Wisconsin may have travel restrictions in place due to COVID-19.

Travel to Winter

Choose two or more items and save on your trip:

Winter Vacation: Coronavirus Information

Most Winter hotels offer free cancellation. Consider booking refundable hotels rather than non-refundable ones. Just look for the ‘free cancellation’ message during your hotel search. Prices can vary, but right now we believe that flexibility matters.

For more information about the impact of COVID-19 on your Winter trip, please visit our Coronavirus Information page (opens in new window).

Top Hotels in Winter

North Wisconsin Private Island Vacation Home!!
North Wisconsin Private Island Vacation Home!!
Winter, WI
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4.9/5Exceptional! (22 reviews)
Wonderful, relaxing stay.

"What a great place, we didn't want to leave and are already planning to come back. Agree with a few other reviews - clearing out some of the underbrush would provide better views of the water. And if you enjoy cooking like we do, the kitchen is sorely lacking in bakeware. We made do. Had an absolutely ..."…"

Reviewed on Oct 11, 2020

North Wisconsin Private Island Vacation Home!!
Beautiful 3 Bedroom Lake Home Near Winter, Wisconsin
Beautiful 3 Bedroom Lake Home Near Winter, Wisconsin
Winter, WI
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4.9/5Exceptional! (7 reviews)
Amazing Fall Trip

"My wife and I had to make some last minute changes to our fall trip, this place was available, so we gave it a try. We are so glad that we did. Christine was so great to work with, if we needed something she was quick to respond. The place was very nice and you can tell that they are in the middle ..."…"

Reviewed on Oct 16, 2020

Beautiful 3 Bedroom Lake Home Near Winter, Wisconsin
Bears Den on Private Lake
Bears Den on Private Lake
Winter, WI
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4.6/5Exceptional! (13 reviews)

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

Reviewed on Sep 7, 2020

Bears Den on Private Lake
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.

What are the advantages of a road trip to Winter?

There’s nothing quite like a Winter road trip. And Expedia makes it easy for you to turn all those road trip ideas into reality. You can find cheap deals on hotels in Winter or bundle your hotels with car rentals to save even more. With our Winter packages, you’ll find hitting the highway for that road trip adventure is more affordable than ever.  

How to plan a road trip to Winter?

Planning a road trip can feel daunting, especially when you’ll be making multiple bookings for your itinerary. But you can find car rentals in Winter and low rates on hotels all in one place— Expedia. How you plan your road trip depends on what’s important to you. People love to take road trips to experience the great outdoors, bond with friends or family and see more of the world. When planning, bundle your car rental and hotel into one discounted package to maximize savings on both. Or, leave room for spontaneity, booking what you need when you need it with our last-minute deals.  

What to do on a road trip to Winter?

When taking a road trip adventure, it’s best to plan how you want to spend your time on your road trip itinerary. We don’t want you to miss out on any of the best things to do in Winter. You can book all the road trip activities on your Winter wishlist, and even plan activities along your route as well.  

How to rent a car for a road trip?

For an epic road trip, you'll need the perfect car. Renting a car for a road trip is the best option that doesn’t put miles or strain on your vehicle, and especially when it's also so affordable. Because when you book on Expedia, it doesn't need to be expensive. You can pick up a cheap car rental and head out to one of these incredible vacation rentals in Winter. And when you bundle car rentals with hotel stays, you'll save even more on each part of your journey.

Frequently asked questions

How much does a Winter vacation package cost?
Customize your Winter vacation 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 vacation 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 $583. And of course, we do get that a package deal is never one-size-fits-all. That’s why we offer more than 550 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 vacationing 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 vacation?
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 vacation package is the easiest way to organize 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 vacation 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 vacation 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.