Winner Vacations

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Find the Best Winner Vacation Packages

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
The price is AED 349 per night from Feb 12 to Feb 13
AED 349
AED 379 total
12 Feb - 13 Feb
includes taxes & fees
8.8/10 Excellent! (348 reviews)
Excellent staff

Reviewed on 6 February 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
The price is AED 244 per night from Mar 2 to Mar 3
AED 244
AED 265 total
2 Mar - 3 Mar
includes taxes & fees
7.6/10 Good! (323 reviews)
Staff was very nice, hotel was very clean!

Reviewed on 13 December 2025

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

Cozy Little Getaway, Winner, SD

Winner SD
The price is AED 367 per night from Mar 11 to Mar 12
AED 367
AED 564 total
11 Mar - 12 Mar
includes taxes & fees
10/10 Exceptional! (12 reviews)
Check in and spacious clean house.

Reviewed on 14 November 2025

Cozy Little Getaway, Winner, SD
See all 28 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.

Discover the most popular places to visit in Winner

A golfer about to putt with flag in the background

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

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

Frequently asked questions

How do I find cheap flights to Winner that have flexible change policies?
Search for your low-cost flights to Winner, then click on "No change fee" under the "Flexible change policies" filter. It really is that simple. We know that things can change and flexibility is essential, so book with confidence with Expedia.
Which airlines fly to Winner?
Denver Air Connection is a well-known carrier servicing Winner. Search for a ticket to Pierre Regional Airport (PIR) and you'll have 52 Denver Air Connection flights a month to select from.
How can I find cheap tickets to Winner?
Book ahead of time, travel on a cheaper day, use frequent flyer miles — there are lots of ways! One more is to make the most of Expedia's "flexible dates" function. Search for a Winner flight, then check out the cheapest prices for nearby dates. In the last seven days, the best price for a flight to Winner was .
How much is a flight to Winner?
You could have purchased a round-trip ticket to Winner from anywhere between and in the last seven days. For one-way journeys departing from (), the lowest price during this time was just .
What are the most popular airports to fly into in Winner?
Pierre Regional Airport (PIR) is the main gateway for many traveling to Winner. Approximately 52 flights per month touch down here.
When is the cheapest time to fly to Winner?
Try to leave early in the week to land the best deal to Winner. Tuesday is usually the most cost-effective day to depart, with Monday right behind it. Saturday typically has the highest ticket prices. This is because lots of travelers choose to start their trip on a weekend.
How much is a plane ticket to Winner?
Seats to Winner varied from to in the last seven days. Typically, the quicker you book the better the deal.
What months are the cheapest to book a flight to Winner?
An excellent month to purchase cheap airfares to Winner is February. Remember that in the United States, the most expensive time to secure a ticket is the festive month of December.