Upson Vacations

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Discover the most popular places to visit in Upson

Some of the runs can be surprising...such as a sudden set of cliffs. My daughter and I made it down alright but two other skiers became human sleds.

Whitecap Mountains

Hit the slopes in Upson with a visit to Whitecap Mountains. You can enjoy the coffeehouses while in the area.

Whitecap Mountains

Upson Hotel Deals

Whitecap Mountains Resort

Whitecap Mountains Resort

2 out of 5
9106 W County Rd E Upson WI
$189 nightly
The price is $200 total per night from Feb 1 to Feb 2
$200 total
Feb 1 - Feb 2
Total with taxes and fees
8.4/10 Very Good! (178 reviews)
Hot tub wax excellent after a day of skiing. It was nice having the lodging the bar the ski tickets the pool, hot tub right on site. Ski in/ski out.

Reviewed on Dec 20, 2025

Whitecap Mountains Resort
Davos Chalet

Davos Chalet

2 out of 5
11889N Meadow Ln Upson WI
$120 nightly
The price is $126 total per night from Jan 20 to Jan 21
$126 total
Jan 20 - Jan 21
Total with taxes and fees
8.6/10 Excellent! (95 reviews)
It was such a beauitful place to stay especially with the fall colors. There were community snacks including s’mores which was such a great surprise!

Reviewed on Oct 22, 2025

Davos Chalet
Sleeps 12 4BR/3BA Ski-in/Out Condo WiFi/AC/Lake/ATV/Hike/Snowmobile-Dog Friendly

Sleeps 12 4BR/3BA Ski-in/Out Condo WiFi/AC/Lake/ATV/Hike/Snowmobile-Dog Friendly

Upson WI
9.2/10 Wonderful! (5 reviews)
The host was amazing. The property was perfect for our group. It’s so fun to be all together.Highly recommend this property.

Reviewed on Jan 2, 2026

Get rates
Sleeps 12 4BR/3BA Ski-in/Out Condo WiFi/AC/Lake/ATV/Hike/Snowmobile-Dog Friendly
See all 421 properties in Upson
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 Upson Vacation Packages

Upson Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Gogebic County Airport (IWD)
Top Sights
Potato River Falls and Iron County Historical Society Museum

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Frequently asked questions

How much does a Upson vacation package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a vacation to Upson costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Upson?
April, November and December are the best times to search for cheap Upson vacation packages. Choosing to travel in less busy months means you can generally find lower prices on flights and hotels.
How many days is enough for Upson?
Typically, a handful of days is enough to check out the main sights during your Upson vacation. However, if you prefer to have time to chill out or take day trips, consider extending your itinerary.
How to find the best Upson package deals?
Landing a cheap Upson package deal is easy with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your maximum budget, add a couple of filters and see what's available. You can tailor your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Upson package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Upson vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging flights and hotels individually. Better still, you can customize your Upson escape to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Upson?
If you're planning an impromptu Upson vacation, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can score incredible deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Upson vacation packages?
Your Upson break is meant to be an escape from your daily routine, not a reason for money worries. So to give you a bit more flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees 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.