Title: Book the Best BUSINESS Hotels in Winchester in 2025 | 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 Business Hotels in Winchester, KY from CA $104 - ![](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 Business Hotels Tonight [Nov 20 - Nov 21](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2025-11-20&endDate=2025-11-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=business_friendly) Tomorrow [Nov 21 - Nov 22](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2025-11-21&endDate=2025-11-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=business_friendly) This weekend [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2025-11-21&endDate=2025-11-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=business_friendly) Next weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2025-11-28&endDate=2025-11-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=business_friendly) ## Top Winchester Business Hotels ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/16300/16227/b2646625.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/16300/16227/51af70a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/20000/16300/16227/09a180f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Winchester Winchester 9.2/10 Wonderful (447) "Would stay there again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patricia CA $119 CA $131 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Lexington-Hotels-Hampton-Inn-Winchester.h16227.Hotel-Information) ![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/25000000/24370000/24362600/24362582/407ca96d.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 Winchester 9.2/10 Wonderful (514) "Nice room, great staff and just and overall great stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kirk A. CA $117 CA $129 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Lexington-Hotels-Holiday-Inn-Express-Lexington-East-Winchester.h24362582.Hotel-Information) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/15300/15247/8485fa77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/15300/15247/5bc6f945.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/cbda8326.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Winchester Hotel Winchester 8.4/10 Very good (999) "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 $107 CA $118 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Lexington-Hotels-Best-Western-Winchester-Hotel.h15247.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/430000/422700/422677/ffbaf3eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/430000/422700/422677/8040bdb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/430000/422700/422677/2b5cc63d.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 Winchester 7.2/10 Good (768) "The room was all that we expected very good. Staff was very friendly." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) LEROY CA $100 CA $110 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Lexington-Hotels-Baymont-By-Wyndham-Winchester.h422677.Hotel-Information) ![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/330000/327900/327866/2f002c60.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) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/330000/327900/327866/df000477.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/330000/327900/327866/9eec7934.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn Winchester Winchester 7.0/10 Good (350) " Nice, new facilities" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Francis CA $94 CA $104 total includes taxes & fees Dec 11 - Dec 12 [](https://www.expedia.ca/Lexington-Hotels-Comfort-Inn.h327866.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/290000/283200/283165/8b90557f.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) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/290000/283200/283165/a68d39be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/290000/283200/283165/d8551f34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Lexington South / Hamburg Lexington 8.6/10 Excellent (1216) "Had a wonderful stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tara CA $117 CA $136 total includes taxes & fees Nov 27 - Nov 28 [](https://www.expedia.ca/Lexington-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Lexington-South-Hamburg.h283165.Hotel-Information) ![Room, 2 Queen Beds, Accessible, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/9200/9195/ad282c12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually decorated, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/10000/9200/9195/43c334e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/10000/9200/9195/0738d2a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed with Sofa bed (Study)](https://images.trvl-media.com/lodging/1000000/10000/9200/9195/196cfeb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Lexington South-Keeneland/Airport Beaumont Residential 8.2/10 Very good (547) "Friendly staff and quiet hotel." