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 ![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) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/15300/15247/w5755h3835x5y5-d8ce41cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/20000/15300/15247/c153c2fa.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/16300/16227/51af70a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Accessible, Non Smoking](https://images.trvl-media.com/lodging/1000000/20000/16300/16227/83fc2e38.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) ![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) ![Reception](https://images.trvl-media.com/lodging/109000000/108680000/108675700/108675613/812dcf31.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/109000000/108680000/108675700/108675613/33a8f318.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 13 - Mar 14 [](https://www.expedia.ca/Lexington-Hotels-Value-Stay.h108675613.Hotel-Information) ![2 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108570000/108566500/108566456/42a5ffb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108570000/108566500/108566456/fce36096.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108570000/108566500/108566456/cef55aa6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/109000000/108570000/108566500/108566456/8b2dee1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Perch - NEW / Downtown! [](https://www.expedia.ca/Lexington-Hotels-The-Perch-NEW-Downtown.h108566456.Hotel-Information) Winchester 10/10 Exceptional (2 reviews) "The place was amazing! Very clean and comfortable. Great Italian restaurant down the street. Delicious dounuts around the corner.We went down to go into Lexington for Bourbon and wine tours. Would have liked to have a folder/ binder with information on what is in the area ( we did explore downtown) and also for information about checking out.We had 4 adults and could have used more towels (had 1 towel for each person) But we did make due.All in all would give this place 5 stars! We will be... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angela G. CA $165 CA $358 total includes taxes & fees Mar 11 - Mar 12 [](https://www.expedia.ca/Lexington-Hotels-The-Perch-NEW-Downtown.h108566456.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) ![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) ![Lobby](https://images.trvl-media.com/lodging/1000000/430000/422700/422677/f8cf164e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/430000/422700/422677/c7af9b8d.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) ![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) ![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) ![Lobby](https://images.trvl-media.com/lodging/1000000/330000/327900/327866/acf9d056.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) ![Terrace/patio](https://images.trvl-media.com/lodging/125000000/124300000/124291200/124291174/d5c66ddf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/125000000/124300000/124291200/124291174/c2c3dbdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/125000000/124300000/124291200/124291174/73ff2855.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/125000000/124300000/124291200/124291174/f96a5f55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fantastic 4-bedroom farmhouse with AC in charming Winchester [](https://www.expedia.ca/Winchester-Hotels-Fantastic-4-Bedroom-Farmhouse-With-AC-In-Charming-Winchester.h124291174.Hotel-Information) Winchester CA $219 CA $360 total includes taxes & fees Mar 15 - Mar 16 [](https://www.expedia.ca/Winchester-Hotels-Fantastic-4-Bedroom-Farmhouse-With-AC-In-Charming-Winchester.h124291174.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/67000000/66880000/66878300/66878219/407bde99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/67000000/66880000/66878300/66878219/10872d54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, foosball, books, stereo](https://images.trvl-media.com/lodging/67000000/66880000/66878300/66878219/8dbf1655.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/67000000/66880000/66878300/66878219/bad93586.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min. [](https://www.expedia.ca/Winchester-Hotels-Family-And-Friends-At-Franklin-Ridge-Farms.h66878219.Hotel-Information) Winchester 10/10 Exceptional (42 reviews) "This home was beautiful and the hosts were overly generous with the amenities at the property. If we’re ever in the area again we will definitely be staying here! