Title: Book The Best Hotels in Winchester, KY for 2026 from CA $89 - Fully Refundable Options - Expedia.ca [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/ozark-mountains-arkansas-limestone-bluff-clear-creek-autumn.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/ozark-mountains-arkansas-limestone-bluff-clear-creek-autumn.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 ## Go beyond your typical stay in Winchester Pool [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Kentucky%2C+United+States+of+America®ionId=7876&latLong=37.990078%2C-84.179649&adults=2&startDate=2026-02-05&d1=2026-02-05&endDate=2026-02-07&d2=2026-02-07&amenities=POOL) Hot tub [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Kentucky%2C+United+States+of+America®ionId=7876&latLong=37.990078%2C-84.179649&adults=2&startDate=2026-02-05&d1=2026-02-05&endDate=2026-02-07&d2=2026-02-07&amenities=HOT_TUB) Pet friendly [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Kentucky%2C+United+States+of+America®ionId=7876&latLong=37.990078%2C-84.179649&adults=2&startDate=2026-02-05&d1=2026-02-05&endDate=2026-02-07&d2=2026-02-07&amenities=PETS) Cabin [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Kentucky%2C+United+States+of+America®ionId=7876&latLong=37.990078%2C-84.179649&adults=2&startDate=2026-02-05&d1=2026-02-05&endDate=2026-02-07&d2=2026-02-07&lodging=CABIN) Family friendly [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Kentucky%2C+United+States+of+America®ionId=7876&latLong=37.990078%2C-84.179649&adults=2&startDate=2026-02-05&d1=2026-02-05&endDate=2026-02-07&d2=2026-02-07&travelerType=family_friendly) Farm [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Kentucky%2C+United+States+of+America®ionId=7876&latLong=37.990078%2C-84.179649&adults=2&startDate=2026-02-05&d1=2026-02-05&endDate=2026-02-07&d2=2026-02-07&lodging=AGRITOURISM) Apart­ment [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Kentucky%2C+United+States+of+America®ionId=7876&latLong=37.990078%2C-84.179649&adults=2&startDate=2026-02-05&d1=2026-02-05&endDate=2026-02-07&d2=2026-02-07&lodging=APARTMENT) Condo [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Kentucky%2C+United+States+of+America®ionId=7876&latLong=37.990078%2C-84.179649&adults=2&startDate=2026-02-05&d1=2026-02-05&endDate=2026-02-07&d2=2026-02-07&lodging=CONDO) Cottage [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Kentucky%2C+United+States+of+America®ionId=7876&latLong=37.990078%2C-84.179649&adults=2&startDate=2026-02-05&d1=2026-02-05&endDate=2026-02-07&d2=2026-02-07&lodging=COTTAGE) ## Check prices for these dates Tonight [Jan 22 - Jan 23](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-01-22&endDate=2026-01-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 23 - Jan 24](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-01-23&endDate=2026-01-24&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-01-23&endDate=2026-01-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester hotels ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/25000000/24370000/24362600/24362582/a8fad05c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/25000000/24370000/24362600/24362582/3474fa42.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) ![Indoor pool](https://images.trvl-media.com/lodging/25000000/24370000/24362600/24362582/04a3c81a.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 9.4/10 Exceptional (537 reviews) "Clean room and friendly staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tyson CA $122 CA $134 total includes taxes & fees Jan 29 - Jan 30 [](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) ![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 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 $100 CA $110 total includes taxes & fees Jan 26 - Jan 27 [](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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/16300/16227/93f7fc7d.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) ![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) ### Hampton Inn Winchester [](https://www.expedia.ca/Lexington-Hotels-Hampton-Inn-Winchester.h16227.Hotel-Information) Winchester 9.2/10 Wonderful (455 reviews) "Would stay there again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patricia CA $146 CA $161 total includes taxes & fees Feb 15 - Feb 16 [](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/109000000/108680000/108675700/108675613/33a8f318.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) ![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 (127 reviews) "Awesome rooms and service" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brandon CA $93 CA $102 total includes taxes & fees Jan 23 - Jan 24 [](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 (775 reviews) "Great place for a reasonable price! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Whitney CA $105 CA $115 total includes taxes & fees Jan 25 - Jan 26 [](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) ![Breakfast area](https://images.trvl-media.com/lodging/1000000/330000/327900/327866/1ed60932.