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Monica CA $94 CA $110 total includes taxes & fees Dec 20 - Dec 21 [](https://www.expedia.ca/Lexington-Hotels-Hampton-Inn-Lexington-South-KeenelandAirport.h9195.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/90000000/89550000/89542000/89541948/534e6b71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/90000000/89550000/89542000/89541948/d8a1498f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![Studio, 1 King Bed, Refrigerator & Microwave (Wet bar) | Living area](https://images.trvl-media.com/lodging/90000000/89550000/89542000/89541948/887deb48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Nicholasville Brannon Crossing Nicholasville 9.4/10 Exceptional (226) "Great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MATTHEW CA $122 CA $134 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Lexington-Hotels-Hampton-Inn-Nicholasville-Brannon-Crossing.h89541948.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/24000000/23510000/23507600/23507536/21156f9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom (2 Queen Beds and 1 Double Sofa Bed)](https://images.trvl-media.com/lodging/24000000/23510000/23507600/23507536/1306e7f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/24000000/23510000/23507600/23507536/9a94349d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/24000000/23510000/23507600/23507536/1338cec2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Mt Sterling North by IHG Mount Sterling 8.8/10 Excellent (563) "Great stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rhonda CA $166 CA $183 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Mount-Sterling-Hotels-Holiday-Inn-Express-Suites-Mt-Sterling-North.h23507536.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/810000/800900/800890/721376a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, pillowtop beds, desk](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) ![Lobby](https://images.trvl-media.com/lodging/1000000/810000/800900/800890/04e3e24a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Richmond Richmond 9.0/10 Wonderful (1007) "We have stayed a few times here and have always been pleased with cleanliness, nice staff and cost. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Johnna CA $134 CA $148 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Lexington-Hotels-Quality-Inn.h800890.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=2025-12-04&endDate=2025-12-05®ionId=7876&adults=2&travelerType=business_friendly&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AFFINITY_BF_PROMO_7876) ## Top Winchester Hotel Reviews ![Comfort Inn & Suites Lexington - Hamburg I-75](https://images.trvl-media.com/lodging/1000000/30000/27400/27364/25d8ec98_y.jpg) ### Comfort Inn & Suites Lexington - Hamburg I-75 10/10 Excellent "Room was clean and service was great" [](https://expedia.ca/Lexington-Hotels-Comfort-Inn-Suites.h27364.Hotel-Information) ![Fairfield Inn & Suites by Marriott Lexington North](https://images.trvl-media.com/lodging/3000000/2810000/2803700/2803646/6ec64b2f_y.jpg) ### Fairfield Inn & Suites by Marriott Lexington North 10/10 Excellent "The breakfast was adequate, but the staff and location was awesome!" [](https://expedia.ca/Lexington-Hotels-Fairfield-Inn-Suites-By-Marriott-Lexington-North.h2803646.Hotel-Information) ![Hyatt Regency Lexington](https://images.trvl-media.com/lodging/1000000/10000/3500/3461/c0c49295_y.jpg) ### Hyatt Regency Lexington 10/10 Excellent "Very clean " [](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 10/10 Excellent "G" [](https://expedia.ca/Lexington-Hotels-Elwood-Hotel-Suites.h2219782.Hotel-Information) ![Hyatt Place Lexington](https://images.trvl-media.com/lodging/3000000/2060000/2057700/2057644/91e06cc9_y.jpg) ### Hyatt Place Lexington 10/10 Excellent "Staff friendly, room nice, clean" [](https://expedia.ca/Lexington-Hotels-Hyatt-Place-Lexington.h2057644.Hotel-Information) ![GuestHouse Lexington](https://images.trvl-media.com/lodging/1000000/430000/426400/426325/18dc9903_y.jpg) ### GuestHouse Lexington 10/10 Excellent "Room was clean. Was a little upset that the pool was closed" [](https://expedia.ca/Lexington-Hotels-GuestHouse-Lexington.h426325.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 "Yes the staff was excellent the room was very comfortable " [](https://expedia.ca/Lexington-Hotels-Quality-Inn-Lexington.h22656.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 10/10 Excellent " Clean room, extremely helpful and friendly staff. " [](https://expedia.ca/Lexington-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Lexington-South-Hamburg.h283165.