Winner Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NT$25,000 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

Find the Best Winner Vacation Packages

Winner Hotel Deals

Holiday Inn Express & Suites Winner by IHG

Holiday Inn Express & Suites Winner by IHG

1360 E Highway 44 Winner SD
Fully refundable
NT$3,762
NT$4,089 total
Aug 30 - Aug 31
includes taxes & fees
Holiday Inn Express & Suites Winner by IHG
Super 8 by Wyndham Winner SD

Super 8 by Wyndham Winner SD

902 E Highway 44 Winner SD
Fully refundableReserve now, pay when you stay
NT$2,656
NT$2,887 total
Sep 7 - Sep 8
includes taxes & fees
Super 8 by Wyndham Winner SD
Warrior INN

Warrior INN

845 SD-44 Winner SD
Get rates
Warrior INN
See all 34 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.

Stay near popular Winner attractions

Winner Bass Pond

After visiting Winner Bass Pond, make a plan to see the other sights and activities in Winner. Make time to visit the churches and monuments while you're in the area.
See properties

Winner City Park

Winner City Park offers a tranquil retreat with scenic trails along Rosebud Creek and sports facilities. Enjoy family picnics under shaded shelters or participate in seasonal community events showcasing local culture.
See properties

McDonald's Park

This historic playground, established through Shorty McDonald's 1948 bequest, offers a peaceful retreat for Winner families. Children enjoy well-maintained equipment while parents appreciate the park's community legacy.
See properties

Winner Regional Healthcare Center

Though Winner Regional Healthcare Center might be what brings you to town, perhaps you'll have a chance to explore more of Winner while you are here.
See properties

Bailey's Park

This modest neighborhood park offers a peaceful retreat from the urban bustle. Locals gather here for picnics, casual sports, and community events throughout the year.
See properties

Tripp County Veteran’s Memorial

8.8/10 (3 reviews)
This solemn memorial honors local veterans with granite slabs inscribed with hundreds of names from Tripp County. Visit during Memorial Day ceremonies to experience the community's deep appreciation for military service.
See properties

Winner City Pool

6.0/10 (2 reviews)
This community pool offers a refreshing summer retreat with diving boards and supervised swimming areas. Enjoy family-friendly activities or enroll in American Red Cross swimming lessons during the June-August season.
See properties

Frequently asked questions

How much does a Winner vacation 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 vacation 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 vacation 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 vacation. 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 vacation package as early as possible.
Is it cheaper to book a Winner vacation as a package?
An Expedia vacation 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 vacation 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 vacation 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 vacation package that brings all your bookings together.

Explore a world of travel with Expedia

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