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) ### Comfort Inn Winchester [](https://www.expedia.ca/Lexington-Hotels-Comfort-Inn.h327866.Hotel-Information) Winchester 7.0/10 Good (354 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 Feb 13 - Feb 14 [](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) ![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 [](https://www.expedia.ca/Lexington-Hotels-Red-Roof-Inn-Lexington-Winchester.h5872.Hotel-Information) Winchester 6.4/10 (589 reviews) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Walter CA $86 CA $95 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Lexington-Hotels-Red-Roof-Inn-Lexington-Winchester.h5872.Hotel-Information) ![Indoor pool, open 5:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/130000/123900/123895/b7d6b7de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, memory foam beds, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/130000/123900/123895/43c15bef.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/a15dee33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/130000/123900/123895/8d79aa69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Lexington Horse Park Area by IHG [](https://www.expedia.ca/Lexington-Hotels-Holiday-Inn-Express-Lexington-Horse-Park-Area-By-IHG.h123895.Hotel-Information) Lexington 9.4/10 Exceptional (2,228 reviews) "Room was clean, staff was very helpful, easy parking, decent breakfast" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Christian CA $122 CA $141 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Lexington-Hotels-Holiday-Inn-Express-Lexington-Horse-Park-Area-By-IHG.h123895.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/540000/532100/532007/db3edf18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/540000/532100/532007/c2f8d65b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/540000/532100/532007/6399ecfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Non Smoking, Jetted Tub](https://images.trvl-media.com/lodging/1000000/540000/532100/532007/511a8efe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Inn & Suites by Radisson, Georgetown, KY [](https://www.expedia.ca/Lexington-Hotels-Country-Inn-Suites-By-Radisson.h532007.Hotel-Information) Georgetown 9.0/10 Wonderful (1,005 reviews) "Great stay! The hotel is clean, quite, and friendly. The breakfast bar was really good, too. Will definitely stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah CA $108 CA $119 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Lexington-Hotels-Country-Inn-Suites-By-Radisson.h532007.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/810000/800900/800890/e9f30778.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/810000/800900/800890/77f13e33.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 (1,011 reviews) "The room was clean and the bed was super comfortable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth CA $123 CA $136 total includes taxes & fees Jan 23 - Jan 24 [](https://www.expedia.ca/Lexington-Hotels-Quality-Inn.h800890.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 | 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) ![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 | Living area](https://images.trvl-media.com/lodging/16000000/15440000/15437800/15437778/fa7fc3aa.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 (1,795 reviews) "Friendly staff, convenient the have a restaurant and tavern on site. There is great hiking right out the back door. Appreciated a quiet stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kimberly [](https://www.expedia.ca/Slade-Hotels-Natural-Bridge-State-Resort-Park.h15437778.Hotel-Information) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/290000/283200/283165/8b1776b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/290000/283200/283165/8b90557f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed, Accessible, Non Smoking (Mobility/Hearing Impaired Accessible)](https://images.trvl-media.com/lodging/1000000/290000/283200/283165/a4d4a758.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) ### La Quinta Inn & Suites by Wyndham Lexington South / Hamburg [](https://www.expedia.ca/Lexington-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Lexington-South-Hamburg.h283165.Hotel-Information) Lexington 8.8/10 Excellent (1,204 reviews) "A very nice hotel " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dale CA $125 CA $145 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Lexington-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Lexington-South-Hamburg.h283165.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/50000/42500/42455/751708b8.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/42500/42455/81b02df3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee service](https://images.trvl-media.com/lodging/1000000/50000/42500/42455/a4118e3b.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 (711 reviews) "We stay here anytime we are in town " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Donn CA $93 CA $103 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Mount-Sterling-Hotels-Comfort-Inn-And-Suites.h42455.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/23000000/22760000/22757700/22757695/776ae294.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily cooked-to-order breakfast for a fee](https://images.trvl-media.com/lodging/23000000/22760000/22757700/22757695/9c05e321.