Winner Vacations from $867

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The Latest Winner vacation packages

Price found within the past 48 hours. Click for updated prices.
Baymont by Wyndham Pierre

Baymont by Wyndham Pierre

2.5 out of 5
Price was $1,004, price is now $867 per person
$867
per person
Jun 20 - Jun 27
found 1 day ago
Roundtrip non-stop flight included
Tucson (TUS) to Pierre (PIR)
7.6/10 Good! (1,002 reviews)
Very clean, quite and I felt.safe. Staff was polite and courteous.

Reviewed on May 5, 2026

Clubhouse Hotel & Suites Pierre

Clubhouse Hotel & Suites Pierre

3.5 out of 5
Price was $1,581, price is now $1,251 per person
$1,251
per person
Jun 20 - Jun 27
found 1 day ago
Roundtrip non-stop flight included
Tucson (TUS) to Pierre (PIR)
8.6/10 Excellent! (1,001 reviews)
This is a fabulous hotel.

Reviewed on May 8, 2026

My Place Hotel - Ft. Pierre, SD

My Place Hotel - Ft. Pierre, SD

2.5 out of 5
Price was $1,269, price is now $1,070 per person
$1,070
per person
Jun 20 - Jun 27
found 1 day ago
Roundtrip non-stop flight included
Tucson (TUS) to Pierre (PIR)
8.6/10 Excellent! (295 reviews)
Great area to stay at.

Reviewed on Oct 8, 2025

Governor's Inn a Travelodge by Wyndham

Governor's Inn a Travelodge by Wyndham

2 out of 5
Price was $1,015, price is now $874 per person
$874
per person
Jun 20 - Jun 27
found 1 day ago
Roundtrip non-stop flight included
Tucson (TUS) to Pierre (PIR)
7.6/10 Good! (1,003 reviews)
Room was nice and clean but had other issues with it. Broken floor tiles in bathroom, peeling paint and burnt out light bulbs. Also the pool was ridiculously cold. Nobody was in it so the hot tub was packed.

Reviewed on Apr 26, 2026

Holiday Inn Express & Suites Fort Pierre by IHG

Holiday Inn Express & Suites Fort Pierre by IHG

2.5 out of 5
Price was $1,188, price is now $1,030 per person
$1,030
per person
Jun 20 - Jun 27
found 1 day ago
Roundtrip non-stop flight included
Tucson (TUS) to Pierre (PIR)
8.4/10 Very Good! (399 reviews)
Could use some improvements but was good overall. However, I could tell the shower was not cleaned because there was a used washrag left from the person before me. Also, the bathroom door lock did not work.

Reviewed on Mar 15, 2026

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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

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

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 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 May 17 to May 18
$128 total
May 17 - May 18
Total with taxes and fees
8.8/10 Excellent! (358 reviews)
We got in at 9 o’clock that night and got up at 5:30 the next morning to go turkey hunt so I really didn’t get to experience a lot

Reviewed on Apr 19, 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
$73 nightly
The price is $79 total per night from May 18 to May 19
$79 total
May 18 - May 19
Total with taxes and fees
7.8/10 Good! (330 reviews)
Room was clean and inviting. We didnt stay for breakfast as this was just a quick stay.

Reviewed on Apr 21, 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 May 14 to May 15
$164 total
May 14 - May 15
Total with taxes and fees
10/10 Exceptional! (12 reviews)
Check in and spacious clean house.

Reviewed on Nov 14, 2025

Cozy Little Getaway, Winner, SD
See all 29 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 from $867 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.