle CA $104 CA $114 total includes taxes & fees Mar 25 - Mar 26 [](https://www.expedia.ca/Lexington-Hotels-Comfort-Inn.h327866.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5900/5872/6bcbc7b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/5900/5872/b31a6feb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/5900/5872/08281b8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/5900/5872/ed324e5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Red Roof Inn Winchester - Lexington East [](https://www.expedia.ca/Lexington-Hotels-Red-Roof-Inn-Lexington-Winchester.h5872.Hotel-Information) Winchester 6.4/10 (591 reviews) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Walter CA $85 CA $94 total includes taxes & fees Mar 15 - Mar 16 [](https://www.expedia.ca/Lexington-Hotels-Red-Roof-Inn-Lexington-Winchester.h5872.Hotel-Information) ![Cabin, 2 Bedrooms, Kitchen | Living area](https://images.trvl-media.com/lodging/16000000/15440000/15437800/15437778/324d2660.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cabin, 2 Bedrooms, Kitchen | Living area](https://images.trvl-media.com/lodging/16000000/15440000/15437800/15437778/fa7fc3aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cabin, 2 Bedrooms, Kitchen | Terrace/patio](https://images.trvl-media.com/lodging/16000000/15440000/15437800/15437778/278782c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cabin, 2 Bedrooms, Kitchen | In-room dining](https://images.trvl-media.com/lodging/16000000/15440000/15437800/15437778/c7bf72a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Natural Bridge State Resort Park [](https://www.expedia.ca/Slade-Hotels-Natural-Bridge-State-Resort-Park.h15437778.Hotel-Information) Slade 8.6/10 Excellent (1,806 reviews) "Great setting and very convenient to everything. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) WILLIAM [](https://www.expedia.ca/Slade-Hotels-Natural-Bridge-State-Resort-Park.h15437778.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/12000000/11860000/11855100/11855099/800aa1cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Double Beds | Porch](https://images.trvl-media.com/lodging/12000000/11860000/11855100/11855099/92f44bf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Double Beds](https://images.trvl-media.com/lodging/12000000/11860000/11855100/11855099/08288a3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/12000000/11860000/11855100/11855099/65bd90f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Black Bear Lodge Motel [](https://www.expedia.ca/Slade-Hotels-Black-Bear-Lodge-Motel.h11855099.Hotel-Information) Slade 8.0/10 Very good (639 reviews) "Really great place to stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Barbara CA $120 CA $133 total includes taxes & fees Mar 11 - Mar 12 [](https://www.expedia.ca/Slade-Hotels-Black-Bear-Lodge-Motel.h11855099.Hotel-Information) ![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/50000/42500/42455/8d6292d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/42500/42455/81b02df3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/42500/42455/63967dd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/50000/42500/42455/74e92478.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Mount Sterling [](https://www.expedia.ca/Mount-Sterling-Hotels-Comfort-Inn-And-Suites.h42455.Hotel-Information) Mount Sterling 7.8/10 Good (722 reviews) "We stay here anytime we are in town " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Donn CA $106 CA $117 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Mount-Sterling-Hotels-Comfort-Inn-And-Suites.h42455.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=2026-03-10&endDate=2026-03-11®ionId=7876&adults=2&amenities=FREE_PARKING&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AFFINITY_SPRING_PROMO_7876) ## Top Winchester Hotel Reviews ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [Hotels near Applebee s Park ](https://www.expedia.ca/Applebee-S-Park-Hotels.0-l553248621557921127-0.Travel-Guide-Filter-Hotels) - [Motels in Camargo ](https://www.expedia.ca/Camargo-Motels.d553248634998850038-aaMotels.Travel-Guide-Accommodation) - [Chevy Chase Hotels ](https://www.expedia.ca/Chevy-Chase-Lexington-Hotels.0-n553248635976481361-0.Travel-Guide-Filter-Hotels) - [Hotels near Claiborne Farm ](https://www.expedia.ca/Claiborne-Farm-Hotels.0-l553248621559866398-0.Travel-Guide-Filter-Hotels) - [Cabin Rentals in Clay City ](https://www.expedia.ca/Clay-City-Cabins.d3000438412-aaCabins.Travel-Guide-Accommodation) - [Guest Houses in Clay City ](https://www.expedia.ca/Clay-City-Guest-Houses.d3000438412-aaGuestHouses.Travel-Guide-Accommodation) - [Clay City Hotels ](https://www.expedia.ca/Clay-City-Hotels.d3000438412.Travel-Guide-Hotels) - 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