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) ![](https://mediaim.expedia.com/destination/2/2d4532767bd47b707b21acca86317ffc.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Hyelsinta # 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 [Oct 31 - Nov 1](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2025-10-31&endDate=2025-11-01&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Nov 1 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2025-11-01&endDate=2025-11-02&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2025-10-31&endDate=2025-11-02&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2025-11-07&endDate=2025-11-09&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Top Winchester Luxury Hotels ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/20000/15300/15247/690f0ff1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/15300/15247/80f943aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/15300/15247/2ea0f039.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room amenity](https://images.trvl-media.com/lodging/1000000/20000/15300/15247/6f58ef98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Winchester Hotel Winchester 8.4/10 Very good (992) "A good value for an overnight stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert N CA $113 CA $124 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Lexington-Hotels-Best-Western-Winchester-Hotel.h15247.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-15&endDate=2025-11-16®ionId=7876&adults=2&star=50&sort=RECOMMENDED&openPlayBack=true) ## Top Winchester Hotel Reviews ![Embassy Suites by Hilton Lexington/UK Coldstream](//images.trvl-media.com/lodging/1000000/210000/203600/203587/32ffb492_y.jpg) ### Embassy Suites by Hilton Lexington/UK Coldstream 10/10 Excellent "Terrific staff, room was a good location and comfortable bed. Very good breakfast also. Omelette was amazing! " [](https://expedia.ca/Lexington-Hotels-Embassy-Suites-By-Hilton-LexingtonUK-Coldstream.h203587.Hotel-Information) ![Elwood Hotel & Suites](//images.trvl-media.com/lodging/3000000/2220000/2219800/2219782/f131bcc5_y.jpg) ### Elwood Hotel & Suites 10/10 Excellent "Cute room and hotel. We will stay again. " [](https://expedia.ca/Lexington-Hotels-Elwood-Hotel-Suites.h2219782.Hotel-Information) ![Hyatt Place Lexington](//images.trvl-media.com/lodging/3000000/2060000/2057700/2057644/91e06cc9_y.jpg) ### Hyatt Place Lexington 10/10 Excellent "Clean room" [](https://expedia.ca/Lexington-Hotels-Hyatt-Place-Lexington.h2057644.Hotel-Information) ![Spark by Hilton Lexington Hamburg](//images.trvl-media.com/lodging/1000000/10000/6700/6639/4dbc3493_y.jpg) ### Spark by Hilton Lexington Hamburg 10/10 Excellent "Very clean in all respects. Comfortable bed. Great value." [](https://expedia.ca/Lexington-Hotels-Spark-By-Hilton-Lexington-Hamburg.h6639.Hotel-Information) ![Motel 6 Lexington, KY - Airport](//images.trvl-media.com/lodging/1000000/20000/18500/18423/0a65cd84_y.jpg) ### Motel 6 Lexington, KY - Airport 8/10 Good "Room has been pretty decent " [](https://expedia.ca/Lexington-Hotels-Motel-6-Lexington.h18423.Hotel-Information) ![Motel 6 Lexington, KY - East I-75](//images.trvl-media.com/lodging/2000000/1040000/1039800/1039703/c1f9e9cf_y.jpg) ### Motel 6 Lexington, KY - East I-75 10/10 Excellent "the room itself was okay but there were little things like stink bugs and flies around the room " [](https://expedia.ca/Lexington-Hotels-Motel-6-Lexington.h1039703.Hotel-Information) ![GuestHouse Lexington](//images.trvl-media.com/lodging/1000000/430000/426400/426325/18dc9903_y.jpg) ### GuestHouse Lexington 10/10 Excellent "Very quiet location, clean room, guest quiet and respectful. Different from other chain hotels (guests quiet and respectful)" [](https://expedia.ca/Lexington-Hotels-GuestHouse-Lexington.h426325.Hotel-Information) ![Comfort Inn & Suites](//images.trvl-media.com/lodging/1000000/30000/27400/27364/25d8ec98_y.jpg) ### Comfort Inn & Suites 10/10 Excellent "Loved it" [](https://expedia.ca/Lexington-Hotels-Comfort-Inn-Suites.h27364.Hotel-Information) ![Best Western Winchester Hotel](//images.trvl-media.com/lodging/1000000/20000/15300/15247/690f0ff1_y.jpg) ### Best Western Winchester Hotel 10/10 Excellent "It was a great choice for us. Super clean. All the space we needed. Our car was conveniently parked outside our room door. Breakfast was a nice touch too." [](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? > The best area to stay in Winchester for luxury hotels is along the Winchester Road corridor, particularly near the Interstate 64 interchange. > > > > 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? > Luxury hotel prices in Winchester vary, but you can find a great deal from CA $124 on Expedia. To find the best prices on luxury stays, be flexible with your dates—typically, off-peak and mid-week stays are cheaper. Sort your search results by "Price: low to high" to see our lowest rates. ### What luxury activities and experiences are there in Winchester? > The best luxury activities and experiences in Winchester revolve around its thoroughbred horse farms, bourbon distilleries, and refined culinary scene. > > > > 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? > There are plenty of ways to save on a luxury hotel in Winchester. Unlock our lowest prices by joining [One Key™](https://www.expedia.ca/welcome-one-key), Expedia's travel rewards program. It's free and easy to sign up, and you can access member perks too. Typically, booking in advance will help you save on your luxury hotel booking. If you're feeling spontaneous, be sure to check for last-minute deals. ### Is it cheaper to book a luxury Winchester hotel and flights as a package? > Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates, and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect travel package. ### Can I cancel my luxury hotel reservation on Expedia? > Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline. This is often within 24-48 hours of your scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. 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