Winner Holidays

    Plan, book, travel with confidence
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    Better together
    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

Top hotels in Winner

Holiday Inn Express & Suites Winner, an IHG Hotel
Holiday Inn Express & Suites Winner, an IHG Hotel
2.5 out of 5
1360 E Highway 44, Winner, SD
Fully refundable
The price is S$132 per night from 16 Dec to 17 Dec
S$132
includes taxes & fees
16 Dec - 17 Dec
8.8/10 Excellent! (290 reviews)
"Never have had a bad stay here. Home away from home"

Reviewed on 6 Oct,2024

Holiday Inn Express & Suites Winner, an IHG Hotel
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 S$98 per night from 16 Dec to 17 Dec
S$98
includes taxes & fees
16 Dec - 17 Dec
7.6/10 Good! (255 reviews)
"Clean, Quiet, and convenient"

Reviewed on 11 Oct,2024

Super 8 by Wyndham Winner SD
Knights Inn Winner
Knights Inn Winner
1.5 out of 5
845 E. Highway 44, Winner, SD
The price is S$124 per night from 16 Dec to 17 Dec
S$124
includes taxes & fees
16 Dec - 17 Dec
5.4/10 (70 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 23 Oct,2024

Knights Inn Winner
See all 18 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.

Frequently asked questions

How much does a Winner holiday package cost?
Less than you might think — from as low as , actually! By bundling hotels, flights and car rentals into a custom-made package, your Winner escape is just a few clicks away.
How do I get a cheap travel package to Winner?
Crafting your own Winner holiday package with Expedia is a smart way to save. We have over 550 partner airlines and 1,000,000 properties around the globe. With such a huge range to select from, you’ll have no trouble pulling together your dream escape.
How far in advance should I book my Winner holiday?
It’s hard to pick the best time for airfares, but we generally say the earlier, the better. Many international journeys on Expedia become available to compare up to 12 months in advance. If you can’t book ahead, fear not. Cheap prices appear from time to time just weeks before departure dates.
What does an Expedia Winner travel package include?
Rental cars, flights and hotels, or any combination of the three — it’s your choice. Whether you’re visiting Winner with the entire family or adventuring with your friends, there’s a bundle to match every style and budget. Once you’ve made your booking, why not add on a couple of tours as well?
What should I know before booking a Winner travel package?
You can save big by combining your airfares, hotels and rental cars. Once you’ve created your package, you can add on things like activities or tours. Your next unforgettable adventure is only a couple of clicks away.
Can I choose my airline with a Winner Expedia holiday package?
Expedia has access to more than 550 airline partners worldwide, so you sure can! Simply select the airline you want and craft the perfect Winner holiday.
If I'm not able to travel, can I cancel my Winner holiday package?
Yes, you can. We totally understand that life happens, so we’re happy to help if you need to make changes to your Winner holiday package. You may be able to amend or cancel your itinerary at no cost if you’ve booked within 24 hours. Your airline, hotel or car rental company may charge you a fee if you booked more than 24 hours ago. Take a look at our Customer Service Portal for more information. Also, be sure to check your itinerary for the finer details on change fees.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.