Winner Vacation Packages 2026 from $569

Winner flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Dew Drop Inn Motel by OYO Miller SD

$569

per person

Mar 25 - Mar 29

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Pierre (PIR)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.

Top Winner hotels deals

Holiday Inn Express & Suites Winner by IHG

1360 E Highway 44 Winner SD

Free Cancellation

$95 nightly

$103 total

Jan 4 - Jan 5

Total with taxes and fees

This hotel features an indoor pool and a gym. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Pool

Breakfast included

Super 8 by Wyndham Winner SD

902 E Highway 44 Winner SD

Free Cancellation

Reserve now, pay when you stay

$71 nightly

$78 total

Jan 10 - Jan 11

Total with taxes and fees

This motel features 3 restaurants and a bar/lounge. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Free parking, a business center, and a coffee shop are also offered.

Breakfast included

Pet friendly

Warrior INN

845 SD-44 Winner SD

Free Cancellation

$67 nightly

$73 total

Jan 3 - Jan 4

Total with taxes and fees

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.

Pet friendly

Parking included

Knights Inn Winner

845 E. Highway 44 Winner SD

Get rates

Free self parking is available and the motel's front desk is staffed around-the-clock. WiFi in public areas is free. A safe deposit box is also provided.

Pet friendly

Parking included

Cozy Little Getaway, Winner, SD

Winner SD

$150 nightly

$154 total

Jan 4 - Jan 5

Total with taxes and fees

This vacation home features laundry facilities.

Kitchen

Washer

Boar's Tusk Lodge

Winner SD

Get rates

This lodge featured laundry facilities and barbecue grills.

Pet friendly

Free WiFi

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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.

Popular places to visit

Winner Country Club

Enjoy a round of golf in Winner at Winner Country Club. Make time to visit the churches and monuments while you're in the area.

Winner City Pool

You can take time to visit Winner City Pool during your travels to Winner. Make time to visit the churches and monuments while you're in the area.

Winner City Park

After visiting Winner City Park, 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.

Frequently asked questions

How much are vacation packages to Winner?

With vacation packages being sold for only $569, you won't need to drain your bank balance to visit Winner. Travelocity is here to help. Bundle your hotels, flights and experiences into a package and land excellent discounts. The more you book, the more you save.

How long should my Winner vacation be?

About 2 nights is what many tourists book for their Winner trip. That's an useful guide, but there's plenty more to explore if you give yourself a couple of extra days.

Where can I get the best vacation package deals for Winner?

Travelocity will be able to help you find a great Winner package deal. With as many as 400 air carriers and 1,000,000 properties around the world, you're bound to be able to craft the perfect itinerary.

Why should I purchase my Winner vacation bundle via Travelocity?

Because we believe in creating special vacation experiences. From hotels and flights to car rentals and activities, everything is at your fingertips. Our customer care is on hand 24/7 to ensure you're being well taken care of. We also have an amazing Price Match Guarantee, so you can lock in your vacation knowing you've landed the best deal possible. If you find a lower price, we'll match it!

Can I save money on my Winner car rental if I book it with hotels and flights?

Combining your bookings into a Winner vacation package will certainly save you money. Book a car and flight; a car, flight and hotel; or a hotel and car. There's no better way to discover the greater Winner region than with your own set of wheels. You can also add experiences and activities to your Travelocity package.

What is there to do in Winner?

While hopping off the tourist trail is no doubt rewarding, you shouldn't miss the big attractions that make a destination famous. Winner City Pool and Winner Country Club are a couple of them in Winner.

Where should I stay when visiting Winner?

If you're searching for a place to spend your nights, have a look at the Holiday Inn Express & Suites Winner, an IHG Hotel. It's the top pick for many visitors.