Title: Winchester Vacation Packages 2026 from $403 | Expedia.com [Winchester Travel Guide](https://expedia.com/Winchester.dx7876)[Hotels in Winchester](https://expedia.com/Winchester-Hotels.d7876.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.com/Winchester-Vacation-Rentals.d7876.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.com/Cheap-Flights-To-Winchester.d7876.Travel-Guide-Flights)[Car Rentals in Winchester](https://expedia.com/Car-Rentals-In-Winchester.d7876.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6056879/31f89911-167f-41d8-88d6-62f9fb8763d2.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Winchester Vacations from $403 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## Your Winchester Vacation Take away the hard part of organizing your next epic adventure with a Winchester vacation package. Whether you're visiting for its landmarks, food or other highlights, this city offers endless possibilities for fun. Every trip to Winchester needs a well-thought-out itinerary. Fill yours with attractions like [Bluegrass Heritage Museum](https://www.expedia.com/Bluegrass-Heritage-Museum-Lexington.d553248621561880736.Vacation-Attraction), [Lykins Park](https://www.expedia.com/Lykins-Park-Winchester.d6263146.Vacation-Attraction) and [Southwind Golf Course](https://www.expedia.com/Southwind-Golf-Course-Lexington.d6263194.Vacation-Attraction). Your ultimate Winchester vacation is just a few clicks away. Browse hotels, airfares and more on Expedia for an adventure that's tailored to suit your travel style. ## The Latest Winchester vacation packages Price found within the past 48 hours. Click for updated prices. ![Capital Plaza Hotel](https://images.trvl-media.com/lodging/1000000/20000/17200/17162/bc1394ea_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Capital Plaza Hotel $403 per person May 16 - May 18 found 11 hours ago Roundtrip non-stop flight included Newark Liberty Intl. Airport (EWR) to Lexington (LEX) 8.2/10 Very Good! (1,040 reviews) This was our 4th stay at this hotel over the past 15 or so years. Previously the hotel was always clean, comfortable and nicely furnished. During our recent stay the rooms were very worn and we discovered the hotel was under renovation. As a result, the hotel was very short staffed, so we received no housekeeping services and had to pick up room supplies at the front desk. The staff we encountered were friendly and efficient. Although our stay was subpar compared to previous stays, it served our purpose. This property will be spectacular after the remodel is complete, until then, you may want to consider staying elsewhere. I feel like we should have been notified of the renovation during the reservation process, so we could have considered alternative arrangements. I'll stay here again after renovations are complete. Reviewed on Feb 22, 2026 ![The Campbell House Lexington, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/30000/27100/27029/2fd2c43b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Campbell House Lexington, Curio Collection by Hilton $867 per person Apr 23 - Apr 26 found 1 day ago Roundtrip flight included Chicago (CHI) to Lexington (LEX) 8.2/10 Very Good! (1,000 reviews) Comfortable clean room, excellent dinner restaurant (Tavern), good complimentary breakfast. Reviewed on Feb 17, 2026 ![Elwood Hotel & Suites](https://images.trvl-media.com/lodging/3000000/2220000/2219800/2219782/f131bcc5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Elwood Hotel & Suites $747 per person Apr 23 - Apr 26 found 1 day ago Roundtrip flight included Chicago (CHI) to Lexington (LEX) 9.4/10 Exceptional! (1,003 reviews) Entire staff is genuine, friendly, attentive, and welcoming. Rooms are clean and very comfortable. On site restaurant has a nice menus and quality of the food preparation is excellent. Reviewed on Feb 24, 2026 ![Courtyard Lexington Keeneland/Airport](https://images.trvl-media.com/lodging/6000000/5060000/5052600/5052551/786af441_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Courtyard Lexington Keeneland/Airport Beaumont Residential $467 per person May 16 - May 18 found 11 hours ago Roundtrip non-stop flight included Newark Liberty Intl. Airport (EWR) to Lexington (LEX) 8.8/10 Excellent! (796 reviews) The staff is very friendly. Rooms are very clean. Located in safe, convenient area. Reviewed on Nov 11, 2025 Don't see what you're looking for? See all available trips from San Antonio to Winchester [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-25/2026-04-01/?FromAirport=San%20Antonio,%20Texas,%20United%20States%20of%20America&Destination=LEX&NumRoom=1&NumAdult=2&NumChild=0&paandie=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.com/deals?rfrr=PKG_SPRING_PROMO_7876) ### Discover the most popular places to visit in Winchester ![Kentucky Horse Park showing land animals](https://images.trvl-media.com/place/6062603/def85b29-11a4-4658-9dd9-2740c5e40aee.