Winner Vacations from $486

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Winner vacation packages

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Pierre SD

Super 8 by Wyndham Pierre SD

2 out of 5
Price was $585, price is now $486 per person
$486
per person
Aug 31 - Sep 7
found 22 hours ago
Roundtrip non-stop flight included
Seattle (SEA) to Pierre (PIR)
6.8/10 (1,000 reviews)
The tv didnt work in the room.

Reviewed on Nov 14, 2025

The Outpost Lodge

The Outpost Lodge

3 out of 5
Price was $854, price is now $672 per person
$672
per person
Aug 31 - Sep 7
found 22 hours ago
Roundtrip non-stop flight included
Seattle (SEA) to Pierre (PIR)
8.4/10 Very Good! (73 reviews)
No dishes in the kitchen. No wifi. Beautiful lake view. Friendly staff.

Reviewed on Mar 21, 2026

Baymont by Wyndham Pierre

Baymont by Wyndham Pierre

2.5 out of 5
Price was $666, price is now $558 per person
$558
per person
Aug 31 - Sep 7
found 22 hours ago
Roundtrip non-stop flight included
Seattle (SEA) to Pierre (PIR)
7.6/10 Good! (1,006 reviews)
No shampoo or ice. Holes on top sheet. Staff blamed owner. Also, leg on chair not stable. It was disappointing but that does explain the somewhat reasonable rate. Finally, the breakfast was low end for a “buffet”…….pre formed eggs and small sausage patties. Only dairy in gallon jugs. Again, not the worst but definitely read reviews before relying on the pretty pictures and flowery descriptions.

Reviewed on Jun 14, 2026

Holiday Inn Express & Suites Fort Pierre by IHG

Holiday Inn Express & Suites Fort Pierre by IHG

2.5 out of 5
Price was $837, price is now $720 per person
$720
per person
Aug 31 - Sep 7
found 22 hours ago
Roundtrip non-stop flight included
Seattle (SEA) to Pierre (PIR)
8.4/10 Very Good! (402 reviews)
The roll in shower with the safety handles made the weekend for me. The room was large enough I could invite friends and family over to watch tv and visit with. Thank you. I will remember this room the next time I am in Pierre.

Reviewed on Jun 9, 2026

Quality Inn Pierre - Fort Pierre

Quality Inn Pierre - Fort Pierre

2.5 out of 5
Price was $619, price is now $566 per person
$566
per person
Aug 31 - Sep 7
found 22 hours ago
Roundtrip non-stop flight included
Seattle (SEA) to Pierre (PIR)
7/10 Good! (777 reviews)
Check in was quick and the room was very nice.

Reviewed on Jun 14, 2026

Don't see what you're looking for?
See all available trips from Columbus to Winner
View all trips

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
$114 nightly
The price is $124 total per night from Jul 19 to Jul 20
$124 total
Jul 19 - Jul 20
Total with taxes and fees
8.8/10 Excellent! (363 reviews)
"Everything was good"

Reviewed on Jun 10, 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
$77 nightly
The price is $84 total per night from Jun 28 to Jun 29
$84 total
Jun 28 - Jun 29
Total with taxes and fees
7.8/10 Good! (333 reviews)
"."

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 23 to Jun 24
$164 total
Jun 23 - Jun 24
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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Winner vacation package cost?
You'll find cheap prices from $486 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.