Title: Winchester Vacation Packages 2026 from $284 | Expedia.com [Winchester Travel Guide](https://expedia.com/Winchester.dx183815)[Hotels in Winchester](https://expedia.com/Winchester-Hotels.d183815.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.com/Winchester-Vacation-Rentals.d183815.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.com/Cheap-Flights-To-Winchester.d183815.Travel-Guide-Flights)[Car Rentals in Winchester](https://expedia.com/Car-Rentals-In-Winchester.d183815.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 $284 ## 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 ## The Latest Winchester vacation packages Price found within the past 48 hours. Click for updated prices. ![Comfort Inn Airport Turfway Road](https://images.trvl-media.com/lodging/1000000/540000/533800/533767/7002ed76_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Comfort Inn Airport Turfway Road $284 per person Apr 17 - Apr 20 found 1 day ago Roundtrip flight included Dallas (DFW) to Cincinnati (CVG) 8.4/10 Very Good! (1,004 reviews) Great room at a great price in a great area. One of the best breakfasts for that price on a room I’ve ever had. We will definitely stay here again if we are in the area. Reviewed on Jan 2, 2026 ![Belterra Casino Resort](https://images.trvl-media.com/lodging/2000000/1160000/1152900/1152807/04047b8f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Belterra Casino Resort Save 100% on your flight $350 per person Apr 17 - Apr 20 found 1 day ago Roundtrip flight included Dallas (DFW) to Cincinnati (CVG) 8.6/10 Excellent! (1,001 reviews) The resort was gorgeous, and the rooms were amazing also. There wasn't as many slots as I would expect but loved the table games! Reviewed on Feb 22, 2026 ![Holiday Inn Express Hotel & Suites Richwood-Cincinnati South by IHG](https://images.trvl-media.com/lodging/4000000/3050000/3040400/3040377/771dbbc8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Holiday Inn Express Hotel & Suites Richwood-Cincinnati South by IHG $304 per person Apr 17 - Apr 20 found 1 day ago Roundtrip flight included Dallas (DFW) to Cincinnati (CVG) 8.8/10 Excellent! (1,003 reviews) The rooms and hotel was very NICE. The staff was super nice and friendly... Reviewed on Feb 23, 2026 ![Hilton Cincinnati Netherland Plaza](https://images.trvl-media.com/lodging/1000000/10000/5900/5818/3a03c8ac_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Cincinnati Netherland Plaza Downtown Cincinnati $657 per person Mar 26 - Mar 29 found 24 hours ago Roundtrip flight included Boston (BOS) to Cincinnati (CVG) 8/10 Very Good! (1,268 reviews) Staff was courteous. Room was clean. Great stay! Reviewed on Feb 22, 2026 ![Comfort Suites Dry Ridge](https://images.trvl-media.com/lodging/45000000/44290000/44286400/44286384/1d314755_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Comfort Suites Dry Ridge $326 per person Apr 17 - Apr 20 found 1 day ago Roundtrip flight included Dallas (DFW) to Cincinnati (CVG) 9.2/10 Wonderful! (1,295 reviews) Breakfast was disappointing. Reviewed on Feb 19, 2026 Don't see what you're looking for? See all available trips from Seattle to Winchester [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-24/2026-03-31/?FromAirport=Seattle,%20Washington,%20United%20States%20of%20America&Destination=CVG&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_183815) ## Winchester Hotel Deals ![Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !](https://images.trvl-media.com/lodging/30000000/29920000/29913200/29913121/43ca7232_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake ! Winchester OH [Get rates](https://expedia.com/Hotel-Search?startDate=3%2F10%2F2026&endDate=3%2F11%2F2026&selected=29913121&PinnedHotelID=29913121&HadPinnedHotel=true®ionId=183815) [](https://expedia.com/Hotel-Search?startDate=3%2F10%2F2026&endDate=3%2F11%2F2026&selected=29913121&PinnedHotelID=29913121&HadPinnedHotel=true®ionId=183815) ![French Quarter Inn](https://images.trvl-media.com/lodging/16000000/15590000/15589500/15589406/w1000h451x0y0-8ba0d251_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### French Quarter Inn 25 East McDonald Parkway Maysville KY Fully refundableReserve now, pay when you stay $110 nightly $122 total Feb 25 - Feb 26 Total with taxes and fees 8.8/10 Excellent! (764 reviews) staff great Reviewed on Feb 8, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F25%2F2026&endDate=2%2F26%2F2026&selected=15589406&PinnedHotelID=15589406&HadPinnedHotel=true®ionId=183815) ![Countryside Inn & Suites](https://images.trvl-media.com/lodging/1000000/330000/327900/327877/2c0e7fee_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Countryside Inn & Suites 100 Leininger Street Mount Orab OH Fully refundableReserve now, pay when you stay $86 nightly $97 total Mar 10 - Mar 11 Total with taxes and fees 7.2/10 Good! (557 reviews) Extra charges that shouldnt of been added plus bugs in room Reviewed on Feb 17, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F10%2F2026&endDate=3%2F11%2F2026&selected=327877&PinnedHotelID=327877&HadPinnedHotel=true®ionId=183815) [See all 147 properties in Winchester](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F25%2F2026&endDate=2%2F26%2F2026®ionId=183815) 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 | | Population | 1,050 | | Max Temp Winter | 40ºF | | Max Temp Summer | 80ºF | ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.com/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.com/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.com/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.com/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ![Gay Friendly Vacations](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ Friendly Vacations [](https://expedia.com/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ_Friendly%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2017/07/05/170615_Adventure_1320_2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adventure Vacations [](https://expedia.com/lp/theme-vacations/adventure-vacations?rfrr=editorial.Adventure_Vacations.click) ![Vacations in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Honeymoon Vacations [](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Mountain Vacations [](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Fishing Vacations [](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](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 [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ## Frequently asked questions ### How much does a Winchester vacation package cost? ### What are the cheapest months to go to Winchester? ### How many days is enough for Winchester? ### How to find the best Winchester package deals? ### Is it cheaper to book a Winchester vacation as a package? ### When to book a vacation package to Winchester? ### Does Expedia offer Book Now, Pay Later Winchester vacation packages? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Seaman Hotels ](https://www.expedia.com/Seaman-Hotels.d181456.Travel-Guide-Hotels) - [Cabin Rentals in Seaman ](https://www.expedia.com/Seaman-Cabins.d181456-aaCabins.Travel-Guide-Accommodation) - [Motels in Seaman ](https://www.expedia.com/Seaman-Motels.d181456-aaMotels.Travel-Guide-Accommodation) - [B&B in Seaman ](https://www.expedia.com/Seaman-Bed-And-Breakfast.d181456-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cottages in Seaman ](https://www.expedia.com/Seaman-Cottages.d181456-aaCottages.Travel-Guide-Accommodation) - [3 Star Hotels in Seaman ](https://www.expedia.com/3Star-Seaman-Hotels.s30-0-d181456.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Seaman ](https://www.expedia.com/5Star-Seaman-Hotels.s50-0-d181456.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Seaman 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