Winner Vacations

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Stay near popular Winner attractions

Winner City Pool

6.0/5 (2 reviews)
This community pool offers a refreshing summer retreat with diving boards and supervised swimming areas. Enjoy family-friendly activities or enroll in American Red Cross swimming lessons during the June-August season.
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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
$118 nightly
The price is $128 total per night from Jul 19 to Jul 20
$128 total
Jul 19 - Jul 20
Total with taxes and fees
8.8/10 Excellent! (364 reviews)
"No coffee in room. Ice machine broken on our floor. Otherwise OK Not my favorite place to stay on our trip."

Reviewed on Jun 21, 2026

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
$79 nightly
The price is $86 total per night from Jul 26 to Jul 27
$86 total
Jul 26 - Jul 27
Total with taxes and fees
7.8/10 Good! (333 reviews)
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Reviewed on Jun 14, 2026

Super 8 by Wyndham Winner SD
Cozy Little Getaway, Winner, SD

Cozy Little Getaway, Winner, SD

Winner SD
$160 nightly
The price is $164 total per night from Jun 28 to Jun 29
$164 total
Jun 28 - Jun 29
Total with taxes and fees
10/10 Exceptional! (13 reviews)
"Was everything we needed"

Reviewed on Jun 12, 2026

Cozy Little Getaway, Winner, SD
See all 33 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.