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) ![Lodging Image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.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=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&amenities=POOL) 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=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&amenities=PETS) 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=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&travelerType=family_friendly) 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=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&amenities=HOT_TUB) 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=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&lodging=CABIN) 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=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&lodging=AGRITOURISM) 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=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&lodging=COTTAGE) 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=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&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=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&lodging=CONDO) ## Check prices for these dates Tonight [Feb 26 - Feb 27](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-02-26&endDate=2026-02-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 27 - Feb 28](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-02-27&endDate=2026-02-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-02-27&endDate=2026-03-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-03-06&endDate=2026-03-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester hotels ![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) ![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) ![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 $99 CA $109 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Lexington-Hotels-Comfort-Inn.h327866.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/c7af9b8d.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) ### 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 $110 CA $122 total includes taxes & fees Mar 9 - Mar 10 [](https://www.expedia.ca/Lexington-Hotels-Baymont-By-Wyndham-Winchester.h422677.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 (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 1 - Mar 2 [](https://www.expedia.ca/Lexington-Hotels-Red-Roof-Inn-Lexington-Winchester.h5872.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/15300/15247/w5755h3835x5y5-d8ce41cd.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) ### 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 $104 CA $115 total includes taxes & fees Mar 2 - Mar 3 [](https://www.expedia.ca/Lexington-Hotels-Best-Western-Winchester-Hotel.h15247.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/25000000/24370000/24362600/24362582/407ca96d.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 9.2/10 Wonderful (546 reviews) "Clean room, great hot fresh breakfast " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bob CA $130 CA $144 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Lexington-Hotels-Holiday-Inn-Express-Lexington-East-Winchester.h24362582.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) ![Lobby](https://images.trvl-media.com/lodging/109000000/108680000/108675700/108675613/d19dbf75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/109000000/108680000/108675700/108675613/489887ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/109000000/108680000/108675700/108675613/812dcf31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Value Stay [](https://www.expedia.ca/Lexington-Hotels-Value-Stay.h108675613.Hotel-Information) Winchester 7.8/10 Good (128 reviews) "Awesome rooms and service" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brandon CA $81 CA $89 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Lexington-Hotels-Value-Stay.h108675613.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) ![Room, Accessible, Non Smoking](https://images.trvl-media.com/lodging/1000000/20000/16300/16227/83fc2e38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Winchester [](https://www.expedia.ca/Lexington-Hotels-Hampton-Inn-Winchester.h16227.Hotel-Information) Winchester 9.2/10 Wonderful (456 reviews) "Would stay there again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patricia CA $165 CA $182 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Lexington-Hotels-Hampton-Inn-Winchester.h16227.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) ![Porch](https://images.trvl-media.com/lodging/28000000/27530000/27529500/27529446/9c5ead39.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) ![BBQ/picnic area](https://images.trvl-media.com/lodging/28000000/27530000/27529500/27529446/cbc3315c.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 (493 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 $176 CA $194 total includes taxes & fees Feb 27 - Feb 28 [](https://www.expedia.ca/Wilmore-Hotels-Asbury-Inn-Suites.h27529446.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 | Terrace/patio](https://images.trvl-media.com/lodging/16000000/15440000/15437800/15437778/278782c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/16000000/15440000/15437800/15437778/ebd7e3b5.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 (1,807 reviews) "Great setting and very convenient to everything. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) WILLIAM [](https://www.expedia.ca/Slade-Hotels-Natural-Bridge-State-Resort-Park.h15437778.