Winner Vacations from $337
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The Latest Winner vacation packages
Price found within the past 48 hours. Click for updated prices.
My Place Hotel - Ft. Pierre, SD
$442
per person
Sep 25 - Sep 27
found 1 day ago
Roundtrip flight included
Denver (DEN) to Pierre (PIR)
8.6/10 Excellent! (307 reviews)
Fridge not working and had a pair of dirty shorts in a kitchen drawer. Makes me wonder if it was as even cleaned or just made the bed. Gross
Reviewed on Jul 30, 2026
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 enroll 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 honors 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
Though Winner Regional Healthcare Center might be what brings you to town, perhaps you'll have a chance to explore more of Winner while you are here.
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 neighborhood park offers a peaceful retreat from the urban bustle. Locals gather here for picnics, casual sports, and community events throughout the year.
Winner Hotel Deals
Holiday Inn Express & Suites Winner by IHG
1360 E Highway 44 Winner SD
Fully refundable
$117 nightly
$127 total
Aug 29 - Aug 30
Total with taxes and fees
8.8/10 Excellent! (390 reviews)
"Pretty nice place. Quiet and clean. Pool was nice and clean and well taken care of. Cleaning staff was very shy and quiet. I thought they did a good job cleaning but could smile and say hello instead of acting like they don’t want you there. Maybe it’s a policy not to make eye contact but i feel ..."
Reviewed on Aug 12, 2026
Super 8 by Wyndham Winner SD
902 E Highway 44 Winner SD
Fully refundableReserve now, pay when you stay
$79 nightly
$86 total
Sep 4 - Sep 5
Total with taxes and fees
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 from $337 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.
