Tripp County Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Save up to CA $1,096 when you book a flight and hotel together*
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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.

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 $163 per night from Aug 3 to Aug 4
CA $163
CA $177 total
Aug 3 - Aug 4
includes taxes & fees
8.8/10 Excellent! (323 reviews)
"My grandchildren enjoyed the pool and the rollaway bed was so helpful"

Reviewed on Jul. 21, 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 CA $107 per night from Aug 26 to Aug 27
CA $107
CA $116 total
Aug 26 - Aug 27
includes taxes & fees
7.6/10 Good! (295 reviews)
"Thank you for a quiet and comfortable place to stay during our travels"

Reviewed on Jul. 21, 2025

Super 8 by Wyndham Winner SD
Knights Inn Winner

Knights Inn Winner

1.5 out of 5
845 E. Highway 44, Winner, SD
5.2/10 (76 reviews)
"I stayed at this hotel because I was in Winner, South Dakota to go pheasant hunting with my dog. The hotel is absolutely accommodating for hunters with dogs. The staff were friendly and helpful. The hotel has a very good continental breakfast. I will stay in Knights Inn the next time I am hunting ..."

Reviewed on Oct. 23, 2024

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Knights Inn Winner
See all 41 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.
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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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.