Winner Vacations

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Discover the most popular places to visit in Winner

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

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.

Winner Country Club

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.

Winner City Pool

Winner Hotel Deals

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
$83 nightly
The price is $90 total per night from Dec 28 to Dec 29
$90 total
Dec 28 - Dec 29
Total with taxes and fees
8.8/10 Excellent! (337 reviews)
Most of the food was good. Eggs a little watery. Rooms clean but stairs were a bit dirty and they had just painted and there was tape left on the door frames. Overall a good facility

Reviewed on Sep 20, 2025

Holiday Inn Express & Suites Winner by IHG
Warrior INN

Warrior INN

845 SD-44 Winner SD
Fully refundable
$59 nightly
The price is $65 total per night from Dec 6 to Dec 7
$65 total
Dec 6 - Dec 7
Total with taxes and fees
6/10 (7 reviews)
After staying there the last 3-4 years due to no other options, I would have given you a very poor rating due to cleanliness and major maintenance issues. But, holy cow, what an improvement this year. Much cleaner and no major issues. Thank you for the improvements

Reviewed on Nov 21, 2025

Warrior INN
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
$63 nightly
The price is $68 total per night from Dec 21 to Dec 22
$68 total
Dec 21 - Dec 22
Total with taxes and fees
7.6/10 Good! (318 reviews)
The rooms are good to sleep in. Management leaves coffee to drink 24-7, some snacks also. Good comfortable rooms.

Reviewed on Dec 2, 2025

Super 8 by Wyndham Winner SD
See all 25 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.

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, Winner Country Club and Tripp County Veteran’s Memorial

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Frequently asked questions

How much does a Winner vacation 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 vacation to Winner costs.
What are the cheapest months to go to Winner?
You can typically find lower rates and better availability in February, November and December. Take a look at our cheap Winner vacation packages and you could score some great off-season discounts.
How many days is enough for Winner?
Generally, a handful of days is enough to go to the top attractions during your Winner vacation. However, if you prefer to have more time to unwind or go on day tours, 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 vacation package as early as possible.
Is it cheaper to book a Winner vacation as a package?
An Expedia vacation 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 vacation 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.
Does Expedia offer Book Now, Pay Later Winner vacation packages?
Set off on your dream getaway to Winner with Expedia's Book Now, Pay Later vacations. There's no need to scrimp and save or wait until your next paycheck — we've partnered with online lender Affirm to offer you flexibility and choice. Our vacation packages with payment plans allow you to spread the total cost across 3, 6 or 12 months. With no late payment fees or extra charges, you can easily stay on budget and snap up travel deals before they disappear.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.