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, desk](https://images.trvl-media.com/lodging/23000000/22760000/22757700/22757695/93711b8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/23000000/22760000/22757700/22757695/4fc5529c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Lexington - Hamburg by IHG [](https://www.expedia.ca/Lexington-Hotels-Holiday-Inn-Lexington-Hamburg.h22757695.Hotel-Information) Lexington 9.0/10 Wonderful (1,001 reviews) "Amazing staff especially the lady Nicki who went above and beyond for us during check in " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica CA $122 CA $141 total includes taxes & fees Jan 30 - Jan 31 [](https://www.expedia.ca/Lexington-Hotels-Holiday-Inn-Lexington-Hamburg.h22757695.Hotel-Information) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/90000000/89550000/89542000/89541948/9e14ddfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/90000000/89550000/89542000/89541948/d0867e8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/90000000/89550000/89542000/89541948/534e6b71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, 1 King Bed, Refrigerator & Microwave (Wet bar)](https://images.trvl-media.com/lodging/90000000/89550000/89542000/89541948/25d67f8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Nicholasville Brannon Crossing [](https://www.expedia.ca/Lexington-Hotels-Hampton-Inn-Nicholasville-Brannon-Crossing.h89541948.Hotel-Information) Nicholasville 9.4/10 Exceptional (248 reviews) "Very nice all around! Would stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dave CA $125 CA $138 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Lexington-Hotels-Hampton-Inn-Nicholasville-Brannon-Crossing.h89541948.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/80000/77700/77616/062c7033.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/80000/77700/77616/cc3a9c87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, iron/ironing board](https://images.trvl-media.com/lodging/1000000/80000/77700/77616/e3f86111.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/80000/77700/77616/3ba223d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Richmond [](https://www.expedia.ca/Lexington-Hotels-Hampton-Inn-Richmond.h77616.Hotel-Information) Richmond 9.2/10 Wonderful (1,003 reviews) "Clean hotel with friendly staff. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Susan CA $135 CA $149 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Lexington-Hotels-Hampton-Inn-Richmond.h77616.Hotel-Information) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/28000000/27530000/27529500/27529446/15a7c863.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Airport shuttle](https://images.trvl-media.com/lodging/28000000/27530000/27529500/27529446/976ed9c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Double Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/28000000/27530000/27529500/27529446/a4644fd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/28000000/27530000/27529500/27529446/9c5ead39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Asbury Inn & Suites [](https://www.expedia.ca/Wilmore-Hotels-Asbury-Inn-Suites.h27529446.Hotel-Information) Wilmore 9.6/10 Exceptional (491 reviews) "Room was clean, building was very quiet and I will definitely be staying at" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah CA $164 CA $181 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Wilmore-Hotels-Asbury-Inn-Suites.h27529446.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/24000000/23510000/23507600/23507536/1f95523f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/24000000/23510000/23507600/23507536/5efbd8e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/24000000/23510000/23507600/23507536/a365d5b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/24000000/23510000/23507600/23507536/a323e895.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Mt Sterling North by IHG [](https://www.expedia.ca/Mount-Sterling-Hotels-Holiday-Inn-Express-Suites-Mt-Sterling-North.h23507536.Hotel-Information) Mount Sterling 8.8/10 Excellent (581 reviews) "Room was super clean and the woman at the front desk was really nice and very helpful" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) mark CA $123 CA $136 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Mount-Sterling-Hotels-Holiday-Inn-Express-Suites-Mt-Sterling-North.h23507536.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/30000/24800/24727/57d602a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout drapes, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/1000000/30000/24800/24727/edf0b0af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/24800/24727/7cb09e1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/24800/24727/c41974d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Baymont by Wyndham Richmond KY [](https://www.expedia.ca/Lexington-Hotels-Baymont-By-Wyndham-Richmond-KY.h24727.Hotel-Information) Richmond 7.0/10 Good (1,000 reviews) "clean room nice hot tub friendly staff " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marissa CA $94 CA $104 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Lexington-Hotels-Baymont-By-Wyndham-Richmond-KY.h24727.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/11100/11045/78a9bd82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/11100/11045/0c9a99e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/20000/11100/11045/42bd58ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, laptop workspace, iron/ironing board](https://images.trvl-media.com/lodging/1000000/20000/11100/11045/d0e1f52b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Clarion Pointe Richmond North near University [](https://www.expedia.ca/Lexington-Hotels-Clarion-Pointe.h11045.Hotel-Information) Richmond 8.2/10 Very good (909 reviews) "Room was very clean, staff was very friendly " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jane CA $95 CA $104 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Lexington-Hotels-Clarion-Pointe.h11045.