Title: Book the Best Winchester FAMILY FRIENDLY Hotels from CA $86 - Kid-Friendly Hotels in Winchester, KY | 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 # Find Family Hotels in Winchester, KY from CA $86 - ![](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 Family Hotels Tonight [Nov 29 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2025-11-29&endDate=2025-11-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Tomorrow [Nov 30 - Dec 1](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2025-11-30&endDate=2025-12-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Next weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2025-12-05&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) In two weeks [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) ## Top Winchester Family Hotels ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/20000/15300/15247/690f0ff1.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/cbda8326.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/15300/15247/5bc6f945.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/15300/15247/8485fa77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Winchester Hotel Winchester 8.4/10 Very good (1002) "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 $101 CA $111 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Lexington-Hotels-Best-Western-Winchester-Hotel.h15247.Hotel-Information) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/16300/16227/b2646625.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/20000/16300/16227/09a180f7.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 Winchester 9.2/10 Wonderful (449) "Would stay there again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patricia CA $145 CA $160 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Lexington-Hotels-Hampton-Inn-Winchester.h16227.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/430000/422700/422677/ffbaf3eb.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) ![Desk, laptop workspace, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/430000/422700/422677/2b5cc63d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Baymont by Wyndham Winchester Winchester 7.2/10 Good (769) "The room was all that we expected very good. Staff was very friendly." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) LEROY CA $100 CA $110 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Lexington-Hotels-Baymont-By-Wyndham-Winchester.h422677.Hotel-Information) ![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/330000/327900/327866/2f002c60.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) ![Breakfast area](https://images.trvl-media.com/lodging/1000000/330000/327900/327866/1ed60932.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/330000/327900/327866/9eec7934.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn Winchester Winchester 7.0/10 Good (351) " Nice, new facilities" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Francis CA $87 CA $96 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Lexington-Hotels-Comfort-Inn.h327866.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/109000000/108680000/108675700/108675613/60df97aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108680000/108675700/108675613/w2880h1620x0y150-42668226.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) ![Reception](https://images.trvl-media.com/lodging/109000000/108680000/108675700/108675613/812dcf31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Value Stay Winchester 7.8/10 Good (124) "Awesome rooms and service" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brandon CA $78 CA $86 total includes taxes & fees Dec 27 - Dec 28 [](https://www.expedia.ca/Lexington-Hotels-Value-Stay.h108675613.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5900/5872/6ff0bc67.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/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/1000000/10000/5900/5872/7e83f7ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Red Roof Inn Winchester - Lexington East Winchester 6.6/10 (584) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Walter CA $87 CA $96 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Lexington-Hotels-Red-Roof-Inn-Lexington-Winchester.h5872.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/67000000/66880000/66878300/66878219/c58d578a.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/67000000/66880000/66878300/66878219/w1125h804x0y0-3754d269.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/67000000/66880000/66878300/66878219/b844ffc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min. Winchester 10/10 Exceptional (42) "Beautiful location and great service. The owner was very responsive and provided great value for the stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Spencer H. CA $339 CA $460 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Winchester-Hotels-Family-And-Friends-At-Franklin-Ridge-Farms.h66878219.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/77000000/76790000/76787000/76786917/0099ee0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76790000/76787000/76786917/7d4757fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, laptop workspace, iron/ironing board](https://images.trvl-media.com/lodging/77000000/76790000/76787000/76786917/77411ac7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/77000000/76790000/76787000/76786917/6c3e22b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Staybridge Suites Lexington S Medical Ctr Area by IHG Lexington 9.8/10 Exceptional (472) "Nice stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) george CA $107 CA $124 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Lexington-Hotels-Staybridge-Suites-Lexington-S-Medical-Ctr-Area.h76786917.