Winner Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    Rest easy

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

Ready to book your vacation to Winner?

 

Choose your dates

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 CA $153 per night from Aug 17 to Aug 18
CA $153
CA $167 total
Aug 17 - Aug 18
includes taxes & fees
8.6/10 Excellent! (330 reviews)
"My grandchildren enjoyed the pool and the rollaway bed was so helpful"

Reviewed on Jul. 21, 2025

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 CA $96 per night from Sep 12 to Sep 13
CA $96
CA $105 total
Sep 12 - Sep 13
includes taxes & fees
7.6/10 Good! (303 reviews)
It's okay!
"The room was clean. The bathroom was not, there were pubic hairs left from the former guests in the tub."

Reviewed on Aug. 2, 2025

Super 8 by Wyndham Winner SD
Warrior INN

Warrior INN

845 SD-44, 39, Winner, SD
Fully refundable
The price is CA $109 per night from Sep 14 to Sep 15
CA $109
CA $118 total
Sep 14 - Sep 15
includes taxes & fees
10/10 Exceptional! (1 review)
Easy & great check in
"Check in was easy. Tabitha was very helpful & kind."

Reviewed on Aug. 5, 2025

Warrior INN
See all 24 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Winner vacation package cost?
You can pick up a vacation package to this popular destination on Expedia. But how much your vacation to Winner costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Winner?
January, February and March are the best times to look for cheap Winner vacation packages. Choosing to travel in quieter months means you can typically find reduced prices on accommodations and flights.
How many days is enough for Winner?
The ideal length of your Winner vacation depends on what you'd like to see. Generally, a few days to a week will give you time to visit all the top sights and explore some hidden gems along the way.
How to find the best Winner package deals?
Start your search for a Winner package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply some filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Winner package deal right away, just switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Winner adventure off to a flying start.
Is it cheaper to book a Winner vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll typically snag a better deal than booking each component individually. And you'll still enjoy the freedom to create a customized Winner vacation by choosing your favourite type of stay, airline and car class.
When to book a vacation package to Winner?
If you've got your Winner vacation dates locked in, book as soon as you can to snap up some terrific deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Winner?

  1. Choose the perfect time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to visit Winner.
  2. Plan your budget wisely: In addition to the price of your accommodations, you'll need to factor in other expenses. These include food, transportation and flights. Also, put aside some extra funds for unexpected expenses that may crop up during your trip to Winner.
  3. Determine how many days away: Start by making a list of all the attractions and activities you'd like to experience in Winner. Then, estimate how long you'll need for each, including any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a customized Winner vacation package.

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