Tripp County Vacation Packages

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Your Tripp County Vacation

Make planning your next big adventure easy with a Tripp County vacation package. Whether it's the history, cuisine or something else that lures you here, our packages will help you experience the best of it. During your trip to Tripp County, you'll want to get around to a few of its most popular cities. A must-visit? Winner. Expedia has hotels, flights and all your other travel needs to help you organize your own tailored Tripp County vacation today.

Top vacation destinations in Tripp County

An aerial view of a town with a mix of commercial buildings, roads, and green spaces.
FlightsFlightsHotelsHotels

Winner

Winner

Tripp County Hotel Deals

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 CA $140 per night from Aug 13 to Aug 14
CA $140
CA $153 total
Aug 13 - Aug 14
includes taxes & fees
8.8/10 Excellent! (370 reviews)
"Staff was amazing. Hidden gem. Highly recommend."

Reviewed on Jul 16, 2026

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 CA $113 per night from Aug 16 to Aug 17
CA $113
CA $123 total
Aug 16 - Aug 17
includes taxes & fees
7.8/10 Good! (337 reviews)
"Very accommodating"

Reviewed on Jul 8, 2026

Super 8 by Wyndham Winner SD
Warrior INN

Warrior INN

2 out of 5
845 SD-44 Winner SD
Fully refundable
The price is CA $107 per night from Jul 17 to Jul 18
CA $107
CA $117 total
Jul 17 - Jul 18
includes taxes & fees
5.4/10 (12 reviews)
"This property is closed permanently. DO NOT BOOK HERE."

Reviewed on Jul 15, 2026

Warrior INN
See all 68 properties in Tripp County
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Tripp County vacation package cost?
From as little as , you can build your own Tripp County vacation package. Simply bundle hotels, flights and rental cars and be rewarded with discounts.
How do I get a cheap travel package to Tripp County?
Simply by bundling. Flights, hotels and rental cars — combine whatever you need into a Tripp County vacation package to save loads of cash. Score even better deals when you include extras such as day tours to your booking. But that's not the only impressive part. You have the freedom to put together your vacation your own way. We offer more than 550 air carriers and 1,000,000 hotels all over the world, so that everyone has an opportunity to travel and fulfill those vacation fantasies.
What are the top hotels in Tripp County?
Look up Holiday Inn Express & Suites Winner, an IHG Hotel and Super 8 by Wyndham Winner SD in Winner. Any good Tripp County itinerary has to include a stop in this great city!
How far in advance should I book my Tripp County vacation?
It's tricky picking the best time for airfares, but we usually say the earlier, the better. Plenty of international journeys on Expedia become available up to 12 months in advance. If you're booking late, fear not. Discounted prices appear from time to time within a few weeks of departure dates.
What does an Expedia Tripp County travel package include?
Packages include hotels, flights and rental cars, but you can mix and match them to create your perfect Tripp County trip. You can also add on activities and experiences once you've made your booking. You're in the driver's seat! When you combine your bookings with Expedia, you'll get access to discounts you won't find elsewhere.
What should I know before booking a Tripp County travel package?
A travel package can be easier on the hip pocket than individually booking everything you need for your trip. For example, bundle your hotels, flights and rental cars and save a pretty penny. Whatever sort of vacation you're planning, there's bound to be a package that suits your budget.
Can I choose my airline with a Tripp County Expedia vacation package?
Yes — that's one of the best things about an Expedia vacation package. You're the boss! We have more than 550 airline partners across the globe, so you have options galore when putting together your Tripp County getaway.
If I'm not able to travel, can I cancel my Tripp County vacation package?
It's difficult to predict what tomorrow might bring, so it's good to know that you can cancel or change your Tripp County vacation package. If your booking was made in the last 24 hours, you may be eligible for a refund. If it's an older booking, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal for more information.

Stay near popular Tripp County attractions

Winner Country Club

7.4/10 (3 reviews)
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.