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/12000000/11860000/11855100/11855099/800aa1cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/12000000/11860000/11855100/11855099/65bd90f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/12000000/11860000/11855100/11855099/a188c789.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Double Beds](https://images.trvl-media.com/lodging/12000000/11860000/11855100/11855099/08288a3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Black Bear Lodge Motel [](https://www.expedia.ca/Slade-Hotels-Black-Bear-Lodge-Motel.h11855099.Hotel-Information) Slade 8.0/10 Very good (639 reviews) "Really great place to stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Barbara CA $120 CA $133 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Slade-Hotels-Black-Bear-Lodge-Motel.h11855099.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/7000000/6650000/6648900/6648831/816f55e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, free cribs/infant beds, rollaway beds](https://images.trvl-media.com/lodging/7000000/6650000/6648900/6648831/cf0457d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/7000000/6650000/6648900/6648831/13bd4e68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, free cribs/infant beds, rollaway beds](https://images.trvl-media.com/lodging/7000000/6650000/6648900/6648831/1ec61e3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn Lexington South [](https://www.expedia.ca/Lexington-Hotels-Comfort-Inn-Lexington-South.h6648831.Hotel-Information) Nicholasville 8.2/10 Very good (623 reviews) "Room was spotless, staff was very curtious. Great breakfast, great place to stay when passing through. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tammy CA $97 CA $107 total includes taxes & fees Mar 15 - Mar 16 [](https://www.expedia.ca/Lexington-Hotels-Comfort-Inn-Lexington-South.h6648831.Hotel-Information) ![Daily to-go breakfast for a fee](https://images.trvl-media.com/lodging/2000000/1680000/1674700/1674666/ccab00ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1680000/1674700/1674666/0527535e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1680000/1674700/1674666/1b562913.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1680000/1674700/1674666/507e7370.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Lexington Georgetown [](https://www.expedia.ca/Lexington-Hotels-Hilton-Garden-Inn-Lexington-Georgetown.h1674666.Hotel-Information) Georgetown 8.8/10 Excellent (868 reviews) "The front desk girl was very nice and helpful. So was the bartender. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew CA $137 CA $151 total includes taxes & fees Mar 6 - Mar 7 [](https://www.expedia.ca/Lexington-Hotels-Hilton-Garden-Inn-Lexington-Georgetown.h1674666.Hotel-Information) ![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/50000/42500/42455/8d6292d6.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) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/50000/42500/42455/74e92478.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) ### 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 (722 reviews) "We stay here anytime we are in town " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Donn CA $108 CA $119 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Mount-Sterling-Hotels-Comfort-Inn-And-Suites.h42455.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/430000/424300/424216/a4ab22f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/430000/424300/424216/12ed63b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/430000/424300/424216/55da3f22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/1000000/430000/424300/424216/b4447817.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Nicholasville by IHG [](https://www.expedia.ca/Lexington-Hotels-Holiday-Inn-Express-Nicholasville.h424216.Hotel-Information) Nicholasville 8.8/10 Excellent (612 reviews) "Yes, staff was great, the room was clean and very comfortable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) scott G CA $124 CA $137 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Lexington-Hotels-Holiday-Inn-Express-Nicholasville.h424216.Hotel-Information) ![In-room safe, desk, laptop workspace, iron/ironing board](https://images.trvl-media.com/lodging/1000000/70000/68000/67968/e0257433.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/70000/68000/67968/dedb0544.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/70000/68000/67968/eb050f9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/70000/68000/67968/94365bfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Lexington/Georgetown [](https://www.expedia.ca/Lexington-Hotels-Hampton-Inn-Lexington-Georgetown-I-75.h67968.Hotel-Information) Georgetown 8.6/10 Excellent (502 reviews) "Enjoyed the stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Travis CA $125 CA $138 total includes taxes & fees Mar 27 - Mar 28 [](https://www.expedia.ca/Lexington-Hotels-Hampton-Inn-Lexington-Georgetown-I-75.h67968.Hotel-Information) ![Hypo-allergenic bedding, pillowtop beds, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/310000/304900/304814/c3cb7569.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/310000/304900/304814/fd7ddeff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/310000/304900/304814/3041c038.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/310000/304900/304814/e1f479f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Microtel Inn by Wyndham Georgetown [](https://www.expedia.ca/Lexington-Hotels-Microtel-Inn-By-Wyndham-Georgetown.h304814.Hotel-Information) Georgetown 7.8/10 Good (999 reviews) "Perfect place!