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Kentucky Horse Park Experience the exciting worlds of horses and horseracing at this equine theme park with multiple museums in the middle of Kentucky’s horse country. [](https://expedia.com/Kentucky-Horse-Park-Lexington.d6062603.Vacation-Attraction) ![Panorama of an autumn, colorful lawn surrounded by buildings in downtown Lexington, Kentucky](https://images.trvl-media.com/place/6062605/185f7d52-ee3c-4550-bf71-3939a597b217.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### University of Kentucky Explore the campus of University of Kentucky, during your travels in Lexington. Attend a sporting event or simply enjoy the lively bars while you're in the area. [](https://expedia.com/University-Of-Kentucky-Lexington.d6062605.Vacation-Attraction) ![Horse barn in Kentucky](https://images.trvl-media.com/place/6062637/70731c8c-e6e3-4dbe-a5e4-fefcf830477a.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Keeneland Racing Course Enjoy a trip to Keeneland Racing Course and popular activities like horseback riding in Lexington. You can attend a sporting event while in the area. [](https://expedia.com/Keeneland-Racing-Course-Lexington.d6062637.Vacation-Attraction) ### What to do in Winchester ![Bites of the Bluegrass Cocktails & Bites Tour](https://mediaim.expedia.com/localexpert/45058435/250ec6bb-6659-404f-b359-bf9b90bbd676.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Bites of the Bluegrass Cocktails & Bites Tour $105 per adult [](https://expedia.com/things-to-do/bites-of-the-bluegrass-cocktails-bites-tour.a45058435.activity-details) ![Buffalo Trace, Bulleit Distilling and Rabbit Hole Bourbon Tour](https://mediaim.expedia.com/localexpert/50862340/e38df2f9-ca73-4633-a4cc-1621f7f2bc2c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Buffalo Trace, Bulleit, Pappy & Co. and Rabbit Hole Bourbon Tour $325 per adult [](https://expedia.com/things-to-do/buffalo-trace.a50862340.activity-details) ![Distillery District Food & History Tour in Lexington](https://mediaim.expedia.com/localexpert/46476674/653381b4-c4bb-447c-9f8e-83945b73b731.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Distillery District Food & History Tour in Lexington $99 per adult [](https://expedia.com/things-to-do/distillery-district-food-history-tour-in-lexington.a46476674.activity-details) [See all activities in Winchester](https://expedia.com/things-to-do/search?rid=7876) ## Winchester Hotel Deals ![The Manchester ](https://images.trvl-media.com/lodging/93000000/92440000/92430600/92430541/f02815a4_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Manchester 941 Manchester St Lexington KY Fully refundableReserve now, pay when you stay $201 nightly $234 total Mar 22 - Mar 23 Total with taxes and fees 9.6/10 Exceptional! (1,172 reviews) Great experience! Reviewed on Feb 24, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F22%2F2026&endDate=3%2F23%2F2026&selected=92430541&PinnedHotelID=92430541&HadPinnedHotel=true®ionId=7876) ![DoubleTree Suites by Hilton Hotel Lexington](https://images.trvl-media.com/lodging/1000000/10000/9900/9900/f18d8c34_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### DoubleTree Suites by Hilton Hotel Lexington 2601 Richmond Rd Lexington KY Fully refundableReserve now, pay when you stay $118 nightly $137 total Mar 15 - Mar 16 Total with taxes and fees 8.8/10 Excellent! (1,013 reviews) Everything was nice. Reviewed on Feb 23, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F15%2F2026&endDate=3%2F16%2F2026&selected=9900&PinnedHotelID=9900&HadPinnedHotel=true®ionId=7876) ![Hilton Lexington/Downtown](https://images.trvl-media.com/lodging/1000000/10000/2200/2101/b9ab6063_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Lexington/Downtown 369 West Vine Street Lexington KY Fully refundableReserve now, pay when you stay $150 nightly $174 total Mar 8 - Mar 9 Total with taxes and fees 8.4/10 Very Good! (1,000 reviews) Yes everything was good! Reviewed on Feb 20, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F8%2F2026&endDate=3%2F9%2F2026&selected=2101&PinnedHotelID=2101&HadPinnedHotel=true®ionId=7876) [See all 1,169 properties in Winchester](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F26%2F2026&endDate=2%2F27%2F2026®ionId=7876) 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. ## Find the Best Winchester Vacation Packages ## Winchester Essential Information | Language | English | | --------------- | ---------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Closest Airport | Blue Grass Airport (LEX) | | Population | 18,400 | | Max Temp Winter | 40ºF | | Max Temp Summer | 85ºF | | Top Sights | [Bluegrass Heritage Museum](https://www.expedia.com/Bluegrass-Heritage-Museum-Lexington.d553248621561880736.Vacation-Attraction), [Southwind Golf Course](https://www.expedia.com/Southwind-Golf-Course-Lexington.d6263194.Vacation-Attraction) and [Lykins Park](https://www.expedia.com/Lykins-Park-Winchester.d6263146.Vacation-Attraction) | ## 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![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations 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