Title: Book the Best Winchester FAMILY FRIENDLY Hotels from CA $91 - 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) ![](https://mediaim.expedia.com/destination/2/2d4532767bd47b707b21acca86317ffc.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Hyelsinta # Find Family Hotels in Winchester, KY from CA $91 ![](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 [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2025-10-14&endDate=2025-10-15&adults=2&travelerType=FAMILY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 15 - Oct 16](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2025-10-15&endDate=2025-10-16&adults=2&travelerType=FAMILY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2025-10-17&endDate=2025-10-19&adults=2&travelerType=FAMILY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2025-10-24&endDate=2025-10-26&adults=2&travelerType=FAMILY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## 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) ![Room amenity](https://images.trvl-media.com/lodging/1000000/20000/15300/15247/6f58ef98.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) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/15300/15247/80f943aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Winchester Hotel Winchester 8.4/10 Very good (983) "Firm bed, clean room, friendly staff and adequate breakfast. " CA $113 CA $125 total includes taxes & fees Nov 2 - Nov 3 [](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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/16300/16227/93f7fc7d.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) ### Hampton Inn Winchester Winchester 9.2/10 Wonderful (444) "Breakfast was really good! " CA $161 CA $178 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Lexington-Hotels-Hampton-Inn-Winchester.h16227.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) ![Exterior](https://images.trvl-media.com/lodging/109000000/108680000/108675700/108675613/0538137e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, 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) ### Value Stay Winchester 8.0/10 Very good (104) "Staff was friendly. The room was clean." CA $83 CA $91 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Lexington-Hotels-Value-Stay.h108675613.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) ![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) ![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 (756) "The room was comfortable. The staff was helpful and accommodating. " CA $107 CA $118 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Lexington-Hotels-Baymont-By-Wyndham-Winchester.h422677.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) ![Vending machine](https://images.trvl-media.com/lodging/1000000/10000/5900/5872/e0cd2102.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 Winchester - Lexington East Winchester 6.6/10 (572) "Great stay" CA $87 CA $96 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Lexington-Hotels-Red-Roof-Inn-Lexington-Winchester.h5872.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/330000/327900/327866/9eec7934.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) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/330000/327900/327866/df000477.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn Winchester 7.0/10 Good (344) " Nice, new facilities" CA $101 CA $112 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Lexington-Hotels-Comfort-Inn.h327866.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) ![Exterior](https://images.trvl-media.com/lodging/67000000/66880000/66878300/66878219/3c5d5d4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Franklin Ridge Farms Winchester ; Lexington 20 min. & Stanton 15min. Winchester 10/10 Exceptional (38) "Beautiful farm . Amazing house " CA $340 CA $459 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Winchester-Hotels-Family-And-Friends-At-Franklin-Ridge-Farms.h66878219.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/130000/123900/123895/c0739f84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/1000000/130000/123900/123895/808e3fd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/130000/123900/123895/e3259f6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/130000/123900/123895/6370b2e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### GLō Best Western Lexington Lexington 9.4/10 Exceptional (2248) "Wonderful stay at this hotel!" CA $131 CA $152 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Lexington-Hotels-GLo-Best-Western-Lexington.h123895.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/810000/800900/800890/721376a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, pillowtop beds, desk](https://images.trvl-media.com/lodging/1000000/810000/800900/800890/9cc1d457.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/810000/800900/800890/77f13e33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/810000/800900/800890/04e3e24a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Richmond Richmond 8.8/10 Excellent (1019) "Clean, friendly staff, convenient, descent breakfast." CA $139 CA $153 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Lexington-Hotels-Quality-Inn.h800890.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/1000000/290000/283200/283165/5c80a240.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 (1202) "Had a wonderful stay" CA $122 CA $142 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Lexington-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Lexington-South-Hamburg.h283165.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=2025-10-28&endDate=2025-10-29®ionId=7876&adults=2&travelerType=family_friendly&sort=RECOMMENDED&openPlayBack=true) ## Top Winchester Hotel Reviews ![Embassy Suites by Hilton Lexington/UK Coldstream](//images.trvl-media.com/lodging/1000000/210000/203600/203587/32ffb492_y.jpg) ### Embassy Suites by Hilton Lexington/UK Coldstream 10/10 Excellent "Beautiful surroundings " [](https://expedia.ca/Lexington-Hotels-Embassy-Suites-By-Hilton-LexingtonUK-Coldstream.h203587.Hotel-Information) ![Hilton Lexington/Downtown](//images.trvl-media.com/lodging/1000000/10000/2200/2101/b9ab6063_y.jpg) ### Hilton Lexington/Downtown 10/10 Excellent "Wonderful. As expected. " [](https://expedia.ca/Lexington-Hotels-Hilton-LexingtonDowntown.h2101.Hotel-Information) ![Natural Bridge State Resort Park](//images.trvl-media.com/lodging/16000000/15440000/15437800/15437778/df7a7684_y.jpg) ### Natural Bridge State Resort Park 10/10 Excellent "We stayed in a cottage room and it was even nicer in person than in the photos! Also a very friendly staff at the lodge!" [](https://expedia.ca/Slade-Hotels-Natural-Bridge-State-Resort-Park.h15437778.Hotel-Information) ![Quality Inn Lexington -Horse Park](//images.trvl-media.com/lodging/1000000/30000/22700/22656/6339efc4_y.jpg) ### Quality Inn Lexington -Horse Park 10/10 Excellent "Good bang for your buck. Anytime I’m in the area I stay here" [](https://expedia.ca/Lexington-Hotels-Quality-Inn-Lexington.h22656.Hotel-Information) ![Elwood Hotel & Suites](//images.trvl-media.com/lodging/3000000/2220000/2219800/2219782/f131bcc5_y.jpg) ### Elwood Hotel & Suites 10/10 Excellent "Great stay!" [](https://expedia.ca/Lexington-Hotels-Elwood-Hotel-Suites.h2219782.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Lexington South / Hamburg](//images.trvl-media.com/lodging/1000000/290000/283200/283165/60f6cd78_y.jpg) ### La Quinta Inn & Suites by Wyndham Lexington South / Hamburg 10/10 Excellent "Clean room. Friendly staff. Good breakfast." [](https://expedia.ca/Lexington-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Lexington-South-Hamburg.h283165.Hotel-Information) ![Spark by Hilton Lexington Hamburg](//images.trvl-media.com/lodging/1000000/10000/6700/6639/4dbc3493_y.jpg) ### Spark by Hilton Lexington Hamburg 10/10 Excellent "Clean room and friendly staff " [](https://expedia.ca/Lexington-Hotels-Spark-By-Hilton-Lexington-Hamburg.h6639.Hotel-Information) ![GuestHouse Lexington](//images.trvl-media.com/lodging/1000000/430000/426400/426325/18dc9903_y.jpg) ### GuestHouse Lexington 10/10 Excellent "Clean room! Everything great! TV practically knew! Wi-Fi superb! A great bargain! Excellent, hot breakfast! I love the location!" [](https://expedia.ca/Lexington-Hotels-GuestHouse-Lexington.h426325.Hotel-Information) ![Hyatt Regency Lexington](//images.trvl-media.com/lodging/1000000/10000/3500/3461/c0c49295_y.jpg) ### Hyatt Regency Lexington 10/10 Excellent "Perfect location for Rupp Arena venue. Check in was quick and overall hotel was nice and clean. " [](https://expedia.ca/Lexington-Hotels-Hyatt-Regency-Lexington.h3461.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 Hamburg Pavilon. 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