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=2026-02-05&endDate=2026-02-06®ionId=7876&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Hotels.d7876.Travel-Guide-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Hotels.d7876.Travel-Guide-Hotels) ## Learn more about Winchester Stroll through charming downtown streets lined with local shops and eateries. Tee off at Cassell Creek or Southwind Golf Course, then explore local history at the Bluegrass Heritage Museum. [See all hotels in Winchester](https://www.expedia.ca/Hotel-Search?startDate=2026-02-05&endDate=2026-02-06&adults=2®ionId=7876) ![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=300&h=400&p=1&q=high) Photo by Nawa Aseen ### Stay near popular Winchester attractions [](https://expedia.ca/University-Of-Kentucky-Hotels.0-l6062605-0.Travel-Guide-Filter-Hotels) ![A panoramic picture of the gorgeous University of Kentucky Campus.](https://images.trvl-media.com/place/2054/8ce86a9a-fc81-45d9-ac0e-63f81263f090.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### University of Kentucky Explore the campus of University of Kentucky, during your travels in Lexington. Attend a sporting event or simply enjoy the lively bars while you're in the area. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6062605) [](https://expedia.ca/Kentucky-Horse-Park-Hotels.0-l6062603-0.Travel-Guide-Filter-Hotels) ![Kentucky Horse Park showing land animals](https://images.trvl-media.com/place/6062603/def85b29-11a4-4658-9dd9-2740c5e40aee.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Kentucky Horse Park Enjoy a trip to Kentucky Horse Park and popular activities like horseback riding in Lexington. Attend a sporting event or simply enjoy the lively bars while you're in the area. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6062603) [](https://expedia.ca/Buffalo-Trace-Distillery-Hotels.0-l553248621587339578-0.Travel-Guide-Filter-Hotels) ![The bottling line for the special single barrel Blantons Bourbon. ](https://images.trvl-media.com/place/7262/a9276a3e-fd4a-44ad-bf04-3f76dcbda506.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Buffalo Trace Distillery You can take time to visit Buffalo Trace Distillery during your travels to Frankfort. You can seek out the hiking trails while in the area. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621587339578) [](https://expedia.ca/Fayette-Mall-Hotels.0-l6163982-0.Travel-Guide-Filter-Hotels) ![It's beginning to look a lot like Christmas.](https://images.trvl-media.com/place/2054/91726926-a952-4f72-aa18-b91307d79b27.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Fayette Mall You can find the perfect gifts to bring home at Fayette Mall during your stay in Lexington. Discover the area's acclaimed theater scene, or seek out its horseback riding. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6163982) [](https://expedia.ca/The-Kentucky-Castle-Hotels.0-l6062617-0.Travel-Guide-Filter-Hotels) ![0_130598195](https://images.trvl-media.com/place/6062617/89df42d7-84c0-459d-aea1-6dfd9b93a545.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### The Kentucky Castle Enjoy a trip to The Kentucky Castle and popular activities like horseback riding in Versailles. Attend a sporting event or simply enjoy the lively bars while you're in the area. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6062617) [](https://expedia.ca/Eastern-Kentucky-University-Hotels.0-l553248621559142164-0.Travel-Guide-Filter-Hotels) ![Messing around this morning ](https://images.trvl-media.com/place/6148/d3648b5e-8896-4bf8-98ef-3a688205f1d4.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Eastern Kentucky University Enjoy the collegiate vibe when you visit Eastern Kentucky University, during your travels in Richmond. While in this family-friendly area, you can savor the top-notch restaurants. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621559142164) ## More cheap stays in Winchester ![Super 8 by Wyndham Georgetown](https://images.trvl-media.com/lodging/1000000/460000/459900/459849/b2d6c903_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Super 8 by Wyndham Georgetown 250 Tiger Way Georgetown KY CA $81 CA $89 total Feb 1 - Feb 2 includes taxes & fees 8.2/10 Very Good! (1,000 reviews) [](https://expedia.ca/Lexington-Hotels-Super-8-By-Wyndham-Georgetown.h459849.Hotel-Information) ![Days Inn Lexington SE/Hamburg](https://images.trvl-media.com/lodging/1000000/10000/9600/9539/685edbce_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Days Inn Lexington SE/Hamburg 5575 Athens Boonesboro Rd Lexington KY CA $79 CA $91 total Feb 2 - Feb 3 includes taxes & fees 7/10 Good! (1,002 reviews) [](https://expedia.ca/Lexington-Hotels-Days-Inn-By-Wyndham-Lexington-Southeast.h9539.Hotel-Information) ![Quality Inn Lexington -Horse Park](https://images.trvl-media.com/lodging/1000000/30000/22700/22656/6339efc4_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Quality Inn Lexington -Horse Park 1938 Stanton Way Lexington KY CA $95 CA $110 total Feb 9 - Feb 10 includes taxes & fees 8/10 Very Good! (1,639 reviews) [](https://expedia.ca/Lexington-Hotels-Quality-Inn-Lexington.h22656.Hotel-Information) ![GuestHouse Lexington](https://images.trvl-media.com/lodging/1000000/430000/426400/426325/18dc9903_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### GuestHouse