Upson Vacations

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Find the Best Upson Vacation Packages

Upson Hotel Deals

Whitecap Mountains Resort

Whitecap Mountains Resort

2 out of 5
9106 W County Rd E Upson WI
The price is ￥19,371 per night from Aug 8 to Aug 9
￥19,371
￥25,193 total
Aug 8 - Aug 9
includes taxes & fees
8.6/10 Excellent! (199 reviews)
"The staff was fabulous. We stayed 1 night in July while traveling northern Wisconsin. It happened to fall on Friday - great fish fry, coleslaw, waitstaff. Our room was comfortable, great shower, a bit dated. No hairdryer, so used the air conditioner 😅 it was nice to have a bar, but there is no breakfast ..."

Reviewed on Jul 12, 2026

Whitecap Mountains Resort
Davos Chalet

Davos Chalet

2 out of 5
11889N Meadow Ln Upson WI
Fully refundableReserve now, pay when you stay
The price is ￥21,084 per night from Jul 27 to Jul 28
￥21,084
￥22,244 total
Jul 27 - Jul 28
includes taxes & fees
8.6/10 Excellent! (102 reviews)
"The chalet itself was fine and the manager did warn us about college students working there for the summer but they were extremely loud and running all over the building and outside until about 2am. We did get some sleep by turning on the AC fan all night."

Reviewed on Jul 10, 2026

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
9.6/10 Exceptional! (10 reviews)
"Ski slopes were right off the deck. A lot of comfy beds for a big group. We enjoyed the fireplace, sauna and large dining room table for a group. The ski hill had a lot of different runs for all levels. We enjoyed our stay!"

Reviewed on Mar 8, 2026

Get rates
Sleeps 12 4BR/3BA Ski-in/Out Condo WiFi/AC/Lake/ATV/Hike/Snowmobile-Dog Friendly
See all 439 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.

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.
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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?
To score cheap Upson vacation packages, plan your trip outside of peak periods such as public holidays. You'll typically find better availability and lower prices for flights and hotels.
How many days is enough for Upson?
The ideal duration for your Upson vacation depends on what you'd like to do and see. Generally, a few days to a week will give you enough time to tick off all the main sights and explore some hidden treasures along the way.
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.
How to plan a trip to Upson?

  1. Choose the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to visit Upson.
  2. Set a budget: Factor in expenses such as flights, food and transportation when working out how much to put aside for your trip to Upson. Then, select a property that matches your budget, whether that's a low-cost stay or a more luxurious getaway.
  3. Decide how many days away: Start by compiling a list of the attractions you want to experience in Upson. Then, estimate how long you'll need for each, along with any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a tailored Upson vacation package.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.