Winner Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
Winner Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 2,800 |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 29ºC |
Top Sights | Winner City Pool, Winner Country Club and Tripp County Veteran’s Memorial |
Top hotels in Winner
Holiday Inn Express & Suites Winner by IHG
1360 E Highway 44 Winner SD
Fully refundable
£94
28 Aug - 29 Aug
includes taxes & fees
8.8/10 Excellent! (392 reviews)
"Everything was wonderful. Book this property with confidence."
Reviewed on 15 Aug 2026
Super 8 by Wyndham Winner SD
902 E Highway 44 Winner SD
Fully refundableReserve now, pay when you stay
£63
4 Sept - 5 Sept
includes taxes & fees
7.8/10 Good! (345 reviews)
"Enjoy staying here. Nothing fancy, just a good clean room to spend the night. Have been staying here for 12 years on my way out to Sturgis."
Reviewed on 16 Aug 2026
Knights Inn Winner
845 E. Highway 44 Winner SD
5.2/10 (76 reviews)
Not worth a second stop.
"The staff was very friendly, but didn’t make up for the hotel. The most images online are fake and not what it really looks like. There was no sign outside annd the place looked closed. Most of the rooms were under renovation. One of our rooms did not have a chain lock or deadbolt and the shower ..."
Reviewed on 1 Jul 2025
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.
Stay near popular Winner attractions
Winner City Pool
6.0/10 (2 reviews)
This community pool offers a refreshing summer retreat with diving boards and supervised swimming areas. Enjoy family-friendly activities or enrol in American Red Cross swimming lessons during the June-August season.
Winner Bass Pond
After visiting Winner Bass Pond, make a plan to see the other sights and activities in Winner. Make time to visit the churches and monuments while you're in the area.
Tripp County Veteran’s Memorial
8.8/10 (3 reviews)
This solemn memorial honours local veterans with granite slabs inscribed with hundreds of names from Tripp County. Visit during Memorial Day ceremonies to experience the community's deep appreciation for military service.
Winner Regional Healthcare Center
If Winner Regional Healthcare Center is what brings you to town, hopefully you'll have a chance to explore more of Winner.
Winner City Park
Winner City Park offers a tranquil retreat with scenic trails along Rosebud Creek and sports facilities. Enjoy family picnics under shaded shelters or participate in seasonal community events showcasing local culture.
McDonald's Park
This historic playground, established through Shorty McDonald's 1948 bequest, offers a peaceful retreat for Winner families. Children enjoy well-maintained equipment while parents appreciate the park's community legacy.
Bailey's Park
This modest area park offers a peaceful retreat from the urban bustle. Locals gather here for picnics, casual sports, and community events throughout the year.
Frequently asked questions
How much does a Winner travel package cost?
Go from wondering to wandering with our Winner travel packages, which start from only . Handpick the hotels and flights that suit your style. Then, add on a few sightseeing tours for a memorable getaway.
If I'm not able to travel, can I cancel my Winner travel package?
We totally get that life sometimes gets in the way of your plans. If you've locked in a Winner travel package and have to amend or cancel it, we can help. We recommend having a look at our Customer Service Portal first for information. But in general, if you've taken out your package in the last 24 hours, you may be able to change your itinerary at no cost. If it's been more than 24 hours, your airline, hotel or car rental company may charge a fee.
How do I get a cheap travel package to Winner?
You'll save piles of cash if you bundle your hotels, flights and car rentals into a Winner travel package. Sometimes cheap means fewer choices. But that's not the case with Expedia. We offer more than 550 partner airlines and 1,000,000 hotels across the world, which means you'll always have plenty of options to choose from. Want to save even more? Add some fun activities to your package deal and unlock even bigger discounts! After all, travel is about more than just getting to your destination.
Does Expedia offer Book Now, Pay Later Winner holidays?
Your bank balance shouldn't get in the way of taking a holiday, so Expedia has devised a solution to help. Thanks to our partnership with online lender Klarna, it's easier than ever to book an incredible getaway without making a dent in your savings. Klarna offers flexible payment options during the checkout process that take the worry out of budgeting for your trip. Consider one of these flexible payment options:
- Pay monthly holidays: Klarna has manageable monthly payment plans that suit all budgets, so you can escape on that well-deserved holiday sooner.
- Pay in instalments holidays: If you'd like to pay off your escape across multiple transactions, holidays paid in instalments might be right for your Book Now, Pay Later holiday through Klarna.
- Low deposit holidays: When you want to jump on an incredible deal but don't have the full amount yet, Klarna's low deposit holiday plan will help you lock in your escape.
What are the top hotels in Winner?
Get your trip off to a good start by reserving a room at Holiday Inn Express & Suites Winner, an IHG Hotel. It's one of most popular properties in Winner. Another leading option is Super 8 by Wyndham Winner SD.
How far in advance should I book my Winner holiday?
While prices change frequently, we generally recommend booking your seats as early as possible. Many international airfares become available on Expedia up to a year in advance. If circumstances have left you booking late, you may still get lucky. Cheaper tickets to Winner occasionally appear just weeks before departure.
What does an Expedia Winner travel package include?
It comes down to what you're after. If you're travelling alone, you might decide to bundle hotels and flights. Bringing the whole family to Winner? A travel package including rental cars, flights and hotels might be a better fit. Expedia gives you the freedom and flexibility to customize your travel package.
What should I know before booking a Winner travel package?
Bundling your bookings into a Winner travel package is the easiest way to organise your trip. Not only that, you'll save big when you combine your hotels, flights and car rentals. Once you've booked, why not add on a day tour or an activity?
Can I choose my airline with a Winner Expedia travel package?
Yes, definitely. Expedia has over 550 airline partners to pick from across the world. With such a big range of choice, finding the right carrier to whisk you off to Winner won't be difficult.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
