Winner Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Winner

Holiday Inn Express & Suites Winner by IHG
Holiday Inn Express & Suites Winner by IHG
2.5 out of 5
1360 E Highway 44, Winner, SD
Fully refundable
8.8/10 Excellent! (309 reviews)
"It was a great place to stay if you are going to Winner SD or around that area in SD"

Reviewed on 21 Jun 2025

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Holiday Inn Express & Suites Winner by IHG
Super 8 by Wyndham Winner SD
Super 8 by Wyndham Winner SD
2 out of 5
902 E Highway 44, Winner, SD
Fully refundableReserve now, pay when you stay
The price is 1.867.039 ₫ per night from 6 Jul to 7 Jul
1.867.039 ₫
2.029.472 ₫ total
6 Jul - 7 Jul
includes taxes & fees
7.6/10 Good! (289 reviews)
"Room was a bit on the watm side and was hard to maintain comfortable level"

Reviewed on 20 Jun 2025

Super 8 by Wyndham Winner SD
Knights Inn Winner
Knights Inn Winner
1.5 out of 5
845 E. Highway 44, Winner, SD
The price is 2.588.751 ₫ per night from 27 Jul to 28 Jul
2.588.751 ₫
2.813.972 ₫ total
27 Jul - 28 Jul
includes taxes & fees
5.2/10 (74 reviews)
"I stayed at this hotel because I was in Winner, South Dakota to go pheasant hunting with my dog. The hotel is absolutely accommodating for hunters with dogs. The staff were friendly and helpful. The hotel has a very good continental breakfast. I will stay in Knights Inn the next time I am hunting ..."

Reviewed on 23 Oct 2024

Knights Inn Winner
See all 23 properties in Winner
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.

Frequently asked questions

How much does a Winner holiday package cost?
You'll find cheap prices on Expedia for your Winner escape. However, a range of factors like the length of stay, hotel choice and season will determine how much your holiday to Winner costs.
What are the cheapest months to go to Winner?
You're likely to find reduced prices and better availability in January, February and March. Take a look at our cheap Winner holiday packages and you could land some excellent off-season deals.
How many days is enough for Winner?
Usually, a handful of days is enough to go to the main sights during your Winner holiday. However, if you prefer to have more time to rest or take day trips, think about extending your itinerary.
How to find the best Winner package deals?
Use Expedia's handy filters to help you find some unbeatable Winner package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or search for Winner package deals in the low season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your holiday package as early as possible.
Is it cheaper to book a Winner holiday as a package?
An Expedia holiday package could score you significant savings when compared to arranging hotels and flights separately. Better still, you can tailor your Winner trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a holiday package to Winner?
Land incredible discounts by booking your flights early with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for an impromptu Winner escape.
How to plan a trip to Winner?

  1. Choose when to get away: Check your calendar and get your bags packed. Your preferred season and the type of activities on offer will also help you decide when to holiday in Winner.
  2. Plan your budget wisely: As well as the cost of your stay, you should consider other expenses. These include flights, transportation and food. Also, put aside some extra funds for unexpected expenses that may crop up during your trip to Winner.
  3. Decide how many days away: Start by listing all the sights and activities you'd like to experience in Winner. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to choose a Winner holiday package that brings all your bookings together.

Popular places to visit

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.

Tripp County Veteran’s Memorial