Title: Book the Best Winchester LUXURY Hotels - Upscale Hotels in Winchester, KY | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d7876.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d7876.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d7876.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d7876.Destination-Travel-Guides) ![Thanks to my friend of mine who's recommended me to this spot easy hike short walk to get there ](https://images.trvl-media.com/place/7876/9403688e-dbbb-4255-9528-8bddb2ed4db3.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Nawa Aseen # Find luxury hotels in Winchester, KY - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Winchester Luxury Hotels Tonight [Dec 18 - Dec 19](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2025-12-18&endDate=2025-12-19&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Dec 19 - Dec 20](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2025-12-19&endDate=2025-12-20&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) This weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2025-12-19&endDate=2025-12-21&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2025-12-26&endDate=2025-12-28&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Our top choices for Winchester luxury hotels ![Exterior detail](https://images.trvl-media.com/lodging/3000000/2220000/2219800/2219782/f131bcc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite, Multiple Beds (Family Two Room Suite King / 2 Twins)](https://images.trvl-media.com/lodging/3000000/2220000/2219800/2219782/ae374418.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2220000/2219800/2219782/630a1adf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/3000000/2220000/2219800/2219782/0ca9b5f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Elwood Hotel & Suites [](https://www.expedia.ca/Lexington-Hotels-Elwood-Hotel-Suites.h2219782.Hotel-Information) Lexington 9.4/10 Exceptional (1003) "We would stay there again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $139 CA $162 total includes taxes & fees Dec 26 - Dec 27 [](https://www.expedia.ca/Lexington-Hotels-Elwood-Hotel-Suites.h2219782.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/20000/15900/15892/79f835ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/20000/15900/15892/3264e39f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/15900/15892/w3996h2667x0y0-d59531f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/15900/15892/d4592337.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Marriott Lexington Griffin Gate Golf Resort & Spa [](https://www.expedia.ca/Lexington-Hotels-Lexington-Griffin-Gate-Marriott-Golf-Resort-Spa.h15892.Hotel-Information) Lexington 8.6/10 Excellent (587) "Quick stay, very clean, nice staff!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patrick CA $131 CA $180 total includes taxes & fees Jan 19 - Jan 20, 2026 [](https://www.expedia.ca/Lexington-Hotels-Lexington-Griffin-Gate-Marriott-Golf-Resort-Spa.h15892.Hotel-Information) ![Breakfast and dinner served](https://images.trvl-media.com/lodging/1000000/10000/9900/9900/a13e8efc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Two Room Suite, 1 King Bed with Sofa Bed, Balcony Interior View](https://images.trvl-media.com/lodging/1000000/10000/9900/9900/d29ff7ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/9900/9900/1835b946.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/9900/9900/87def9e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree Suites by Hilton Hotel Lexington [](https://www.expedia.ca/Lexington-Hotels-DoubleTree-Suites-By-Hilton-Hotel-Lexington.h9900.Hotel-Information) Lexington 8.8/10 Excellent (1014) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $123 CA $143 total includes taxes & fees Dec 25 - Dec 26 [](https://www.expedia.ca/Lexington-Hotels-DoubleTree-Suites-By-Hilton-Hotel-Lexington.h9900.Hotel-Information) ![Interior entrance](https://images.trvl-media.com/lodging/93000000/92440000/92430600/92430541/e4c398a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop terrace](https://images.trvl-media.com/lodging/93000000/92440000/92430600/92430541/0e7a8ca2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Penthouse (The Penthouse Suite)](https://images.trvl-media.com/lodging/93000000/92440000/92430600/92430541/29dadabc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/93000000/92440000/92430600/92430541/d2509ef5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Manchester [](https://www.expedia.ca/Lexington-Hotels-The-Manchester.h92430541.Hotel-Information) Distillery District 9.6/10 Exceptional (1084) "Great place, highly recommend!! Staff was great, food was aweseome!