Winter Vacations

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Find the Best Winter Vacation Packages

Winter Hotel Deals

Great 4 Season Family Getaway! Quiet, yet full of Fun!

Great 4 Season Family Getaway! Quiet, yet full of Fun!

Winter WI
9.6/10 Exceptional! (76 reviews)
There where a few things we would change but overall a great stay and the view is amazing.. the host is amazing at getting back to us quickly!

Reviewed on 22 September 2025

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Great 4 Season Family Getaway! Quiet, yet full of Fun!
Luxury Cabin, 800+ feet frontage, 733 acre Lake, Hot tub, Pontoon, Fireplace .

Luxury Cabin, 800+ feet frontage, 733 acre Lake, Hot tub, Pontoon, Fireplace .

Winter, Wisconsin WI
10/10 Exceptional! (34 reviews)
The cabin exceeded our expectations in every way. From the cozy heated floors and the inviting fireplace to the fully stocked kitchen, every detail was thoughtfully designed for comfort and convenience. The hot tub was spotless and perfectly hot, offering a relaxing retreat. And the endless supply ...

Reviewed on 3 November 2025

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Luxury Cabin, 800+ feet frontage, 733 acre Lake, Hot tub, Pontoon, Fireplace .
Rustic Cabin on Private Lake

Rustic Cabin on Private Lake

Winter WI
9.2/10 Wonderful! (5 reviews)
Very comfortable and clean. Well stocked. Loons and deer frequent sightings. Easy to communicate with host.

Reviewed on 19 July 2025

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Rustic Cabin on Private Lake
See all 673 properties in Winter
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.

Frequently asked questions

How do I find cheap flights to Winter that have flexible change policies?
At Expedia, we've been channeling our inner Olympic gymnast to provide you with the most flexible airfares on the market. Simply click on "No change fee" right underneath the "Flexible change policies" subheading to find your dream flight to Winter.
Which airlines fly to Winter?
Choose from a variety of airlines that jet into or near Winter. These are some of the best of them:

  • Delta Air Lines - 8,038 flights to or near Winter each month, including 7,977 flights to Minneapolis - St. Paul Intl. Airport (MSP) and 60 to Central Wisconsin Airport (CWA) per month.
  • Sun Country Airlines - 892 flights to or near Winter each month, including 884 flights to Minneapolis - St. Paul Intl. Airport (MSP) and 8 to Chippewa Valley Regional Airport (EAU) per month.
  • American Airlines - 715 flights to or near Winter each month, including 624 flights to Minneapolis - St. Paul Intl. Airport (MSP) and 91 to Central Wisconsin Airport (CWA) per month.

How can I find cheap tickets to Winter?
To score an amazing deal to Winter, book in advance. Also consider using Expedia's handy "flexible dates" feature at the top of your search results. This will show you prices for the days around your travel dates. In the last seven days, was the lowest price for a flight to Winter.
How much is a flight to Winter?
The cost of a round-trip ticket to Winter in the last seven days ranged between and . If you were heading one way from (), you could have gotten a fare from only .
What are the most popular airports to fly into in Winter?
Which airport you touch down at in Winter mostly depends on where you start your journey and where you're heading to. Here's a list of the top airports in this region:

  • Minneapolis - St. Paul Intl. Airport (MSP) - 11,111 flights per month.
  • Central Wisconsin Airport (CWA) - 151 flights per month.
  • Chippewa Valley Regional Airport (EAU) - 8 flights per month.

When is the cheapest time to fly to Winter?
Depart for Winter earlier in the week and you'll usually be rewarded with lower fares. Tuesday is known for being the cheapest day to jet off, closely followed by Monday. If you're eager to avoid the priciest flights, stay away from Saturdays.
How much is a plane ticket to Winter?
Plane tickets to Winter varied from to in the last seven days. Typically, the earlier you book the better the deal.
What months are the cheapest to book a flight to Winter?
February is the cheapest month to book your Winter adventure. Fares cost the most throughout the busy month of December, so keep clear of this time if you can.
How long is a flight to Winter?
Your flight to Winter could be short or it could be long depending on where your point of origin is. Before you load your tablet with movies and podcasts, check out the average flight times for these well-known domestic routes:

  • Denver, CO (DEN-Denver Intl.) to Minneapolis - St. Paul Intl. Airport (MSP) - 2 hours and 3 minutes
  • Chicago, IL (ORD-O'Hare Intl.) to Minneapolis - St. Paul Intl. Airport (MSP) - 1 hour and 40 minutes
  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Minneapolis - St. Paul Intl. Airport (MSP) - 2 hours and 39 minutes