Lexington 2261 Elkhorn Road Lexington KY CA $99 CA $115 total Jan 25 - Jan 26 includes taxes & fees 8.2/10 Very Good! (1,529 reviews) [](https://expedia.ca/Lexington-Hotels-GuestHouse-Lexington.h426325.Hotel-Information) ![Tru by Hilton University Medical Center](https://images.trvl-media.com/lodging/79000000/78010000/78004900/78004839/9823f52b_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Tru by Hilton University Medical Center 535 Waller Avenue Lexington KY CA $124 CA $144 total Jan 28 - Jan 29 includes taxes & fees 9.2/10 Wonderful! (569 reviews) [](https://expedia.ca/Lexington-Hotels-Tru-By-Hilton-Lexington-University-Medical-Center.h78004839.Hotel-Information) ![Everhome Suites Lexington - Horse Park](https://images.trvl-media.com/lodging/102000000/101180000/101171900/101171857/89ad308c_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Everhome Suites Lexington - Horse Park 757 Newtown Springs Drive Lexington KY CA $130 CA $151 total Jan 25 - Jan 26 includes taxes & fees 9.2/10 Wonderful! (453 reviews) [](https://expedia.ca/Lexington-Hotels-Everhome-Suites-Lexington-North.h101171857.Hotel-Information) ## Hotels in Winchester with star-rating ![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/23700/23677/6ae928dd_z.jpg) 4 Star Hotels 7 properties [](https://expedia.ca/4Star-Winchester-Hotels.s40-0-d7876.Travel-Guide-Filter-Hotels) ![3 Star Hotels](https://images.trvl-media.com/lodging/20000000/19690000/19681400/19681371/84fffc75_z.jpg) 3 Star Hotels 84 properties [](https://expedia.ca/3Star-Winchester-Hotels.s30-0-d7876.Travel-Guide-Filter-Hotels) ![2 Star Hotels](https://images.trvl-media.com/lodging/92000000/91830000/91828000/91827910/6717a2ac_z.jpg) 2 Star Hotels 196 properties [](https://expedia.ca/2Star-Winchester-Hotels.s20-0-d7876.Travel-Guide-Filter-Hotels) ## Find out more about Winchester ### Top reasons to visit Winchester - **Outdoor Adventures:** Winchester is a haven for outdoor enthusiasts, featuring beautiful hiking trails and scenic views in local parks. - **Charming Local Vibes:** Experience the friendly atmosphere while exploring quaint shops and attractions throughout the city. - **Rich Cultural Experiences:** Discover the area's history through various historic sites that offer a glimpse into the past. - **Family-Friendly Activities:** Winchester provides numerous excursions and activities suitable for families, ensuring fun for all ages. - **Affordable Accommodations:** Enjoy a range of budget-friendly motels and comfortable hotels, perfect for any traveller's needs. ### Find great hotels in Winchester Explore a variety of hotel accommodations in Winchester, Kentucky, perfect for every traveller. From budget-friendly motels to comfortable 2 to 3-star hotels, Winchester caters to business, family, and pet-friendly themes. Whether you're seeking hotels in Winchester or looking for options nearby, you'll find a welcoming stay that suits your needs and enhances your vacation experience. - **[Hyatt Place Lexington:](https://www.expedia.ca/Lexington-Hotels-Hyatt-Place-Lexington.h2057644.Hotel-Information)** Located 20.9km from Winchester, Hyatt Place Lexington offers a family-friendly and versatile environment for both leisure and business travelers. This 3-star hotel boasts a range of amenities tailored for business needs, including multiple meeting rooms and a 24-hour business centre. Families will appreciate the free crib service, while pet owners can bring their furry friends along, subject to specific restrictions. The hotel seamlessly blends comfort and convenience, making it an excellent choice for your stay. - **[GuestHouse Lexington:](https://www.expedia.ca/Lexington-Hotels-GuestHouse-Lexington.h426325.Hotel-Information)** Situated 22.5km from Winchester, GuestHouse Lexington presents a welcoming atmosphere ideal for families and business visitors alike. The hotel features a business centre, perfect for those needing to catch up on work while away. Safety is a priority, with amenities like window guards and a first aid kit available for families. Although it may not be as pet-friendly as others, it still offers a comfortable and functional space for all guests seeking a pleasant experience. - **[La Quinta Inn & Suites by Wyndham Lexington South / Hamburg:](https://www.expedia.ca/Lexington-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Lexington-South-Hamburg.h283165.Hotel-Information)** Positioned 17.7km from Winchester, La Quinta Inn & Suites combines family, pet, and business-friendly features in one convenient location. This hotel includes a 24-hour business centre and a meeting room, catering to the needs of travelling professionals. Families can take advantage of complimentary cribs while pets are welcome, with various policies in place for dogs and cats. With its array of amenities, La Quinta Inn & Suites ensures a comfortable stay for everyone. ### Where to stay in Winchester Winchester, Kentucky, offers a delightful mix of outdoor adventures and charming scenery, making it an ideal vacation spot. Visitors can enjoy friendly local vibes while exploring quaint shops and nearby attractions. It's a great base for getaways to places like Peak Spring Hill, providing opportunities for excursions and family-friendly activities. With affordable accommodations within walking distance, you'll find everything you need for a memorable stay in this welcoming city. - **[Lexington:](https://www.expedia.ca/Lexington-Hotels.d603003.Travel-Guide-Hotels)** A