Upson Vacations from $1,058

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The Latest Upson vacation packages

Price found within the past 48 hours. Click for updated prices.
Magnuson Hotel Ironwood

Magnuson Hotel Ironwood

2 out of 5
Price was $1,145, price is now $1,058 per person
$1,058
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Orlando (ORL) to Ironwood (IWD)
6.2/10 (339 reviews)

Davos Chalet

Davos Chalet

2 out of 5
Price was $1,542, price is now $1,344 per person
$1,344
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Orlando (ORL) to Ironwood (IWD)
8.6/10 Excellent! (123 reviews)

Quality Inn Ironwood

Quality Inn Ironwood

2.5 out of 5
Price was $1,453, price is now $1,343 per person
$1,343
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Orlando (ORL) to Ironwood (IWD)
8.4/10 Very Good! (649 reviews)

Whitecap Mountains Resort

Whitecap Mountains Resort

2 out of 5
Price was $1,344, price is now $1,251 per person
$1,251
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Orlando (ORL) to Ironwood (IWD)
8.4/10 Very Good! (262 reviews)

Econo Lodge Hurley - Ironwood

Econo Lodge Hurley - Ironwood

2.5 out of 5
Price was $1,120, price is now $1,083 per person
$1,083
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Orlando (ORL) to Ironwood (IWD)
6.8/10 (229 reviews)

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Stay near popular Upson attractions

Whitecap Mountains

9.0/10 (26 reviews)
Hit the slopes in Upson with a visit to Whitecap Mountains. You can enjoy the coffeehouses while in the area.
See properties

Upson Hotel Deals

Whitecap Mountains Resort

Whitecap Mountains Resort

2 out of 5
9106 W County Rd E Upson WI
$160 nightly
The price is $168 total per night from Nov 16 to Nov 17
$168 total
Nov 16 - Nov 17
Total with taxes and fees
Whitecap Mountains Resort
Davos Chalet

Davos Chalet

2 out of 5
11889N Meadow Ln Upson WI
Fully refundableReserve now, pay when you stay
$168 nightly
The price is $177 total per night from Dec 16 to Dec 17
$177 total
Dec 16 - Dec 17
Total with taxes and fees
Davos Chalet
ENTIRE LAKEFRONT 10-bedroom Chateau Getaway at Whitecap Mountains Resort

ENTIRE LAKEFRONT 10-bedroom Chateau Getaway at Whitecap Mountains Resort

Upson WI
9.4/10 Exceptional! (3 reviews)
"Property was great ! Family really enjoyed the getaway. Host responded pretty quickly which was very helpful !"

Reviewed on Sep 6, 2026

Get rates
ENTIRE LAKEFRONT 10-bedroom Chateau Getaway at Whitecap Mountains Resort
See all 434 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 $1,058 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.