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

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

Winner

Winner

Top Tripp County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Miller

Super 8 by Wyndham Miller

2 out of 5
Price was CA $1,275, price is now CA $1,235 per person
CA $1,235
per person
Jul 2 - Jul 7
found 21 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Pierre (PIR)
5.8/10 (122 reviews)
Room was pretty run down, the bed wasn’t made very well. The staff just processed the request and gave me the key card and gave very detailed instructions on how to get to the room. When asked about a plug in for the diesel he was BP dry helpful.

Reviewed on Dec 22, 2025

Best Western Lee's Motor Inn

Best Western Lee's Motor Inn

2.5 out of 5
Price was CA $1,439, price is now CA $1,357 per person
CA $1,357
per person
Jul 4 - Jul 9
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Pierre (PIR)
8.2/10 Very Good! (1,004 reviews)
This was a quick stopover on our way back home on a long road trip. The staff is friendly, the room is clean and it was quiet. The hotel needs some updating but for our needs this hotel for an overnight stopover was all we needed

Reviewed on May 29, 2026

Baymont by Wyndham Oacoma

Baymont by Wyndham Oacoma

2.5 out of 5
Price was CA $1,570, price is now CA $1,529 per person
CA $1,529
per person
Jul 4 - Jul 9
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Pierre (PIR)
8.8/10 Excellent! (1,001 reviews)
Quiet and clean. Adequate breakfast. Right next door to Al's Oasis, which has a decent restaurant/bar and other shops. We had a room with both an outside door and inside door, which was convenient. Only criticisms are that the fan on our airconditioner was quite noisy when set to high and our toilet handle needed to be jiggled to stop it from continuously "flushing". No big deals, really and we'd stay there again on our way across the country.

Reviewed on May 28, 2026

Econo Lodge Oacoma - Chamberlain West

Econo Lodge Oacoma - Chamberlain West

2 out of 5
Price was CA $1,375, price is now CA $1,349 per person
CA $1,349
per person
Jul 2 - Jul 7
found 21 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Pierre (PIR)
7.2/10 Good! (1,001 reviews)
location was convenie t...sign said pool and spa but no pool or spa. Breakfast was good. overall good value for money.

Reviewed on May 25, 2026

Super 8 by Wyndham Chamberlain SD

Super 8 by Wyndham Chamberlain SD

2 out of 5
Price was CA $1,306, price is now CA $1,306 per person
CA $1,306
per person
Jul 4 - Jul 9
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Pierre (PIR)
8.2/10 Very Good! (1,003 reviews)
The location of this Super 8 Wyndham is priceless. Right on the Missouri River and next to the South Dakota Veterans Park. The staff are kind and thoughtful. Couldn't of had a better experience.

Reviewed on May 30, 2026

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 $168 per night from Jun 30 to Jul 1
CA $168
CA $183 total
Jun 30 - Jul 1
includes taxes & fees
8.8/10 Excellent! (361 reviews)
"It is my home away from home. The staff are friendly and helpful. The rooms are always clean and the breakfast is top notch"

Reviewed on May 25, 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 $107 per night from Jun 7 to Jun 8
CA $107
CA $116 total
Jun 7 - Jun 8
includes taxes & fees
7.8/10 Good! (332 reviews)
"Clean and friendly"

Reviewed on May 18, 2026

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)
Not worth a second stop.
"The staff was very friendly, but didn’t make up for the hotel. The most images online are fake and not what it really looks like. There was no sign outside annd the place looked closed. Most of the rooms were under renovation. One of our rooms did not have a chain lock or deadbolt and the shower ..."

Reviewed on Jul 1, 2025

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Knights Inn Winner
See all 61 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 CA $1,235, 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.