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrew CA $211 CA $269 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Lexington-Hotels-The-Manchester.h92430541.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/13000000/12250000/12243800/12243775/653cb913.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast and dinner served](https://images.trvl-media.com/lodging/13000000/12250000/12243800/12243775/df7c3e61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/13000000/12250000/12243800/12243775/0b04e16b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/13000000/12250000/12243800/12243775/51aa8887.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 21c Museum Hotel Lexington [](https://www.expedia.ca/Lexington-Hotels-21c-Museum-Hotel-Lexington.h12243775.Hotel-Information) Downtown Lexington 8.8/10 Excellent (1000) "Great hotel and location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tammy CA $186 CA $223 total includes taxes & fees Jan 10 - Jan 11, 2026 [](https://www.expedia.ca/Lexington-Hotels-21c-Museum-Hotel-Lexington.h12243775.Hotel-Information) ![Serves dinner and happy hour](https://images.trvl-media.com/lodging/1000000/30000/27100/27029/68f1f7a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; southern cuisine ](https://images.trvl-media.com/lodging/1000000/30000/27100/27029/fb6ce1b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/27100/27029/ceff0725.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/30000/27100/27029/151a7ae4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Campbell House Lexington, Curio Collection by Hilton [](https://www.expedia.ca/Lexington-Hotels-The-Campbell-House-Lexington.h27029.Hotel-Information) Lexington 8.2/10 Very good (1000) "Room was nice and front desk folks were warm and courteous. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Keith CA $129 CA $150 total includes taxes & fees Dec 25 - Dec 26 [](https://www.expedia.ca/Lexington-Hotels-The-Campbell-House-Lexington.h27029.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=2026-01-02&endDate=2026-01-03®ionId=7876&adults=2&sort=LUXURY&star=40,50&openPlayBack=true) ## Top Winchester Hotel Reviews ![Spark by Hilton Lexington Hamburg](https://images.trvl-media.com/lodging/1000000/10000/6700/6639/4dbc3493_y.jpg) ### Spark by Hilton Lexington Hamburg 10/10 Excellent "Needs protein added to the breakfast bar. Most hotels are serving eggs and bacon even as a free continental breakfast. I expect that from a Hilton hotel. " [](https://expedia.ca/Lexington-Hotels-Spark-By-Hilton-Lexington-Hamburg.h6639.Hotel-Information) ![Marriott Lexington Griffin Gate Golf Resort & Spa](https://images.trvl-media.com/lodging/1000000/20000/15900/15892/79f835ef_y.jpg) ### Marriott Lexington Griffin Gate Golf Resort & Spa 10/10 Excellent "The room was very clean and her a great staff everyone was so helpful. The valet cleaned the snow and ice off our vehicle and we were not even in valet parking did not get to get his name but he went above and beyond. " [](https://expedia.ca/Lexington-Hotels-Lexington-Griffin-Gate-Marriott-Golf-Resort-Spa.h15892.Hotel-Information) ![GuestHouse Lexington](https://images.trvl-media.com/lodging/1000000/430000/426400/426325/18dc9903_y.jpg) ### GuestHouse Lexington 10/10 Excellent "Efficient. Convenient location. " [](https://expedia.ca/Lexington-Hotels-GuestHouse-Lexington.h426325.Hotel-Information) ![Embassy Suites by Hilton Lexington/UK Coldstream](https://images.trvl-media.com/lodging/1000000/210000/203600/203587/32ffb492_y.jpg) ### Embassy Suites by Hilton Lexington/UK Coldstream 10/10 Excellent "The lady at the front desk was a sweetheart. As our attempt to check in early failed only because the room wasn’t ready yet, she gave us directions and restaurant ideas so we could have a nice meal and drinks before the game. The room was clean and inviting. The complementary drinks and great breakfast was a plus!! " [](https://expedia.ca/Lexington-Hotels-Embassy-Suites-By-Hilton-LexingtonUK-Coldstream.h203587.