Title: Winner Vacation Packages & Trips 2026  | Expedia.ca

[Hotels in Winner](https://expedia.ca/Winner-Hotels.d175746.Travel-Guide-Hotels)[Vacation Rentals in Winner](https://expedia.ca/Winner-Vacation-Rentals.d175746.Travel-Guide-VacationRentals)[Flights to Winner](https://expedia.ca/Cheap-Flights-To-Winner.d175746.Travel-Guide-Flights)[Winner Car Rentals](https://expedia.ca/Car-Rentals-In-Winner.d175746.Car-Rental-Guide)

![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Winner Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to CA $1,096 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

## Ready to book your vacation to Winner?

Choose your dates

## Winner Hotel Deals

![Holiday Inn Express & Suites Winner by IHG](https://images.trvl-media.com/lodging/1000000/910000/903300/903274/0fe420bc_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Holiday Inn Express & Suites Winner by IHG

1360 E Highway 44 Winner SD

Fully refundable

CA $143

CA $156 total

Apr 5 - Apr 6

includes taxes & fees

8.8/10 Excellent! (354 reviews)

Nice clean hotel, and the hot breakfast was good. We wnjoyed the pool and hot tub as well.

Reviewed on Mar 13, 2026

[](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=903274&PinnedHotelID=903274&HadPinnedHotel=true&regionId=175746)

![Super 8 by Wyndham Winner SD](https://images.trvl-media.com/lodging/2000000/1330000/1329500/1329421/0e73c022_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Super 8 by Wyndham Winner SD

902 E Highway 44 Winner SD

Fully refundableReserve now, pay when you stay

CA $94

CA $103 total

Apr 18 - Apr 19

includes taxes & fees

7.8/10 Good! (326 reviews)

Staff is great!

Reviewed on Mar 25, 2026

[](https://expedia.ca/Hotel-Search?startDate=18%2F04%2F2026&endDate=19%2F04%2F2026&selected=1329421&PinnedHotelID=1329421&HadPinnedHotel=true&regionId=175746)

![Warrior INN](https://images.trvl-media.com/lodging/119000000/118550000/118548600/118548519/15a92292_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Warrior INN

845 SD-44 Winner SD

Fully refundable

CA $95

CA $104 total

Apr 4 - Apr 5

includes taxes & fees

6/10 (10 reviews)

Room was clean. Very cold. Had the heat turned up as far as it would go. Laminate floors cold too. Tv quit working. Outside security doors unlocked. No coffee machine or iron. Pretty basic.

Reviewed on Jan 25, 2026

[](https://expedia.ca/Hotel-Search?startDate=04%2F04%2F2026&endDate=05%2F04%2F2026&selected=118548519&PinnedHotelID=118548519&HadPinnedHotel=true&regionId=175746)

[See all 28 properties in Winner](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=01%2F04%2F2026&endDate=02%2F04%2F2026&regionId=175746)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

## Explore a world of travel with Expedia

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- [Things to do in South Dakota ](https://www.expedia.ca/Things-To-Do-In-South-Dakota.d243.Travel-Guide-Activities)

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

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