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/290000/283200/283165/8b90557f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/290000/283200/283165/d8551f34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/290000/283200/283165/10569f88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/290000/283200/283165/a68d39be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Lexington South / Hamburg Lexington 8.8/10 Excellent (1229) "Had a wonderful stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tara CA $106 CA $123 total includes taxes & fees Dec 25 - Dec 26 [](https://www.expedia.ca/Lexington-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Lexington-South-Hamburg.h283165.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/102000000/101180000/101171900/101171857/89ad308c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, free WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101180000/101171900/101171857/efb0d5e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/102000000/101180000/101171900/101171857/0d0905b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/102000000/101180000/101171900/101171857/95b4cfd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Everhome Suites Lexington - Horse Park Lexington 9.2/10 Wonderful (389) "Great place to stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristin CA $112 CA $129 total includes taxes & fees Dec 27 - Dec 28 [](https://www.expedia.ca/Lexington-Hotels-Everhome-Suites-Lexington-North.h101171857.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=2025-12-13&endDate=2025-12-14®ionId=7876&adults=2&travelerType=family_friendly&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AFFINITY_BF_PROMO_7876) ## Top Winchester Hotel Reviews ![Spark by Hilton Lexington Hamburg](https://images.trvl-media.com/lodging/1000000/10000/6700/6639/4dbc3493_y.jpg) ### Spark by Hilton Lexington Hamburg 10/10 Excellent "Staff was super friendly, beds were nice and rooms were clean. " [](https://expedia.ca/Lexington-Hotels-Spark-By-Hilton-Lexington-Hamburg.h6639.Hotel-Information) ![Embassy Suites by Hilton Lexington/UK Coldstream](https://images.trvl-media.com/lodging/1000000/210000/203600/203587/32ffb492_y.jpg) ### Embassy Suites by Hilton Lexington/UK Coldstream 10/10 Excellent "There was construction. However, it was not bad at all! I would come back anytime. " [](https://expedia.ca/Lexington-Hotels-Embassy-Suites-By-Hilton-LexingtonUK-Coldstream.h203587.Hotel-Information) ![Comfort Inn & Suites Lexington - Hamburg I-75](https://images.trvl-media.com/lodging/1000000/30000/27400/27364/25d8ec98_y.jpg) ### Comfort Inn & Suites Lexington - Hamburg I-75 10/10 Excellent "Very clean room and super nice front desk employees. " [](https://expedia.ca/Lexington-Hotels-Comfort-Inn-Suites.h27364.Hotel-Information) ![GuestHouse Lexington](https://images.trvl-media.com/lodging/1000000/430000/426400/426325/18dc9903_y.jpg) ### GuestHouse Lexington 10/10 Excellent "a clean hotel and everything’s around, i would stay here again!" [](https://expedia.ca/Lexington-Hotels-GuestHouse-Lexington.h426325.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 "Very clean" [](https://expedia.ca/Lexington-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Lexington-South-Hamburg.h283165.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 "Clean room, great breakfast, welcoming staff." [](https://expedia.ca/Lexington-Hotels-Embassy-Suites-By-Hilton-Lexington-Green.h1598.Hotel-Information) ![Best Western Winchester Hotel](https://images.trvl-media.com/lodging/1000000/20000/15300/15247/690f0ff1_y.jpg) ### Best Western Winchester Hotel 10/10 Excellent "This is our 2nd time staying here. Convenient stop on our trip. Rooms are clean and well maintained. The night check in guy Jared was very friendly & helpful. " [](https://expedia.ca/Lexington-Hotels-Best-Western-Winchester-Hotel.h15247.Hotel-Information) ![Hilton Lexington/Downtown](https://images.trvl-media.com/lodging/1000000/10000/2200/2101/b9ab6063_y.jpg) ### Hilton Lexington/Downtown 10/10 Excellent "Great atmosphere and room was clean and comfy beds" [](https://expedia.ca/Lexington-Hotels-Hilton-LexingtonDowntown.h2101.Hotel-Information) ![Elwood Hotel & Suites](https://images.trvl-media.com/lodging/3000000/2220000/2219800/2219782/f131bcc5_y.jpg) ### Elwood Hotel & Suites 10/10 Excellent "Friendly staff Easy check in Clean rooms" [](https://expedia.ca/Lexington-Hotels-Elwood-Hotel-Suites.h2219782.Hotel-Information) ## Frequently asked questions ### What's Winchester like for family-friendly vacations? > The welcoming destination of Winchester is a great choice if you've been thinking about a vacation with the kids. The excursions, football games, and cafes are just some of the things that make this an attractive family vacation spot. Arrange a flight into Blue Grass Airport (LEX), which is located 23 mi (37.1 km) from the city center. ### What's the best place to stay for families in Winchester? > [Hampton Inn Winchester](https://www.expedia.ca/Lexington-Hotels-Hampton-Inn-Winchester.h16227.Hotel-Information) is a hotel with free parking and free breakfast, and it's a top choice on Expedia for families. ### When's the best time to book a family-friendly vacation in Winchester? > The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Winchester is 56 inches. ### What's there to see and do with your family in Winchester? > While you are visiting Winchester, you might want to round up the kiddos and make time to see interesting attractions such as Clark County Public Library and Lexington Sporting Club Youth Complex. 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