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 "Staff was very nice and process was quick " [](https://expedia.ca/Lexington-Hotels-DoubleTree-Suites-By-Hilton-Hotel-Lexington.h9900.Hotel-Information) ![Elwood Hotel & Suites](https://images.trvl-media.com/lodging/3000000/2220000/2219800/2219782/f131bcc5_y.jpg) ### Elwood Hotel & Suites 10/10 Excellent "We would stay there again" [](https://expedia.ca/Lexington-Hotels-Elwood-Hotel-Suites.h2219782.Hotel-Information) ![Motel 6 Lexington, KY - Airport](https://images.trvl-media.com/lodging/1000000/20000/18500/18423/0a65cd84_y.jpg) ### Motel 6 Lexington, KY - Airport 10/10 Excellent "Great place to stay." [](https://expedia.ca/Lexington-Hotels-Motel-6-Lexington.h18423.Hotel-Information) ![Best Western Winchester Hotel](https://images.trvl-media.com/lodging/1000000/20000/15300/15247/690f0ff1_y.jpg) ### Best Western Winchester Hotel 10/10 Excellent "This is our 2nd time staying here. Convenient stop on our trip. Rooms are clean and well maintained. The night check in guy Jared was very friendly & helpful. " [](https://expedia.ca/Lexington-Hotels-Best-Western-Winchester-Hotel.h15247.Hotel-Information) ## Frequently asked questions ### Which area of Winchester is best to stay in for luxury hotels? > This area is primarily known for its modern conveniences and easy access. It's characterised by newer developments, including a selection of well-appointed hotels, a variety of dining options, and retail parks. While not in the historic centre, its proximity to the interstate makes it a convenient base for exploring the wider region. > > > Couples looking for a comfortable and stress-free stay will appreciate the amenities often found in hotels here, such as high-end fitness equipment, indoor swimming pools, and spacious rooms. It's a great option for those who plan to explore the Bourbon Trail or nearby equine attractions, as it offers straightforward access to major routes. > > > For those travelling for business, the hotels in this area provide modern facilities and good connectivity, making it easy to commute to local businesses or attend conferences. ### How much does a luxury hotel in Winchester cost? ### What luxury activities and experiences are there in Winchester? > For those interested in the equine world, private tours of renowned thoroughbred horse farms offer an exclusive look into the breeding and training of champion racehorses. These experiences often include meeting the horses up close and learning about their lineage directly from experienced handlers. This is particularly appealing to couples or small groups who appreciate bespoke encounters and the heritage of horse racing. > > > Bourbon enthusiasts can enjoy curated distillery tours, which often include private tastings of rare or limited-edition bourbons. Some distilleries offer behind-the-scenes access to their rickhouses and production facilities, guided by master distillers. These tours provide a deeper understanding of the bourbon-making process and an opportunity to acquire unique bottles. This experience is well-suited for connoisseurs and those looking for a sophisticated tasting adventure. > > > Winchester also boasts several farm-to-table restaurants that provide an elevated dining experience. These establishments frequently source ingredients from local farms, offering seasonal menus that highlight the region's agricultural bounty. Many also feature extensive wine lists and craft cocktails, providing a refined setting for a special evening out. ### How can I save on a luxury hotel in Winchester with Expedia? ### Is it cheaper to book a luxury Winchester hotel and flights as a package? ### Can I cancel my luxury hotel reservation on Expedia? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [Hotels near Applebee s Park ](https://www.expedia.ca/Applebee-S-Park-Hotels.0-l553248621557921127-0.Travel-Guide-Filter-Hotels) - [Motels in Camargo ](https://www.expedia.ca/Camargo-Motels.d553248634998850038-aaMotels.Travel-Guide-Accommodation) - [Chevy Chase Hotels ](https://www.expedia.ca/Chevy-Chase-Lexington-Hotels.0-n553248635976481361-0.Travel-Guide-Filter-Hotels) - [Hotels near Claiborne Farm ](https://www.expedia.ca/Claiborne-Farm-Hotels.0-l553248621559866398-0.Travel-Guide-Filter-Hotels) - [Cabin Rentals in Clay City ](https://www.expedia.ca/Clay-City-Cabins.d3000438412-aaCabins.Travel-Guide-Accommodation) - 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