Upson Vacations from $1,080

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The Latest Upson vacation packages

Price found within the past 48 hours. Click for updated prices.
Davos Chalet

Davos Chalet

2 out of 5
Price was $1,292, price is now $1,080 per person
$1,080
per person
Jan 5 - Jan 9
found 1 day ago
Roundtrip flight included
Augusta (AGS) to Ironwood (IWD)
8.8/10 Excellent! (94 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

North Star Retreat-kayak I Swim I Snowmobile

North Star Retreat-kayak I Swim I Snowmobile

2 out of 5
Price was $1,773, price is now $1,590 per person
$1,590
per person
Jan 5 - Jan 9
found 1 day ago
Roundtrip flight included
Augusta (AGS) to Ironwood (IWD)
No reviews
Lakeside Haus in Presque Isle

Lakeside Haus in Presque Isle

2 out of 5
Price was $1,731, price is now $1,564 per person
$1,564
per person
Jan 5 - Jan 9
found 1 day ago
Roundtrip flight included
Augusta (AGS) to Ironwood (IWD)
No reviews
Quality Inn Ironwood

Quality Inn Ironwood

2.5 out of 5
Price was $1,280, price is now $1,173 per person
$1,173
per person
Jan 5 - Jan 9
found 1 day ago
Roundtrip flight included
Augusta (AGS) to Ironwood (IWD)
8.6/10 Excellent! (535 reviews)
I do like an elevator when bring in your suitcase up and Ironwood location does not have that. Also, when traveling with another person, I would like to be able to split the room bill between 2 credit cards.

Reviewed on Sep 14, 2025

Days Inn by Wyndham Hurley

Days Inn by Wyndham Hurley

2 out of 5
Price was $1,296, price is now $1,190 per person
$1,190
per person
Jan 5 - Jan 9
found 1 day ago
Roundtrip flight included
Augusta (AGS) to Ironwood (IWD)
8.4/10 Very Good! (892 reviews)
Was a good place to stay, last time we were in however the hottub was out of order and they did not inform us of this before check-in. That was really the only disappointment. Breakfasts were excellent for a Hotel style free breakfast. Room was clean and our stay was quiet.

Reviewed on Oct 20, 2025

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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

4.5/5(11 reviews)

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
$140 nightly
The price is $149 total per night from Dec 2 to Dec 3
$149 total
Dec 2 - Dec 3
Total with taxes and fees
8.4/10 Very Good! (178 reviews)
Amazingly room and facilities

Reviewed on Nov 26, 2025

Whitecap Mountains Resort
Davos Chalet

Davos Chalet

2 out of 5
11889N Meadow Ln Upson WI
Fully refundableReserve now, pay when you stay
$132 nightly
The price is $140 total per night from Nov 30 to Dec 1
$140 total
Nov 30 - Dec 1
Total with taxes and fees
8.6/10 Excellent! (94 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
Spacious 10-bedroom chalet with WiFi and AC in delightful Upson - Floor 2

Spacious 10-bedroom chalet with WiFi and AC in delightful Upson - Floor 2

2 out of 5
Upson WI
$1,626 nightly
The price is $1,715 total per night from Dec 1 to Dec 2
$1,715 total
Dec 1 - Dec 2
Total with taxes and fees
10/10 Exceptional! (1 review)
Winter Fun
A large group of us rented the Davos Chalet for a long weekend. There was more than enough room for us all. The common area was great for us to eat meals and hang out. The kids loved the game room in the basement.

Reviewed on Mar 24, 2025

Spacious 10-bedroom chalet with WiFi and AC in delightful Upson - Floor 2
See all 407 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 from $1,080 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.