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 "Super nice! Great staff and great breakfast! Super clean! " [](https://expedia.ca/Lexington-Hotels-Best-Western-Winchester-Hotel.h15247.Hotel-Information) ## Frequently asked questions ### How much do business-friendly hotels in Winchester cost? > Expect to pay between CA $104 and CA $183 per night for business-friendly hotels in Winchester. Top deals on stays that cater to work-related travellers are a few clicks away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply. ### What are the best business-friendly hotels in Winchester? > Select from multiple business-friendly hotels in Winchester that have a total average guest review rating of 8.4. [Hampton Inn Winchester](https://www.expedia.ca/Lexington-Hotels-Hampton-Inn-Winchester.h16227.Hotel-Information) is a hit with many corporate travellers. This 2.5-stars property features amenities such as a swimming pool and front desk services. [Holiday Inn Express Lexington East - Winchester, an IHG Hotel](https://www.expedia.ca/Lexington-Hotels-Holiday-Inn-Express-Lexington-East-Winchester.h24362582.Hotel-Information) is another sought-after option. It has a 2.5-stars rating and conveniences including a swimming pool and complimentary breakfast. ### How many business-friendly hotels are there in Winchester? > When work takes you to Winchester, there are 5 business-friendly hotels to pick from. These properties offer a well-suited location with the amenities corporate travellers need. ### What are the best cheap business-friendly hotels in Winchester? > [Hampton Inn Winchester](https://www.expedia.ca/Lexington-Hotels-Hampton-Inn-Winchester.h16227.Hotel-Information) is popular with corporate travellers in search of a money-saving option. It has amenities like a swimming pool and WiFi. Another inexpensive stay for a work trip is [Holiday Inn Express Lexington East - Winchester, an IHG Hotel](https://www.expedia.ca/Lexington-Hotels-Holiday-Inn-Express-Lexington-East-Winchester.h24362582.Hotel-Information). A swimming pool and complimentary breakfast are two of the many conveniences here. Rates for business-friendly hotels in Winchester start from only CA $104 per night, so you'll have dollars left over to spend on client entertainment. Want to add some sightseeing to your Winchester work trip? Find time to visit a few fun and free attractions, such as [Lykins Park](https://www.expedia.ca/Lykins-Park-Winchester.d6263146.Vacation-Attraction) and [Community Park](https://www.expedia.ca/Community-Park-Lexington.d6263168.Vacation-Attraction). This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply. ### Are there any family-friendly hotels in Winchester that are also business friendly? > [Hampton Inn Winchester](https://www.expedia.ca/Lexington-Hotels-Hampton-Inn-Winchester.h16227.Hotel-Information) caters to business and leisure guests alike. Complimentary breakfast and a laundry service are just the start of the amenities offered at this 2.5-stars Winchester stay. Alternatively, get away with the family and work remotely at [Red Roof Inn Winchester](https://www.expedia.ca/Lexington-Hotels-Red-Roof-Inn-Lexington-Winchester.h5872.Hotel-Information). Enjoy the use of conveniences such as WiFi and housekeeping services at this 2-stars option. Once you've gotten work out of the way, there are plenty of family-friendly attractions to discover around Winchester. [Bluegrass Heritage Museum](https://www.expedia.ca/Bluegrass-Heritage-Museum-Lexington.d553248621561880736.Vacation-Attraction) and [Community Park](https://www.expedia.ca/Community-Park-Lexington.d6263168.Vacation-Attraction) guarantee fun for all ages. ### Why book your business-friendly hotel in Winchester with Expedia? > With amenities like conference rooms, room service and on-site cafés, our business-friendly properties come with all you'll need to close your important deal — and then unwind! Enter your travel dates and destination and we'll help you with everything else. ### How can I find cheap business-friendly hotels in Winchester? > Expedia can help you narrow down your search for cheap business-friendly hotels in Winchester. Simply go to our "traveller experience" filter and click on "business friendly." This will show you stays with amenities designed to help you work productively and comfortably, like included breakfast and free WiFi. You can also choose your budget and hotel star rating to keep costs within range. ### What is there to do in Winchester near my business-friendly hotel? > The perfect travel accessory is a well-planned to-do list. [Bluegrass Heritage Museum](https://www.expedia.ca/Bluegrass-Heritage-Museum-Lexington.d553248621561880736.Vacation-Attraction) is a terrific place to begin your sightseeing in Winchester. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [Hotels near Applebee s Park](https://www.expedia.ca/Applebee-S-Park-Hotels.0-l553248621557921127-0.Travel-Guide-Filter-Hotels) - [Motels in Camargo](https://www.expedia.ca/Camargo-Motels.d553248634998850038-aaMotels.Travel-Guide-Accommodation) - [Chevy Chase Hotels](https://www.expedia.ca/Chevy-Chase-Lexington-Hotels.0-n553248635976481361-0.Travel-Guide-Filter-Hotels) - [Hotels near Claiborne Farm](https://www.expedia.ca/Claiborne-Farm-Hotels.0-l553248621559866398-0.Travel-Guide-Filter-Hotels) - [Cabin Rentals in Clay City](https://www.expedia.ca/Clay-City-Cabins.d3000438412-aaCabins.Travel-Guide-Accommodation) - [Guest Houses in Clay City](https://www.expedia.ca/Clay-City-Guest-Houses.d3000438412-aaGuestHouses.Travel-Guide-Accommodation) - 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