Winner Holidays

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to S$134 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

Top hotels in Winner

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 S$172 per night from 8 Sept to 9 Sept
S$172
8 Sept - 9 Sept
includes taxes & fees
8.8/10 Excellent! (329 reviews)
"My grandchildren enjoyed the pool and the rollaway bed was so helpful"

Reviewed on 21 Jul, 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 S$103 per night from 24 Aug to 25 Aug
S$103
24 Aug - 25 Aug
includes taxes & fees
7.6/10 Good! (302 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 2 Aug, 2025

Super 8 by Wyndham Winner SD
Warrior INN

Warrior INN

845 SD-44, 39, Winner, SD
Fully refundable
The price is S$110 per night from 12 Aug to 13 Aug
S$110
12 Aug - 13 Aug
includes taxes & fees
10/10 Exceptional! (1 review)
Easy & great check in
"Check in was easy. Tabitha was very helpful & kind."

Reviewed on 5 Aug, 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.

Frequently asked questions

How much does a Winner holiday package cost?
You'll find cheap prices 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 holiday to Winner costs.
What are the cheapest months to go to Winner?
You're likely to find reduced prices and better availability in January, February and March. Take a look at our cheap Winner holiday packages and you could land some excellent off-season deals.
How many days is enough for Winner?
Usually, a handful of days is enough to go to the main sights during your Winner holiday. However, if you prefer to have more time to rest or take day trips, 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 holiday package as early as possible.
Is it cheaper to book a Winner holiday as a package?
An Expedia holiday 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 holiday 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.
How to plan a trip to Winner?

  1. Choose when to get away: Check your calendar and get your bags packed. Your preferred season and the type of activities on offer will also help you decide when to holiday in Winner.
  2. Plan your budget wisely: As well as the cost of your stay, you should consider other expenses. These include flights, transportation and food. Also, put aside some extra funds for unexpected expenses that may crop up during your trip to Winner.
  3. Decide how many days away: Start by listing all the sights and activities you'd like to experience in Winner. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to choose a Winner holiday package that brings all your bookings together.

* 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.