Title: Winchester Vacation Packages 2026 from $350 | 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://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Winchester Vacations from $350 ## 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. ![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 $350 per person May 7 - May 10 found 1 day ago Roundtrip flight included Dallas (DFW) to Cincinnati (CVG) 8.8/10 Excellent! (1,003 reviews) Room was very clean, breakfast was delicious and complimentary coffee and tea always available. The only downside was that the hot tub was not working and we specifically booked this hotel for it. Reviewed on Feb 12, 2026 ![Great Wolf Lodge Cincinnati/Mason](https://images.trvl-media.com/lodging/2000000/1670000/1661000/1660957/53fc83a3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Great Wolf Lodge Cincinnati/Mason $579 per person May 7 - May 10 found 8 hours ago Roundtrip flight included Dallas (DFW) to Cincinnati (CVG) 8.6/10 Excellent! (1,002 reviews) Room was clean. Staff is friendly, offered everything you needed including a pack n play for a crib. The food was on the pricey end, but there were a lot of options for everyone and the breakfast buffet was always full and fresh during the hours it was open. Reviewed on Feb 13, 2026 ![Holiday Inn Express & Suites Cincinnati Riverfront by IHG](https://images.trvl-media.com/lodging/1000000/50000/42500/42480/a153a670_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Holiday Inn Express & Suites Cincinnati Riverfront by IHG $359 per person May 7 - May 10 found 1 day ago Roundtrip flight included Dallas (DFW) to Cincinnati (CVG) 9/10 Wonderful! (1,055 reviews) The staff are just the most wonderful, helpful people. Everything was clean and comfortable. The pool was awesome, our daughter had fun splashing around a bit. Breakfast hit the spot! We can't wait to come back again. Reviewed on Feb 5, 2026 ![Hyatt Place Cincinnati / Sharonville Convention Center](https://images.trvl-media.com/lodging/1000000/20000/16000/15914/96fcf8cb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Place Cincinnati / Sharonville Convention Center $417 per person May 7 - May 10 found 8 hours ago Roundtrip flight included Dallas (DFW) to Cincinnati (CVG) 8.8/10 Excellent! (1,351 reviews) I would stay at this location again. Reviewed on Feb 12, 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 $597 per person Mar 29 - Apr 1 found 1 day ago Roundtrip flight included Boston (BOS) to Cincinnati (CVG) 8.6/10 Excellent! (1,001 reviews) Room was very nice. Bathroom was parfect Reviewed on Feb 10, 2026 Don't see what you're looking for? See all available trips from Columbus to Winchester [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-13/2026-03-20/?FromAirport=Columbus,%20Ohio,%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 10/10 Exceptional! (277 reviews) Cabin was nice and clean and well stocked. Loved that all rooms are on the same level. Reviewed on Dec 9, 2025 [Get rates](https://expedia.com/Hotel-Search?startDate=2%2F27%2F2026&endDate=2%2F28%2F2026&selected=29913121&PinnedHotelID=29913121&HadPinnedHotel=true®ionId=183815) [](https://expedia.com/Hotel-Search?startDate=2%2F27%2F2026&endDate=2%2F28%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 22 - Feb 23 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%2F22%2F2026&endDate=2%2F23%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 1 - Mar 2 Total with taxes and fees 7.2/10 Good! (556 reviews) Room was clean and service was good Reviewed on Jan 22, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F1%2F2026&endDate=3%2F2%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%2F14%2F2026&endDate=2%2F15%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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