Title: Book the Best Winchester FAMILY FRIENDLY Hotels from CA $89 - 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 ![](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 Family Hotels Tonight [Mar 3 - Mar 4](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-03-03&endDate=2026-03-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Tomorrow [Mar 4 - Mar 5](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-03-04&endDate=2026-03-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) This weekend [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-03-06&endDate=2026-03-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Next weekend [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-03-13&endDate=2026-03-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) ## Our top choices for Winchester family-friendly hotels ![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/109000000/108680000/108675700/108675613/33a8f318.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) ![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 $80 CA $89 total includes taxes & fees Mar 5 - Mar 6 [](https://www.expedia.ca/Lexington-Hotels-Value-Stay.h108675613.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) ![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) ![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 (1,001 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 $110 CA $122 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Lexington-Hotels-Best-Western-Winchester-Hotel.h15247.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) ![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/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) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/16300/16227/51af70a1.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) ![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) ### Hampton Inn Winchester [](https://www.expedia.ca/Lexington-Hotels-Hampton-Inn-Winchester.h16227.Hotel-Information) Winchester 9.2/10 Wonderful (457 reviews) "Would stay there again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patricia CA $180 CA $198 total includes taxes & fees Mar 30 - Mar 31 [](https://www.expedia.ca/Lexington-Hotels-Hampton-Inn-Winchester.h16227.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) ![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 $100 CA $110 total includes taxes & fees Mar 29 - Mar 30 [](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) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/5900/5872/ed324e5a.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) ### 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 23 - Mar 24 [](https://www.expedia.ca/Lexington-Hotels-Red-Roof-Inn-Lexington-Winchester.h5872.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) ![Interior](https://images.trvl-media.com/lodging/67000000/66880000/66878300/66878219/bad93586.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/c361c57d.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) ### 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 $450 total includes taxes & fees Mar 4 - Mar 5 [](https://www.expedia.ca/Winchester-Hotels-Family-And-Friends-At-Franklin-Ridge-Farms.h66878219.Hotel-Information) ![Interior entrance](https://images.trvl-media.com/lodging/1000000/810000/800900/800890/ecb98882.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/810000/800900/800890/a83dfff4.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) ![Premium bedding, pillowtop beds, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/810000/800900/800890/9cc1d457.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Richmond [](https://www.expedia.ca/Lexington-Hotels-Quality-Inn.h800890.Hotel-Information) Richmond 9.0/10 Wonderful (1,005 reviews) "Clean room, friendly staff, quiet" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marjorie CA $131 CA $145 total includes taxes & fees Mar 17 - Mar 18 [](https://www.expedia.ca/Lexington-Hotels-Quality-Inn.h800890.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/540000/532700/532630/991791b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/540000/532700/532630/9eb9f751.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking, Jetted Tub (Living Room;with Sofabed)](https://images.trvl-media.com/lodging/1000000/540000/532700/532630/913dc086.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/540000/532700/532630/686015f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Georgetown Corporate Center Hotel [](https://www.expedia.ca/Lexington-Hotels-Best-Western-Plus-Georgetown-Corporate-Center-Hotel.h532630.Hotel-Information) Georgetown 8.8/10 Excellent (1,002 reviews) "Clean room and the staff was very friendly and helpful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jim CA $109 CA $121 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Lexington-Hotels-Best-Western-Plus-Georgetown-Corporate-Center-Hotel.h532630.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/42500/42465/ccddf4e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/42500/42465/1f5a8411.