Winter Vacations

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Find the Best Winter Vacation Packages

Winter Hotel Deals

Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin
Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin
Winter
8.8/10 Excellent! (17 reviews)
Great stay at Bucktail Lodge!
"Owner made the check in process a breeze. Quaint and great spot in a nice location, definitely will be staying again. Thank you Bucktail Lodge!"

Reviewed on 30 November 2024

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Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin
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
10/10 Exceptional! (19 reviews)
"Highly recommend for a Wisconsin North Woods getaway. Luxurious accommodations in a serene environment, very close to a village with basic amenities"

Reviewed on 23 February 2025

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Luxury Cabin, 800+ feet frontage, 733 acre Lake, Hot tub, Pontoon, Fireplace .
6 bedroom 3- bath 16 people capacity pontoon included in Winter Wis.
6 bedroom 3- bath 16 people capacity pontoon included in Winter Wis.
Winter
9.8/10 Exceptional! (52 reviews)
PLENTY OF ROOM
"WILL NEED TO GO BACK IN THE SUMMER TO ENJOY THE LAKE"

Reviewed on 30 January 2025

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6 bedroom 3- bath 16 people capacity pontoon included in Winter Wis.
See all 631 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 much does a Winter vacation package cost?
You can pick up a vacation package to this popular destination on Expedia. But how much your vacation to Winter costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Winter?
The off-season is the best time to visit Winter if you’re on a budget. Another tip for scoring cheap Winter vacation packages? Avoid visiting during public holidays and any major festivals or events.
How to find the best Winter package deals?
Bagging a cheap Winter package deal is a breeze with Expedia. Once you’ve entered your preferred dates and destination under our “Packages” tab, set your budget range, add a few filters and see what’s available. You can personalize your search by “Amenities,” “Property type,” “Traveler experience” and more. Sort the results by “Price: low to high” to view the most economical Winter package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Winter vacation as a package?
You can enjoy significant savings on your Winter escape by booking a customized vacation package. Check the “Package” heading, then enter your travel dates and destination to see the best hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Winter?
If you’ve got your Winter travel dates locked in, book early to score some terrific deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Winter?

  1. Pick the ideal time to travel: Your schedule, favorite season and the type of weather you like can all influence your decision on when to travel to Winter.
  2. Plan your budget wisely: In addition to the cost of your hotel, you should factor in other expenses. These include food, flights and transportation. Also, put aside a little extra for unexpected expenses that may arise during your trip to Winter.
  3. Decide how long to go away for: Now that you know more about Winter, you can figure out the right length of your vacation. Put together a draft plan and allocate enough time to get through everything on your must-do list.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. Now all that’s left is to find a Winter vacation package that brings all your bookings together.