vibrant metropolis, Lexington is located a short drive from Winchester and offers a diverse travel experience. Known for its outdoor adventures, families flock here for recreational activities like hiking and camping. During your visit, explore the local parks and national state parks that dot the landscape. Don’t miss catching a game at the stadium, which serves as a hub for sports enthusiasts. With a steady influx of visitors throughout the year, Lexington is particularly lively from July to August and in October, making it an ideal stop for any traveller looking to immerse themselves in Kentucky's culture and natural beauty. - **[Clintonville:](https://www.expedia.ca/Clintonville-Hotels.d553248635975850573.Travel-Guide-Hotels)** Just 12.9km from Winchester, Clintonville is a charming village that captivates visitors with its scenic landscapes and outdoor activities. The area is perfect for those seeking adventure, whether it's hiking along picturesque trails or enjoying a relaxing day at the local campground. Golf enthusiasts will find excellent courses to play, while the nearby canyon gorge offers stunning views and photo opportunities. Visitor numbers peak during the summer months and in October, inviting you to experience the beauty of nature and the warmth of local hospitality. - **[North Middletown:](https://www.expedia.ca/North-Middletown-Hotels.d553248634998773765.Travel-Guide-Hotels)** Located 17.7km from Winchester, North Middletown is a quaint village that combines sports, culture, and family-friendly activities. The community is home to a modern college, making it a hub for education and cultural events. Visitors can enjoy a round of golf or attend a game at the local stadium. The village features a library that serves as a community resource, and cultural events often take place throughout the year. Similar to its neighbours, North Middletown sees a rise in visitors during July to August and October, providing a welcoming atmosphere for all. ### Things to do in Winchester Winchester, Kentucky, is perfect for outdoor enthusiasts and adventure seekers alike. You can explore beautiful hiking trails, enjoy the scenic views at local recreational areas, or relax at nearby campgrounds. This charming city offers a variety of experiences that highlight its natural beauty, making it an ideal destination for a refreshing getaway. **Shopping** For a delightful shopping experience in Winchester, visit Hamburg Pavilion, located 20.9km away, featuring a variety of stores and entertainment options. If you're up for a drive, Hamburg Place, 22.5km away, offers a vibrant atmosphere perfect for family outings, while Fiber Frenzy, 48.3km away, caters to craft enthusiasts. **Recreation** Experience the serene [Southwind Golf Course](https://www.expedia.ca/Southwind-Golf-Course-Hotels.0-l6263194-0.Travel-Guide-Filter-Hotels) with its lush greens and challenging fairways, perfect for golf enthusiasts. For a unique thrill, head to [Lexington Ice Center](https://www.expedia.ca/Lexington-Ice-Center-Hotels.0-l553248621532656277-0.Travel-Guide-Filter-Hotels) 24.1km away for ice skating, combining fun with fitness. Applebee's Park, 27.4km from Winchester, offers vibrant sports events to enjoy. **Adventure** [Legacy Trail](https://www.expedia.ca/Legacy-Trail-Hotels.0-l553248621532656278-0.Travel-Guide-Filter-Hotels) is an invigorating hiking experience located 29.0km from Winchester. This scenic trail offers stunning outdoor views, making it perfect for adventure enthusiasts seeking to immerse themselves in nature's beauty and enjoy the fresh air of Kentucky's landscapes. **Nightlife** Experience the vibrant nightlife of Winchester by visiting the [EKU Center for the Arts](https://www.expedia.ca/EKU-Center-For-The-Arts-Hotels.0-l553248621587339559-0.Travel-Guide-Filter-Hotels) for a captivating performance, or catch a film at the Kentucky Theater for a cozy movie night. For a unique experience, explore the [Hummel Planetarium](https://www.expedia.ca/Hummel-Planetarium-Hotels.0-l6292844-0.Travel-Guide-Filter-Hotels), perfect for families and entertainment seekers alike. ### Booking tips and Expedia advantages for Winchester Winchester, Kentucky offers many budget-friendly options for visitors. Enjoy free attractions like Grimes Mill Winery, and save on transportation by using local buses or carpooling. To find the best deals, plan your trip between December and February, when accommodation prices drop significantly, especially on Mondays. Use Expedia to compare hotel rates and consider booking a package that combines flights and activities for added savings. By arranging your search from lowest to highest price, you can discover affordable hotels that fit your budget. - **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay in Winchester are December to February, where the prices are slightly lower. This is in comparison to April to May and October, where prices are slightly higher. - **The most and least expensive days on average to stay in a hotel:** The least expensive day to stay in Winchester is Monday. The most expensive day to stay in Winchester is Saturday. - **Find cheap hotels on Expedia:** Utilize Expedia's search tool to refine your choices based on your budget, desired location, and preferred hotel type. To discover the best prices and deals, simply arrange the price filter from lowest to highest. - **Consider bundling your trip:** You can save some