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/50000/42500/42465/0351fa56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed with Sofa bed, Non Smoking, Hot Tub](https://images.trvl-media.com/lodging/1000000/50000/42500/42465/9655e087.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Baymont by Wyndham Georgetown/Lexington North [](https://www.expedia.ca/Lexington-Hotels-Baymont-By-Wyndham-Georgetown.h42465.Hotel-Information) Georgetown 8.0/10 Very good (1,004 reviews) "Staff was very friendly and the room was very clean and comfortable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mayme CA $98 CA $108 total includes taxes & fees Mar 4 - Mar 5 [](https://www.expedia.ca/Lexington-Hotels-Baymont-By-Wyndham-Georgetown.h42465.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=2026-03-17&endDate=2026-03-18®ionId=7876&adults=2&travelerType=family_friendly&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at family-friendly hotels in Winchester Pool Breakfast included All-inclusive 4 stars 5 stars ![](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 ![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 "La habitación estaba impecable y el personal muy amable " [](https://expedia.ca/Lexington-Hotels-Quality-Inn-Lexington.h22656.Hotel-Information) ![Marriott Lexington Griffin Gate Golf Resort & Spa](https://images.trvl-media.com/lodging/1000000/20000/15900/15892/79f835ef_y.jpg) ### Marriott Lexington Griffin Gate Golf Resort & Spa 10/10 Excellent "From check-in to check-out, the overall experience was great. The staff are all friendly and so helpful. " [](https://expedia.ca/Lexington-Hotels-Lexington-Griffin-Gate-Marriott-Golf-Resort-Spa.h15892.Hotel-Information) ![Elwood Hotel & Suites](https://images.trvl-media.com/lodging/3000000/2220000/2219800/2219782/f131bcc5_y.jpg) ### Elwood Hotel & Suites 10/10 Excellent "The folks at Elwood showed true Southern hospitality—polite, hardworking, and respectful from the minute we walked in. No nonsense, just good old-fashioned service that made us feel welcome like we belonged. Room was clean, bed comfortable, everything in order and cozy enough to rest well after a full day. Solid place all around, no complaints. If you’re in Lexington—whether for the track, bourbon, or just passing through—this is the spot. We’ll be back. Strongly recommend." [](https://expedia.ca/Lexington-Hotels-Elwood-Hotel-Suites.h2219782.Hotel-Information) ![Hyatt Regency Lexington](https://images.trvl-media.com/lodging/1000000/10000/3500/3461/c0c49295_y.jpg) ### Hyatt Regency Lexington 10/10 Excellent "Check in was quick and easy and the valet parking was a life saver! " [](https://expedia.ca/Lexington-Hotels-Hyatt-Regency-Lexington.h3461.Hotel-Information) ![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 "The Staff was great. Everything was as to be expected for Marriott." [](https://expedia.ca/Lexington-Hotels-Fairfield-Inn-Suites-By-Marriott-Lexington-North.h2803646.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 "Cleanliness and friendliness " [](https://expedia.ca/Lexington-Hotels-Country-Inn-Suites-By-Radisson.h532007.Hotel-Information) ![Clarion Hotel Conference Center Lexington North](https://images.trvl-media.com/lodging/1000000/30000/25900/25887/d2bb2f78_y.jpg) ### Clarion Hotel Conference Center Lexington North 10/10 Excellent "Great amenities" [](https://expedia.ca/Lexington-Hotels-Clarion-Hotel-Conference-Center-North.h25887.Hotel-Information) ![Natural Bridge State Resort Park](https://images.trvl-media.com/lodging/16000000/15440000/15437800/15437778/324d2660_y.jpg) ### Natural Bridge State Resort Park 10/10 Excellent "We had a great stay, primarily because of the bartender. He is very personable. We had only stopped in for an after dinner drink, and ended up closing tge place. 😆 He told us about a delicious sounding drink recipe that contained root beer. We happened to have some bottles of root beer with us that we had purchased at one of of the bourbon tours - we got them and brought them to the bar and he made the drinks which we then shared with other guests. In return, we shared with him a new drink we had created elsewhere that we named the Happy Traveler. I look forward to going back one day and hopefully seeing our drink on his menu. We would legit stay here again just to hang out at the bar. Otherwise, I would have given three stars because of the dinner experience. The staff there were very nice, but I ordered chicken and it came out raw. Had to send it back, they made it again, and it came out raw a second time. That’s actually why we went to the bar, to grab a drink and some bar snacks cuz I was hangry! lol " [](https://expedia.ca/Slade-Hotels-Natural-Bridge-State-Resort-Park.h15437778.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 "Everything was nice. " [](https://expedia.ca/Lexington-Hotels-DoubleTree-Suites-By-Hilton-Hotel-Lexington.h9900.Hotel-Information) ## Frequently asked questions ### What's Winchester like for family-friendly vacations? ### What's the best place to stay for families in Winchester? ### When's the best time to book a family-friendly vacation in Winchester? ### What's there to see and do with your family in Winchester? ## 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) - 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