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel CA $94 CA $104 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Lexington-Hotels-Microtel-Inn-By-Wyndham-Georgetown.h304814.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/42500/42465/1f5a8411.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/ade4d65a.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 (1,002 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 $108 CA $119 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Lexington-Hotels-Baymont-By-Wyndham-Georgetown.h42465.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/540000/532700/532630/686015f2.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) ### 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 (1,004 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 1 - Mar 2 [](https://www.expedia.ca/Lexington-Hotels-Best-Western-Plus-Georgetown-Corporate-Center-Hotel.h532630.Hotel-Information) ![Free daily full breakfast](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485603/64ceda28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485603/30f43151.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485603/594315e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485603/4709d60a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homewood Suites Lexington-Hamburg [](https://www.expedia.ca/Lexington-Hotels-Homewood-Suites-Lexington-Hamburg.h1485603.Hotel-Information) Lexington 9.2/10 Wonderful (666 reviews) "Our stay was great! All of the staff were very friendly and helpful!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carly CA $145 CA $168 total includes taxes & fees Mar 13 - Mar 14 [](https://www.expedia.ca/Lexington-Hotels-Homewood-Suites-Lexington-Hamburg.h1485603.Hotel-Information) ![Desk, iron/ironing board, free cribs/infant beds, rollaway beds](https://images.trvl-media.com/lodging/1000000/10000/9600/9539/a12e6f68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Combined shower/tub, free toiletries, towels](https://images.trvl-media.com/lodging/1000000/10000/9600/9539/910543d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/9600/9539/6b7b4c8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/9600/9539/685edbce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Days Inn Lexington SE/Hamburg [](https://www.expedia.ca/Lexington-Hotels-Days-Inn-By-Wyndham-Lexington-Southeast.h9539.Hotel-Information) Lexington 7.2/10 Good (1,004 reviews) "Staff was very friendly, room was clean. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth CA $77 CA $89 total includes taxes & fees Mar 15 - Mar 16 [](https://www.expedia.ca/Lexington-Hotels-Days-Inn-By-Wyndham-Lexington-Southeast.h9539.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=2026-03-12&endDate=2026-03-13®ionId=7876&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=HTG_SPRING_PROMO_7876) ![](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) ## Stay near popular Winchester attractions ### Winchester Traveling Trail Explore the great outdoors at Winchester Traveling Trail, a lovely green space in Winchester. You can enjoy the restaurants while in the area. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=927864477838307328) ### Bluegrass Heritage Museum You can spend time browsing the exhibits at Bluegrass Heritage Museum during your trip to Winchester. While you're here, you can savor the top-notch restaurants. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621561880736) ### Southwind Golf Course Enjoy a round of golf in Winchester at Southwind Golf Course. While in this family-friendly area, you can savor the top-notch restaurants. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6263194) ### Lykins Park 3.3/5 (4 reviews) Explore the great outdoors at Lykins Park, a lovely green space in Winchester. While in this family-friendly area, you can enjoy the restaurants. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6263146) ### College Park Explore the great outdoors at College Park, a lovely green space in Winchester. You can enjoy the restaurants while in the area. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=927864620207947776) ### Cassell Creek Golf Course Play a round of golf in Winchester at Cassell Creek Golf Course, and enjoy other activities such as horseback riding. Savor the charming coffeehouses and top-notch restaurants while in town. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6263137) ### Community Park Explore the great outdoors at Community Park, a lovely green space in Winchester. While in this family-friendly area, you can savor the top-notch restaurants. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6263168) ### Wiseman Park Explore the great outdoors at Wiseman Park, a lovely green space in Winchester. You can enjoy the restaurants while in the area. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=927864474891808768) ## 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=2026-03-12&endDate=2026-03-13&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 ## Top Winchester Hotel Reviews ## Recent Reviews in Winchester ![Home2 Suites by Hilton Lexington Hamburg](https://images.trvl-media.com/lodging/58000000/57490000/57487400/57487334/f62e7bf5_y.jpg) ### Home2 Suites by Hilton Lexington Hamburg 10/10 Excellent "Everything was great" [](https://expedia.ca/Panacea-Hotels-Home2-Suites-By-Hilton-Lexington-Hamburg.h57487334.Hotel-Information) ![The Manchester ](https://images.trvl-media.com/lodging/93000000/92440000/92430600/92430541/f02815a4_y.jpg) ### The Manchester 10/10 Excellent "Great experience!" [](https://expedia.ca/Lexington-Hotels-The-Manchester.h92430541.Hotel-Information) ![Candlewood Suites Lexington Medical District by IHG](https://images.trvl-media.com/lodging/69000000/68050000/68049000/68048979/9303a1c8_y.jpg) ### Candlewood Suites Lexington Medical District by IHG 10/10 Excellent "The room was very clean and spacious, we only stayed for a short time but I enjoyed the room and felt safe. The staff was very nice when my partner went down to buy snacks. We would definitely stay again!" [](https://expedia.ca/Lexington-Hotels-Candlewood-Suites-Lexington-Medical-District.h68048979.Hotel-Information) ![Holiday Inn Lexington - Hamburg by IHG](https://images.trvl-media.com/lodging/23000000/22760000/22757700/22757695/776ae294_y.jpg) ### Holiday Inn Lexington - Hamburg by IHG 10/10 Excellent "Everything was great " [](https://expedia.ca/Lexington-Hotels-Holiday-Inn-Lexington-Hamburg.h22757695.Hotel-Information) ![21c Museum Hotel Lexington](https://images.trvl-media.com/lodging/13000000/12250000/12243800/12243775/7f6a345c_y.jpg) ### 21c Museum Hotel Lexington 10/10 Excellent "Provided non down pillows. Got us in early. Very accommodating." [](https://expedia.ca/Lexington-Hotels-21c-Museum-Hotel-Lexington.h12243775.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) ![The Campbell House Lexington, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/30000/27100/27029/2fd2c43b_y.jpg) ### The Campbell House Lexington, Curio Collection by Hilton 10/10 Excellent "Very lovely!" [](https://expedia.ca/Lexington-Hotels-The-Campbell-House-Lexington.h27029.Hotel-Information) ![Quality Inn Lexington -Horse Park](https://images.trvl-media.com/lodging/1000000/30000/22700/22656/6339efc4_y.jpg) ### Quality Inn Lexington -Horse Park 10/10 Excellent "Nice clean rooms, quiet during the night. I would go back again" [](https://expedia.ca/Lexington-Hotels-Quality-Inn-Lexington.h22656.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 "Nice room. Very courteous staff" [](https://expedia.ca/Lexington-Hotels-Fairfield-Inn-Suites-By-Marriott-Lexington-North.h2803646.Hotel-Information) ## More cheap stays in Winchester ![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 $77 CA $89 total Mar 15 - Mar 16 includes taxes & fees 7.2/10 Good! (1,004 reviews) [](https://expedia.ca/Lexington-Hotels-Days-Inn-By-Wyndham-Lexington-Southeast.h9539.Hotel-Information) ![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 $87 CA $95 total Feb 28 - Mar 1 includes taxes & fees 8.4/10 Very Good! (1,000 reviews) [](https://expedia.ca/Lexington-Hotels-Super-8-By-Wyndham-Georgetown.h459849.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 $88 CA $102 total Mar 15 - Mar 16 includes taxes & fees 8.2/10 Very Good! (1,630 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 $98 CA $113 total Mar 1 - Mar 2 includes taxes & fees 8.4/10 Very Good! (1,544 reviews) [](https://expedia.ca/Lexington-Hotels-GuestHouse-Lexington.h426325.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 $136 CA $157 total Mar 8 - Mar 9 includes taxes & fees 9.4/10 Exceptional! (469 reviews) [](https://expedia.ca/Lexington-Hotels-Everhome-Suites-Lexington-North.h101171857.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 $137 CA $159 total Mar 29 - Mar 30 includes taxes & fees 9.4/10 Exceptional! (586 reviews) [](https://expedia.ca/Lexington-Hotels-Tru-By-Hilton-Lexington-University-Medical-Center.h78004839.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. ## Frequently asked questions ### What is the best area to stay in Winchester? > This neighbourhood is the heart of Winchester, offering a blend of historic charm and convenient access to local attractions. You'll find many of the city's independent shops, restaurants, and cafes concentrated along these main thoroughfares. The area is quite walkable, making it easy to explore on foot. > > > For couples looking for a relaxed getaway, downtown Winchester is an excellent choice. You can enjoy strolls through the historic streets, dine at local eateries, and visit attractions like the Bluegrass Heritage Museum or the Old Courthouse. Many of the boutique accommodations are also found here. > > > Visitors interested in exploring the local culture and history will find downtown Winchester particularly appealing. ### What are the best hotels in Winchester that travellers recommend? > The Hampton Inn Winchester is a highly-rated option with a 9.2 review score. Guests frequently praise the friendly and helpful staff, the clean and great rooms, and the convenient parking. The hotel offers complimentary breakfast, including a buffet, and amenities like deep-soaking bathtubs and the option for connecting rooms. It is also conveniently located near Community Park and Lykins Park. > > > Another excellent choice is the Holiday Inn Express Lexington East - Winchester by IHG, also boasting a 9.2 rating. Travellers appreciate the friendly and professional staff, the comfortable and clean rooms, and the great breakfast, which includes a buffet. The hotel features an indoor pool and 24-hour fitness facilities. ### What are the best family hotels in Winchester? > The Hampton Inn Winchester, with a 9.2 rating, offers complimentary breakfast, free WiFi, and free self-parking. It provides amenities such as rollaway extra beds and free cribs, and connecting rooms are available, making it very convenient for families. It is also well-located near Community Park and Lykins Park. Guests frequently mention the friendly and helpful staff and the clean rooms. > > > Another good option is the 3-star Best Western Winchester Hotel, rated 8.4\. This hotel