Winner Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*
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Top Winner Vacation Deals

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

Super 8 by Wyndham Miller

2 out of 5
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Québec (YQB) to Pierre (PIR)
6/10 (101 reviews)
Clean and fine especially for a short trip. Nothing fancy.

Reviewed on Mar. 26, 2025

Dew Drop Inn Motel by OYO Miller SD

Dew Drop Inn Motel by OYO Miller SD

2.5 out of 5
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Québec (YQB) to Pierre (PIR)
7.8/10 Good! (9 reviews)
Good people here. Owner really cares about his property.

Reviewed on Jul. 9, 2025

Days Inn by Wyndham Pierre

Days Inn by Wyndham Pierre

2 out of 5
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Québec (YQB) to Pierre (PIR)
6.4/10 (650 reviews)
The property is convenient. We spent most of our time with relatives in Pierre.

Reviewed on Jul. 8, 2025

Clubhouse Hotel & Suites Pierre

Clubhouse Hotel & Suites Pierre

3.5 out of 5
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Québec (YQB) to Pierre (PIR)
8.8/10 Excellent! (1,006 reviews)
The place was already over priced for what it is, but then after an unfriendly staff member almost finished checking us in, they sprung an additional 50$ fee for amenities. The breakfast was being made with no pride, most hotels I’ve stayed at for half the price were better. At least it had a 24 gym, even tho it had very limited equipment. The bathtub was slightly larger than a regular one. The outdoor area advertised in the picture was just a door to the parking area. I wouldn’t stay here again

Reviewed on Jul. 18, 2025

Super 8 by Wyndham Winner SD

Super 8 by Wyndham Winner SD

2 out of 5
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Québec (YQB) to Pierre (PIR)
7.8/10 Good! (290 reviews)
We didn’t see much of the property as we got in late & left early.

Reviewed on Jun. 29, 2025

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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
The price is CA $141 per night from Jul 27 to Jul 28
CA $141
CA $154 total
Jul 27 - Jul 28
includes taxes & fees
8.8/10 Excellent! (318 reviews)
"Staff were friendly and accommodating"

Reviewed on Jul. 12, 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 $104 per night from Aug 10 to Aug 11
CA $104
CA $113 total
Aug 10 - Aug 11
includes taxes & fees
7.6/10 Good! (291 reviews)
"We didn’t see much of the property as we got in late & left early."

Reviewed on Jun. 29, 2025

Super 8 by Wyndham Winner SD
Knights Inn Winner

Knights Inn Winner

1.5 out of 5
845 E. Highway 44, Winner, SD
5.2/10 (76 reviews)
"I stayed at this hotel because I was in Winner, South Dakota to go pheasant hunting with my dog. The hotel is absolutely accommodating for hunters with dogs. The staff were friendly and helpful. The hotel has a very good continental breakfast. I will stay in Knights Inn the next time I am hunting ..."

Reviewed on Oct. 23, 2024

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Knights Inn Winner
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.

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Frequently asked questions

How much does a Winner vacation package cost?
You can pick up a vacation package to this popular destination from CA $1,130 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.