Winside Vacations from $1,570

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The Latest Winside vacation packages

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Sioux City/Morningside Area

Super 8 by Wyndham Sioux City/Morningside Area

2 out of 5
Price was $1,570, price is now $1,570 per person
$1,570
per person
Jun 12 - Jun 15
found 18 hours ago
Roundtrip flight included
Chicago (MDW) to Sioux City (SUX)
6.2/10 (841 reviews)
Very dirty clogged drains

Reviewed on Dec 5, 2025

Days Inn by Wyndham Sioux City

Days Inn by Wyndham Sioux City

2 out of 5
Price was $1,609, price is now $1,589 per person
$1,589
per person
Jun 12 - Jun 15
found 18 hours ago
Roundtrip flight included
Chicago (MDW) to Sioux City (SUX)
7.6/10 Good! (762 reviews)
Great place to stay when your waiting out blizzard conditions and closed roads

Reviewed on Mar 15, 2026

Super 8 by Wyndham Sioux City South

Super 8 by Wyndham Sioux City South

2 out of 5
Price was $1,602, price is now $1,582 per person
$1,582
per person
Jun 12 - Jun 15
found 18 hours ago
Roundtrip flight included
Chicago (MDW) to Sioux City (SUX)
8.2/10 Very Good! (875 reviews)
The staff was very friendly and accommodating. Room was clean, and beds were comfortable. Breakfast was okay but the coffee was great. Great value for the price.

Reviewed on Feb 28, 2026

New Victorian Inn & Suites in Sioux City, IA

New Victorian Inn & Suites in Sioux City, IA

2.5 out of 5
Price was $1,591, price is now $1,591 per person
$1,591
per person
Jun 12 - Jun 15
found 18 hours ago
Roundtrip flight included
Chicago (MDW) to Sioux City (SUX)
8.8/10 Excellent! (1,005 reviews)
Great room, helpful staff. Will stay again.

Reviewed on Mar 2, 2026

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Winside Hotel Deals

New Victorian Inn Norfolk

New Victorian Inn Norfolk

2.5 out of 5
1001 Omaha Ave Norfolk NE
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $117 total per night from Mar 29 to Mar 30
$117 total
Mar 29 - Mar 30
Total with taxes and fees
8.6/10 Excellent! (1,000 reviews)
Very nice room

Reviewed on Mar 23, 2026

New Victorian Inn Norfolk
Super 8 by Wyndham Wayne

Super 8 by Wyndham Wayne

2 out of 5
610 Tomar Dr Wayne NE
Fully refundableReserve now, pay when you stay
$54 nightly
The price is $62 total per night from Mar 26 to Mar 27
$62 total
Mar 26 - Mar 27
Total with taxes and fees
6.2/10 (456 reviews)
toilet would not flush shower was mediocre floor board trim was off in hallway but it was clean

Reviewed on Mar 25, 2026

Super 8 by Wyndham Wayne
Norfolk Lodge & Suites, an Ascend Collection Hotel

Norfolk Lodge & Suites, an Ascend Collection Hotel

3 out of 5
4200 Norfolk Avenue Norfolk NE
Fully refundableReserve now, pay when you stay
$149 nightly
The price is $167 total per night from Apr 19 to Apr 20
$167 total
Apr 19 - Apr 20
Total with taxes and fees
9.4/10 Exceptional! (660 reviews)
The beer was great. The food was not. We ate here 3 out of 5 nights, food was subpar for the price.

Reviewed on Mar 16, 2026

Norfolk Lodge & Suites, an Ascend Collection Hotel
See all 30 properties in Winside
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.

Find the Best Winside Vacation Packages

Winside Essential Information

Language
English
Currency
U.S dollars
Population
430
Top Sights
Wayne County Museum, Wayne State College and Wayne County Courthouse

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Frequently asked questions

How much does a Winside vacation package cost?
You'll find cheap prices from $1,570 on Expedia for your Winside getaway. However, a range of factors like the season, length of stay and your choice of hotel will influence how much your vacation to Winside costs.
What are the cheapest months to go to Winside?
If you're hoping to snag a cheap Winside vacation package, consider planning a trip in February, September and December. You'll typically find lower rates on airfares and hotels during these quieter months — ideal for a budget-friendly break.
How many days is enough for Winside?
Generally, a handful of days is enough to visit the main attractions during your Winside vacation. However, if you'd like to have more time to chill out or go on day trips, consider extending your itinerary.
How to find the best Winside package deals?
Bagging a cheap Winside package deal is a cinch with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, add some filters and browse what's available. You can personalize your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Winside package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a Winside vacation as a package?
You can enjoy significant savings on your next Winside getaway by booking a customized vacation package. Check the "Package" heading, then enter your travel dates and destination to view the best hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Winside?
Secure fantastic discounts by booking your flights early with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for a spur-of-the-moment Winside getaway.
Does Expedia offer Book Now, Pay Later Winside vacation packages?
Your Winside break is meant to be an escape from your busy life, not a source of money-related stress. So to allow you a bit more flexibility, we've teamed up with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.

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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.