Tripp County Vacation Packages 2026

Search vacation packages deals in Tripp County's top destinations

Aerial View of Sturgis, South Dakota Which hosts an annual Motorcycle Rally

Winner

Vacations

Top Tripp County hotels deals

Holiday Inn Express & Suites Winner by IHG

1360 E Highway 44 Winner SD

Free Cancellation

$95 nightly

$103 total

Jan 27 - Jan 28

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

$60 nightly

$66 total

Feb 8 - Feb 9

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

$70 nightly

$76 total

Jan 25 - Jan 26

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

$145 nightly

$148 total

Jan 29 - Jan 30

Total with taxes and fees

This vacation home features laundry facilities.

Kitchen

Washer

The Ranch You Love

Dallas SD

$269 nightly

$282 total

Jan 31 - Feb 1

Total with taxes and fees

This vacation home featured laundry facilities and barbecue grills.

Kitchen

Washer

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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.

Photos of local treasures

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This was one of the pretty sights. We climbed lots of cliffs. It was very pretty.💍

Frequently asked questions

How much are vacation packages to Tripp County?

Your vacation daydreams can be realized in Tripp County from just . Packages include flights and hotels, so booking your trip will be a breeze. All you'll have to worry about is getting out there and having a great time.

Where can I get the best vacation package deals for Tripp County?

You'll find a terrific selection of Tripp County package deals on Travelocity. With no less than 400 airlines and 1,000,000 properties across the globe, piecing together your ultimate getaway will be a breeze.

Why should I purchase my Tripp County vacation package with Travelocity?

With our Price Match Guarantee, we'll match any better price you're able to find. Add on our 24/7 support and top-shelf service and the vacation of your dreams is closer than ever before.

Will I save money on my Tripp County car rental if I book it with my hotel or flight?

Absolutely. And our Tripp County vacation packages are the perfect way to do it. With only a few clicks you can save cash as well as time by combining your bookings. Collect the keys to your rental car and do your vacation your way. Searching for things to do? Add a few tours to your package and save on those too.

What is there to do in Tripp County?

A diverse and impressive destination, Tripp County boasts some fantastic landmarks. Winner City Pool and Winner Country Club are some of the favorites.