features a pool, free breakfast, and free self-parking. Connecting rooms are also available. It is close to Community Park, Wiseman Park, and GRCHS Baseball Field. Guests often praise the clean and spacious rooms, the friendly staff, and the great breakfast. > > > The Holiday Inn Express Lexington East - Winchester by IHG, with a 9.2 rating, provides free cribs and connecting rooms, as well as a pool and complimentary buffet breakfast. Guests appreciate the friendly and professional staff and the comfortable, clean rooms. Find more [child-friendly accommodations in Winchester](https://www.expedia.ca/Winchester-Hotels-Family-Hotel.0-0-d7876-tFamilyHotel.Travel-Guide-Filter-Hotels) ### What hotels in Winchester offer free breakfast? > The 9.2-rated Holiday Inn Express Lexington East - Winchester by IHG provides a complimentary buffet breakfast and free WiFi. Guests frequently mention the friendly and professional staff, as well as the comfortable and clean rooms. A nice fitness centre is also available. > > > Another excellent choice is the 9.2-rated Hampton Inn Winchester, which also offers a free buffet breakfast and free WiFi. It is conveniently located near Community Park (1.8 km) and Lykins Park (1.3 km). Guests appreciate the clean rooms and helpful staff. > > > The 8.4-rated Best Western Winchester Hotel features a complimentary full breakfast and free wired internet. Guests often highlight the clean and spacious rooms, as well as the friendly staff. It is situated close to Community Park (1.3 km) and Wiseman Park (1.1 km). > > > The Baymont by Wyndham Winchester, rated 7.2, provides a free continental breakfast and free WiFi. Travellers frequently comment on the excellent and spacious rooms, as well as the wonderful staff. It is located near Community Park (1.7 km) and Lykins Park (1.4 km). Find more [hotels with free breakfast in Winchester](https://www.expedia.ca/Winchester-Hotels-Hotels-With-Free-Breakfast.0-0-d7876-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels) ### What are the top pet-friendly hotels in Winchester? > The 3-star Hampton Inn Winchester, with a 9.2 rating, welcomes both dogs and cats. Guests frequently praise the friendly and helpful staff, the clean and great rooms, and the convenient parking. A complimentary buffet breakfast is available, and free Wi-Fi is provided. It's located near Community Park and Lykins Park. > > > Another excellent choice is the 3-star Best Western Winchester Hotel, rated 8.4, which also permits pets. Guests often comment on the clean and big rooms, the friendly and nice staff, and the great breakfast. The hotel is close to Community Park, Wiseman Park, and GRCHS Baseball Field. See more [pet-friendly hotels in Winchester](https://www.expedia.ca/Winchester-Hotels-Pet-Friendly-Hotel.0-0-d7876-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) ### What are the best budget hotels in Winchester? > The Hampton Inn Winchester, with a 9.2 rating, provides complimentary breakfast and free WiFi, along with free toiletries and convenient free self-parking. Guests frequently praise the friendly and helpful staff, the clean and great rooms, and its good location. It is also close to Community Park, just 1.8 km away. > > > Another highly-rated option is the Holiday Inn Express Lexington East - Winchester by IHG, also with a 9.2 rating. This hotel offers complimentary breakfast, including a buffet, free toiletries, and free self-parking, as well as free WiFi. Reviewers often highlight the friendly and professional staff, the comfortable and clean rooms, and the great breakfast. View all [budget hotels in Winchester](https://www.expedia.ca/Winchester-Hotels-Cheap-Hotels.0-0-d7876-tCheapHotels.Travel-Guide-Filter-Hotels) ### What are the best hotels in Winchester near Lykins Park? > The Baymont by Wyndham Winchester, with a 7.2 rating, is a good option as it is located just 1.4 km from Lykins Park. Guests frequently mention the excellent and big rooms, and the wonderful staff. It offers a complimentary continental breakfast, free internet, and a pool. > > > Another choice is the Red Roof Inn Winchester - Lexington East, which is also conveniently located just 1.3 km from Lykins Park. This hotel provides free WiFi and free parking for cars, RVs, buses, and trucks. Guests appreciate the complimentary coffee available. ### When is the best time to go to Winchester? > In spring, you'll find comfortable temperatures, typically ranging from 10°C to 20°C, making it ideal for outdoor activities like visiting local horse farms or exploring the natural beauty of the Red River Gorge, which is a short drive away. The countryside is lush, and many local attractions begin their extended operating hours. > > > Autumn also provides agreeable weather, with temperatures usually between 10°C and 22°C. The changing leaves in the surrounding hills create a picturesque backdrop, great for scenic drives through the Bourbon Trail or enjoying a relaxed afternoon at a local vineyard. This season often coincides with various local festivals and events, offering a chance to experience the community spirit. > > > While summer (June to August) can be warm and humid, with temperatures often exceeding 28°C, it's still a popular time for visitors, particularly for those interested in water activities or attending outdoor concerts. ### Can I cancel my hotel reservation on Expedia? ### How can I save on a Winchester hotel booking with Expedia? ### How much is the nightly rate at a Winchester hotel? ## 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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