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 SARĀ 450 per night from Aug 3 to Aug 4
SARĀ 450
SARĀ 585 total
3 Aug - 4 Aug
includes taxes & fees
8.6/10 Excellent! (203 reviews)
"I was unaware of the $25 "resort fee", which I had to pay upon check in. I always feel like that's a "cheap way to get more money off people". Come on, just include it in the cost of the room- that was annoying!!"

Reviewed on 15 July 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 SARĀ 490 per night from Jul 20 to Jul 21
SARĀ 490
SARĀ 517 total
20 Jul - 21 Jul
includes taxes & fees
8.6/10 Excellent! (103 reviews)
"Horrible!!! The owner should not have had the place available for renting this last weekend. When I called to get my room number, I was told by the owner that it was project weekend and his son and about 15 friends were there helping him. We show up and can barely walk without tripping through all ..."

Reviewed on 14 July 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 8 March 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.
See properties

Frequently asked questions

How much does a Upson vacation package cost?
Offering great value package deals on Expedia, you'll be surprised at how little a vacation to Upson costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Upson?
The off-season is the best time to travel to Upson if you're on a budget. Another tip for getting cheap Upson vacation packages? Try to avoid visiting during public holidays and any major festivals or events.
How to find the best Upson package deals?
Begin your search for a Upson package deal by entering your preferred travel dates and destination under our "Packages" tab. Then add a few filters, like "Guest rating" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Upson package deal right away, just play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Upson escape off to a flying start.
Is it cheaper to book a Upson vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll generally get a better deal than booking each component separately. And you'll still get the flexibility to create a tailored Upson vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Upson?
If you have your Upson travel dates finalized, book as early as you can to grab some unbeatable deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to Upson?

  1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to travel to Upson.
  2. Calculate your budget: Ensure you have enough money to cover everything from food and transportation to flights and experiences. Your hotel will likely be the largest expense during your trip to Upson.
  3. Decide how many days away: Start by listing all the activities and attractions you'd like to get to in Upson. Then, estimate how long you'll need for each, including any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a customized Upson vacation package.