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Josiah C. CA $332 CA $451 total includes taxes & fees Feb 25 - Feb 26 [](https://www.expedia.ca/Winchester-Hotels-Family-And-Friends-At-Franklin-Ridge-Farms.h66878219.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103570000/103570000/103569999/w511h683x255y0-43dbacf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/104000000/103570000/103570000/103569999/w508h683x259y0-958562e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/104000000/103570000/103570000/103569999/w508h683x258y0-7896e0d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/104000000/103570000/103570000/103569999/w918h683x47y0-3062291a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 4 Bed 3 bath clean , spacious all brick home , welcome families and work groups [](https://www.expedia.ca/Lexington-Hotels-4-Bed-3-Bath-Clean.h103569999.Hotel-Information) Winchester 9.8/10 Exceptional (7 reviews) "Easy check in, Clean and close to everything. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vicky R. CA $179 CA $396 total includes taxes & fees Feb 25 - Feb 26 [](https://www.expedia.ca/Lexington-Hotels-4-Bed-3-Bath-Clean.h103569999.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 ![Fairfield Inn & Suites by Marriott Lexington North](https://images.trvl-media.com/lodging/3000000/2810000/2803700/2803646/6ec64b2f_y.jpg) ### Fairfield Inn & Suites by Marriott Lexington North 10/10 Excellent "Nice room. Very courteous staff" [](https://expedia.ca/Lexington-Hotels-Fairfield-Inn-Suites-By-Marriott-Lexington-North.h2803646.Hotel-Information) ![Elwood Hotel & Suites](https://images.trvl-media.com/lodging/3000000/2220000/2219800/2219782/f131bcc5_y.jpg) ### Elwood Hotel & Suites 10/10 Excellent "Room was very clean and spacious " [](https://expedia.ca/Lexington-Hotels-Elwood-Hotel-Suites.h2219782.Hotel-Information) ![Quality Inn Lexington -Horse Park](https://images.trvl-media.com/lodging/1000000/30000/22700/22656/6339efc4_y.jpg) ### Quality Inn Lexington -Horse Park 10/10 Excellent "Very nice conveniently located and very afford will stay here every time I come to Lexington " [](https://expedia.ca/Lexington-Hotels-Quality-Inn-Lexington.h22656.Hotel-Information) ![Embassy Suites by Hilton Lexington Green](https://images.trvl-media.com/lodging/1000000/10000/1600/1598/1dd182aa_y.jpg) ### Embassy Suites by Hilton Lexington Green 10/10 Excellent "The room was clean, the bed was comfortable and the staff were friendly. I would stay again!" [](https://expedia.ca/Lexington-Hotels-Embassy-Suites-By-Hilton-Lexington-Green.h1598.Hotel-Information) ![Country Inn & Suites by Radisson, Georgetown, KY](https://images.trvl-media.com/lodging/1000000/540000/532100/532007/2dacd96b_y.jpg) ### Country Inn & Suites by Radisson, Georgetown, KY 10/10 Excellent "This motel is absolutely off the chain !! OMG would recommend it over and over again." [](https://expedia.ca/Lexington-Hotels-Country-Inn-Suites-By-Radisson.h532007.Hotel-Information) ![The Campbell House Lexington, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/30000/27100/27029/2fd2c43b_y.jpg) ### The Campbell House Lexington, Curio Collection by Hilton 10/10 Excellent "Comfortable clean room, excellent dinner restaurant (Tavern), good complimentary breakfast." [](https://expedia.ca/Lexington-Hotels-The-Campbell-House-Lexington.h27029.Hotel-Information) ![Hyatt Regency Lexington](https://images.trvl-media.com/lodging/1000000/10000/3500/3461/c0c49295_y.jpg) ### Hyatt Regency Lexington 10/10 Excellent "The room was great, and the place was very convenient. " [](https://expedia.ca/Lexington-Hotels-Hyatt-Regency-Lexington.h3461.Hotel-Information) ![DoubleTree Suites by Hilton Hotel Lexington](https://images.trvl-media.com/lodging/1000000/10000/9900/9900/f18d8c34_y.jpg) ### DoubleTree Suites by Hilton Hotel Lexington 10/10 Excellent "Room was clean front desk staff was great - breakfast was a tad weird as they don’t explain it to you and also wish it was free bar was good bar tender is was a bit quiet and not interactive but overall good stay 8/10 " [](https://expedia.ca/Lexington-Hotels-DoubleTree-Suites-By-Hilton-Hotel-Lexington.h9900.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Lexington South / Hamburg](https://images.trvl-media.com/lodging/1000000/290000/283200/283165/8b90557f_y.jpg) ### La Quinta Inn & Suites by Wyndham Lexington South / Hamburg 10/10 Excellent "Clean room, lady at the front desk was kind and welcoming at 9:30 pm. The pool was warm, no need for a hot tub. Our stay was great after a long drive. 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