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Holidays in Winter

Choose two or more items and save on your trip:

Top hotels in Winter

Bears Den on Private Lake
Bears Den on Private Lake
W5380 Perch Lake Rd, Winter, WI
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4.6/5Exceptional! (13 reviews)
Great

"Clean, comfy beds, and nice deck. Mosquitoes were thick everywhere up here. Great time!"…"

Reviewed on 7 Sep. 2020

Bears Den on Private Lake
"upscale Accommodations" With an "Up North" Location!
"upscale Accommodations" With an "Up North" Location!
1115 County Hwy W, Winter, WI
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5/5Exceptional! (3 reviews)
We slept wonderfully in the perfectly cozy loft among nature.

"This place was so beautiful and has all the modern conviences of home. Yet is among some of the most beautiful Northern Wi woods. Just what we needed after tapping maple syrup trees all day."…"

Reviewed on 21 Mar. 2021

"upscale Accommodations" With an "Up North" Location!
Summer in Winter (Unit 6)
Summer in Winter (Unit 6)
5346 Island Lake Road, Winter, WI
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4.8/5Exceptional! (62 reviews)
Family vacation

"Great rental with a gorgeous view. Close Atv trails, fun water activities, and fishing. Cabin had lots of movies to watch. Good place to reconnect with the family."…"

Reviewed on 20 Oct. 2020

Summer in Winter (Unit 6)
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 holiday package cost?
Customize your Winter holiday package from just . Choose from any combination of rental cars, flights and hotels to create the getaway you’ve been dreaming about. Remember to add on some tours and experiences!
If I'm not able to travel, can I cancel my Winter holiday package?
Yes, you can cancel your Winter booking if your travel plans have changed. Whether you’ll incur a fee or not depends on your airline, hotel or car rental company. You may be able to change or cancel your booking free of charge if you booked in the last 24 hours. Head to our Customer Service Portal for more information.
How do I get a cheap travel package to Winter?
One of the easiest ways to save money (and time) is to bundle your bookings with Expedia. Flights, hotels, tours and rental cars — we’ve got it all. Pick the combination that best suits you and save up to $200. And of course, we do get that a package deal is never one-size-fits-all. That’s why we offer more than 400 air carriers and 1 000 000 properties throughout the world, so you can craft your very own custom-built Winter getaway.
When is the best time of year to visit Winter?
There are advantages to holidaying in Winter in . You can usually pick up the best deals in this month. , on the other hand, is the most expensive time to visit. If you love the buzz of peak season, visit Winter in . The quieter months of will help you avoid the crowds.
How far in advance should I book my Winter holiday?
Browse Expedia to compare flights as soon as you’ve got your travel dates. You can generally purchase a seat up to 12 months before departure. If you don’t see your preferred carrier, or you’re booking late, don’t stress. Low prices to Winter sometimes emerge within weeks of departure.
What does an Expedia Winter travel package include?
Rental cars, flights and hotels, or any combination of the three — it’s your pick! Whether you’re venturing to Winter with the whole family or adventuring solo, there’s a bundle to match your budget and style. Once you’ve made your booking, why not add on one or two tours and experiences?
What should I know before booking a Winter travel package?
Bundling your bookings into a Winter holiday package is the easiest way to organise your trip. Not only that, you’ll save when you combine your flights, hotels and car rentals. Once you’ve booked, why not add on an activity or a tour?
Does Expedia offer Book Now, Pay Later Winter holiday packages?
If you’re longing for some time away but can’t afford to pay upfront, Expedia can lend a hand with an easy payment option. Thanks to our partnership with online lender Affirm, you can Book Now, Pay Later and start planning your journey today.
Can I choose my airline with a Winter Expedia holiday package?
Yes — that’s the beauty of an Expedia package. You get to decide. We have access to more than 550 airline partners around the world, so you have loads of choice when arranging your Winter getaway.