money by combining your hotel stay in Winchester with your flights and activities by booking a package through Expedia. ### Find the best attractions in Winchester Winchester, Kentucky, is an ideal destination for those who enjoy outdoor adventures and stunning scenery. Visitors can explore a variety of attractions, including national and urban parks, as well as historic sites. The area offers a rich cultural experience, perfect for families and outdoor enthusiasts alike, ensuring there's something for everyone to enjoy during their stay in this charming town. - **[Fort Boonesborough State Park:](https://www.expedia.ca/Fort-Boonesborough-State-Park-Hotels.0-l6091545-0.Travel-Guide-Filter-Hotels)** Located 12.9km from Winchester, this national park offers exhilarating outdoor adventures amidst stunning scenery. Explore historical reenactments, hiking trails, and picnic areas, making it perfect for nature enthusiasts and history buffs alike. - **[Bluegrass Heritage Museum:](https://www.expedia.ca/Bluegrass-Heritage-Museum-Hotels.0-l553248621561880736-0.Travel-Guide-Filter-Hotels)** Nestled in Winchester, this museum immerses visitors in the rich culture and history of the Bluegrass region. Discover fascinating exhibits showcasing local artifacts, music, and traditions that highlight the area's unique heritage. - **[Kentucky River Museum:](https://www.expedia.ca/Kentucky-River-Museum-Hotels.0-l553248621587339561-0.Travel-Guide-Filter-Hotels)** Situated 12.9km from Winchester, this museum provides insight into the cultural significance of the Kentucky River. Engage with interactive displays and learn about the river's impact on the local community and its historical context. ### Best time to go to Winchester Visitor numbers in Winchester is generally unchanged in popularity throughout the year. The best time to visit Winchester is dependant on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly cloudy with light rain. | **![calendar icon](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature icon](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain icon](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly cloudy icon](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation rate icon](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price icon](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | --------------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------------------- | --------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------------------ | ------------------------------------------------------------------------------------------------------------------ | | January | 32.9°F (0.5°C) | Light Rain | Mostly Cloudy | Average | Slightly Low | | February | 36.9°F (2.7°C) | Light Rain | Mostly Cloudy | Average | Slightly Low | | March | 45.3°F (7.4°C) | Light Rain | Mostly Cloudy | Average | Average | | April | 54.7°F (12.6°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | May | 64.4°F (18.0°C) | Light Rain | Mostly Sunny | Average | Slightly High | | June | 72.1°F (22.3°C) | Light Rain | Mostly Sunny | Average | Average | | July | 75.4°F (24.1°C) | Light Rain | Mostly Sunny | Slightly High | Average | | August | 74.1°F (23.4°C) | Light Rain | Mostly Sunny | Average | Average | | September | 68.2°F (20.1°C) | Light Rain | Mostly Sunny | Slightly High | Average | | October | 57.0°F (13.9°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly High | | November | 45.1°F (7.3°C) | Light Rain | Mostly Sunny | Slightly Low | Average | | December | 38.8°F (3.8°C) | Light Rain | Mostly Cloudy | Slightly Low | Slightly Low | ### The nearest major airports for your trip to Winchester To reach Winchester, Kentucky, the nearest major airport is Lexington, KY ([LEX](https://www.expedia.ca/Blue-Grass-Airport-Hotels.0-aLEX-0.Travel-Guide-Filter-Hotels)\-Blue Grass), situated 37.0km away. A few excellent hotel options near the airport include [The Campbell House Lexington](https://www.expedia.ca/Lexington-Hotels-The-Campbell-House-Lexington.h27029.Hotel-Information), Curio Collection by Hilton, a 4-star hotel located 6.4km from LEX. The [Marriott Lexington Griffin Gate Golf Resort & Spa](https://www.expedia.ca/Lexington-Hotels-Lexington-Griffin-Gate-Marriott-Golf-Resort-Spa.h15892.Hotel-Information), also a 4-star resort, is 11.3km away, while the [21c Museum Hotel Lexington](https://www.expedia.ca/Lexington-Hotels-21c-Museum-Hotel-Lexington.h12243775.Hotel-Information), another 4-star establishment, is 9.7km from the airport. Transportation services are readily available from these hotels, ensuring easy access to the airport for your travel needs. ## Recent reviews of Winchester hotels ![Springhill Suites by Marriott Lexington Fritz Farm](https://images.trvl-media.com/lodging/103000000/102370000/102366200/102366172/0a801b9d_y.jpg) ### Springhill Suites by Marriott Lexington Fritz Farm 5/5 Excellent "We stay here a lot and have not had any complaints. Professional staff, great location, clean updated rooms and hot breakfast! " A verified traveller stayed at Springhill Suites by Marriott Lexington Fritz Farm Posted 2 days ago [](https://expedia.ca/Lexington-Hotels-Springhill-Suites-By-Marriott-Lexington-South.h102366172.