Title: Book Winner Vacation Packages for 2026 | Expedia.com [Winner Travel Guide](https://expedia.com/Winner.dx175746)[Hotels in Winner](https://expedia.com/Winner-Hotels.d175746.Travel-Guide-Hotels)[Vacation Rentals in Winner](https://expedia.com/Winner-Vacation-Rentals.d175746.Travel-Guide-VacationRentals)[Flights to Winner](https://expedia.com/Cheap-Flights-To-Winner.d175746.Travel-Guide-Flights)[Car Rentals in Winner](https://expedia.com/Car-Rentals-In-Winner.d175746.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Winner Vacations from $1,903 ## 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 Winner vacation packages Price found within the past 48 hours. Click for updated prices. ![Quality Inn Pierre - Fort Pierre](https://images.trvl-media.com/lodging/1000000/30000/21600/21547/08613f14_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Quality Inn Pierre - Fort Pierre $1,903 per person Apr 10 - Apr 16 found 13 hours ago Roundtrip flight included Columbus (GTR) to Pierre (PIR) 7.2/10 Good! (723 reviews) Room was fine: clean, good shower. Breakfast did have waffle maker & eggs/sausage - if you got there before it ran out. Paid $30 EXTRA for a dog, and there was NO GRASS in sight (drive to a park a few blocks away). The motel itself was not as described: no laundry, pool closed down. Reviewed on Feb 17, 2026 ![Clubhouse Hotel & Suites Pierre](https://images.trvl-media.com/lodging/5000000/4930000/4921200/4921151/5d92d5f5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Clubhouse Hotel & Suites Pierre $2,293 per person Apr 10 - Apr 16 found 13 hours ago Roundtrip flight included Columbus (GTR) to Pierre (PIR) 8.6/10 Excellent! (1,002 reviews) Everything was great except for the Tvs. I stayed in to different rooms, both were extremely dark screen. Unable to adjust. Also, the amount of channels was relatively small compared to similar hotels. Reviewed on Feb 9, 2026 ![Days Inn by Wyndham Pierre](https://images.trvl-media.com/lodging/1000000/20000/19000/18949/cc6e63e7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Days Inn by Wyndham Pierre $1,907 per person Apr 10 - Apr 16 found 13 hours ago Roundtrip flight included Columbus (GTR) to Pierre (PIR) 6.4/10 (731 reviews) Clean and reasonably priced. Reviewed on Jan 23, 2026 Don't see what you're looking for? See all available trips from Columbus to Winner [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-20/2026-03-27/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=null&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_175746) ### Discover the most popular places to visit in Winner ![A golfer about to putt with flag in the background](https://images.trvl-media.com/place/6208186/c4697555-d42b-4321-a684-9b61dd506104.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Winner Country Club Enjoy a round of golf in Winner at Winner Country Club. Make time to visit the churches and monuments while you're in the area. [](https://expedia.com/Winner-Country-Club-Winner.d6208186.Vacation-Attraction) #### Tripp County Veteran’s Memorial You can find out about the history of Winner with a stop at Tripp County Veteran’s Memorial. Make time to visit the monuments and churches while you're in the area. [](https://expedia.com/Tripp-County-Veterans-Memorial-Winner.d553248621560511195.Vacation-Attraction) #### Winner City Pool You can take time to visit Winner City Pool during your travels to Winner. Make time to visit the churches and monuments while you're in the area. [](https://expedia.com/Winner-City-Pool-Winner.d553248621560511194.Vacation-Attraction) ## Winner Hotel Deals ![Holiday Inn Express & Suites Winner by IHG](https://images.trvl-media.com/lodging/1000000/910000/903300/903274/85a55cce_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Holiday Inn Express & Suites Winner by IHG 1360 E Highway 44 Winner SD Fully refundable $87 nightly $95 total Mar 23 - Mar 24 Total with taxes and fees 8.8/10 Excellent! (352 reviews) Everything was great!!! Reviewed on Feb 15, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F23%2F2026&endDate=3%2F24%2F2026&selected=903274&PinnedHotelID=903274&HadPinnedHotel=true®ionId=175746) ![Super 8 by Wyndham Winner SD](https://images.trvl-media.com/lodging/2000000/1330000/1329500/1329421/f9a92518_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Super 8 by Wyndham Winner SD 902 E Highway 44 Winner SD Fully refundableReserve now, pay when you stay $69 nightly $75 total Feb 26 - Feb 27 Total with taxes and fees [](https://expedia.com/Hotel-Search?startDate=2%2F26%2F2026&endDate=2%2F27%2F2026&selected=1329421&PinnedHotelID=1329421&HadPinnedHotel=true®ionId=175746) ![Cozy Little Getaway, Winner, SD](https://images.trvl-media.com/lodging/91000000/90850000/90842300/90842218/6457bb88_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Cozy Little Getaway, Winner, SD Winner SD $150 nightly $154 total Feb 27 - Feb 28 Total with taxes and fees 10/10 Exceptional! (12 reviews) Check in and spacious clean house. Reviewed on Nov 14, 2025 [](https://expedia.com/Hotel-Search?startDate=2%2F27%2F2026&endDate=2%2F28%2F2026&selected=90842218&PinnedHotelID=90842218&HadPinnedHotel=true®ionId=175746) [See all 28 properties in Winner](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F21%2F2026&endDate=2%2F22%2F2026®ionId=175746) 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 Winner Vacation Packages ## Winner Essential Information | Language | English | | --------------- | ---------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Population | 2,800 | | Max Temp Winter | 30ºF | | Max Temp Summer | 85ºF | | Top Sights | [Winner City Pool](https://www.expedia.com/Winner-City-Pool-Winner.d553248621560511194.Vacation-Attraction), [Winner Country Club](https://www.expedia.com/Winner-Country-Club-Winner.d6208186.Vacation-Attraction) and [Tripp County Veteran’s Memorial](https://www.expedia.com/Tripp-County-Veterans-Memorial-Winner.d553248621560511195.Vacation-Attraction) | ## 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 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[](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 Winner vacation package cost? ### What are the cheapest months to go to Winner? ### How many days is enough for Winner? ### How to find the best Winner package deals? ### Is it cheaper to book a Winner vacation as a package? ### When to book a vacation package to Winner? ### Does Expedia offer Book Now, Pay Later Winner vacation packages? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near Winner Country Club ](https://www.expedia.com/Winner-Country-Club-Hotels.0-l6208186-0.Travel-Guide-Filter-Hotels) - [Hotels near Winner City Pool 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