Winner Vacations

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Stay near popular Winner attractions

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.
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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
$83 nightly
The price is $90 total per night from Dec 2 to Dec 3
$90 total
Dec 2 - Dec 3
Total with taxes and fees
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
$78 nightly
The price is $85 total per night from Dec 1 to Dec 2
$85 total
Dec 1 - Dec 2
Total with taxes and fees
7.8/10 Good! (354 reviews)
"Decent price and a decent hotel"

Reviewed on Oct 16, 2026

Super 8 by Wyndham Winner SD
Warrior INN

Warrior INN

2 out of 5
845 SD-44 Winner SD
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Warrior INN
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

What's the best vacation package for Winner?
Winner is known for its family-friendly attractions, and a Winner vacation package built around a stay at Holiday Inn Express & Suites Winner by IHG makes a strong choice for families. Rated 7.6 out of 10, this hotel offers an indoor pool and free breakfast, with travelers often noting the clean rooms and good breakfast. It's located about 9 miles from central Winner, providing a comfortable base for exploring the outdoor and nature activities.

For those seeking the best vacation packages in Winner that offer good value, consider a package with a stay at Super 8 by Wyndham Winner SD. Also rated 7.6 out of 10, this hotel provides free breakfast and is pet-friendly, making it convenient for many travelers. Guests frequently highlight the clean rooms and friendly staff, making for a pleasant stay about 9 miles from central Winner.
How can I save money on a Winner vacation package?
When you bundle, you can save up to 30%*. To save money on a Winner package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
What are the top things to do in Winner?
A Winner vacation offers a variety of outdoor and family-friendly attractions to explore:

Browse and book things to do in Winner on Expedia.
Do you need to rent a car in Winner, or is public transport enough?
For a Winner vacation package, a rental car is highly recommended for exploring this outdoor and nature destination. Attractions are spread out, with places like Winner City Park (about 7 miles away) and Brakke Dam (about 12 miles away) requiring transportation to reach. Additionally, Pierre Regional Airport (PIR), the closest major airport, is about 73 miles from Winner, making a car essential for airport transfers and flexible travel. Having your own vehicle allows you to fully experience the scenic views and adventure activities at your own pace.
Are Winner vacation package hotels conveniently located?
Winner vacation package hotels are generally located a short drive from the immediate central area, offering convenient access to local attractions. For instance, Super 8 by Wyndham Winner SD, rated 7.6 out of 10, is about 9 miles from central Winner and about a 10-minute walk from Tripp County Veteran's Memorial, with travelers often noting its quiet atmosphere. Similarly, Holiday Inn Express & Suites Winner by IHG, also rated 7.6 out of 10, is about 9 miles from central Winner and about a 15-minute walk from Tripp County Veteran's Memorial, and is praised for its great staff. This placement means you're well-positioned to explore the area's outdoor and family-friendly attractions.
Can I change or cancel my Winner vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Winner vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Winner vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Winner vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Winner?
To find last-minute vacation packages to Winner, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Winner vacation packages?
Free cancellation on a Winner vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Winner vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Winner getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Winner vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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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.