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 5/5 Excellent "always a charming experience at the campbell house,its my favourite place and I love Kentucky " A verified traveller stayed at The Campbell House Lexington, Curio Collection by Hilton Posted 2 days ago [](https://expedia.ca/Lexington-Hotels-The-Campbell-House-Lexington.h27029.Hotel-Information) ![The Manchester ](https://images.trvl-media.com/lodging/93000000/92440000/92430600/92430541/f02815a4_y.jpg) ### The Manchester 5/5 Excellent "Great place to stay, eat and drink." A verified traveller from Nashville stayed at The Manchester Posted 2 days ago [](https://expedia.ca/Lexington-Hotels-The-Manchester.h92430541.Hotel-Information) ![21c Museum Hotel Lexington](https://images.trvl-media.com/lodging/13000000/12250000/12243800/12243775/7f6a345c_y.jpg) ### 21c Museum Hotel Lexington 5/5 Excellent "Great stay. Loved the hotel and restaurant " A verified traveller stayed at 21c Museum Hotel Lexington Posted 2 days ago [](https://expedia.ca/Lexington-Hotels-21c-Museum-Hotel-Lexington.h12243775.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 5/5 Excellent "Easy access from I 75\. Comfy beds. Will stay again." A verified traveller stayed at La Quinta Inn & Suites by Wyndham Lexington South / Hamburg Posted 4 days ago [](https://expedia.ca/Lexington-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Lexington-South-Hamburg.h283165.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 5/5 Excellent "Clean room love this place" A verified traveller stayed at DoubleTree Suites by Hilton Hotel Lexington Posted 5 days ago [](https://expedia.ca/Lexington-Hotels-DoubleTree-Suites-By-Hilton-Hotel-Lexington.h9900.Hotel-Information) ![Hilton Lexington/Downtown](https://images.trvl-media.com/lodging/1000000/10000/2200/2101/b9ab6063_y.jpg) ### Hilton Lexington/Downtown 5/5 Excellent "Nice quiet room. Staff were very helpful." A verified traveller stayed at Hilton Lexington/Downtown Posted 6 days ago [](https://expedia.ca/Lexington-Hotels-Hilton-LexingtonDowntown.h2101.Hotel-Information) ![Hyatt Regency Lexington](https://images.trvl-media.com/lodging/1000000/10000/3500/3461/c0c49295_y.jpg) ### Hyatt Regency Lexington 5/5 Excellent "Clean room. Delicious breakfast and very convenient for UK Basketball " A verified traveller stayed at Hyatt Regency Lexington Posted 6 days ago [](https://expedia.ca/Lexington-Hotels-Hyatt-Regency-Lexington.h3461.Hotel-Information) ![Elwood Hotel & Suites](https://images.trvl-media.com/lodging/3000000/2220000/2219800/2219782/f131bcc5_y.jpg) ### Elwood Hotel & Suites 5/5 Excellent "Friendly staff, clean room, easy check in and out. " A verified traveller from Oakwood stayed at Elwood Hotel & Suites Posted 6 days ago [](https://expedia.ca/Lexington-Hotels-Elwood-Hotel-Suites.h2219782.Hotel-Information) ## Frequently asked questions ### What are the best hotels in Winchester with outdoor pools? > Another solid option is the [Best Western Winchester Hotel](https://www.expedia.ca/Lexington-Hotels-Best-Western-Winchester-Hotel.h15247.Hotel-Information), featuring an outdoor pool that enhances its family-friendly appeal. Rated 8.4 by travellers, this hotel is praised for its spacious and clean rooms, friendly staff, and a great breakfast selection. With free self-parking and wired internet available, guests appreciate the thoughtful amenities that add to their overall experience. > > > For those on a budget, the [Baymont by Wyndham Winchester](https://www.expedia.ca/Lexington-Hotels-Baymont-By-Wyndham-Winchester.h422677.Hotel-Information) presents a more economical choice. Although it has a lower review score of 7.2, it still offers an outdoor pool along with free Wi-Fi and breakfast options. Guests have noted the excellent size of the rooms and the wonderful staff, making it a decent value for families looking for a fun getaway. ### How much does a hotel with outdoor pool in Winchester cost? ### Are there hotels with outdoor pools that are close to Lykins Park? > Another great option is the [Best Western Winchester Hotel](https://www.expedia.ca/Lexington-Hotels-Best-Western-Winchester-Hotel.h15247.Hotel-Information), boasting a solid review rating of 8.4\. This hotel features an inviting outdoor pool along with clean and sizable rooms. Families will particularly enjoy the hearty breakfast offerings and the friendly service provided by the staff, making it a welcoming spot for both relaxation and adventure. > > > If you're looking for a more budget-friendly choice, consider the [Baymont by Wyndham Winchester](https://www.expedia.ca/Lexington-Hotels-Baymont-By-Wyndham-Winchester.h422677.Hotel-Information). With a traveller rating of 7.2, this hotel offers an outdoor pool and convenient amenities like free WiFi and continental breakfast. Guests have noted the excellent room sizes and the wonderful service from the staff, making it a practical option for families wanting to enjoy their time near Lykins Park without breaking the bank. ### Is it cheaper to book flights and a hotel in Winchester as a package? ### How can I save on a hotel in Winchester with Expedia? ### Can I cancel my hotel reservation on Expedia? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - 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) - [Bybee Hotels ](https://www.expedia.ca/Bybee-Hotels.d553248635975865996.Travel-Guide-Hotels) - [Motels in Camargo ](https://www.expedia.ca/Camargo-Motels.d553248634998850038-aaMotels.Travel-Guide-Accommodation) - [Beach Hotel Hotels in Chevy Chase ](https://www.expedia.ca/Chevy-Chase-Lexington-Hotels-Beach-Hotel.0-n553248635976481361-0-tBeachHotel.Travel-Guide-Filter-Hotels) - 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