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Due to coronavirus (COVID-19) travel advisories, some destinations may be unavailable for certain dates. Find out more.
Due to coronavirus (COVID-19) travel advisories, some destinations may be unavailable for certain dates. Find out more.

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Winter Vacation

Does Expedia have vacation package to Winter?

Yes! Save cash by booking a Winter vacation package. Just pick your favorite options and Expedia will do the rest.

How much can I save with a Winter vacation package?

Book your package deal today on Expedia and gain savings of up to $583*! It's that simple!

Can I choose my airline with a Winter Expedia vacation package?

With us, you'll have more than 550 airline partners and 750,000 worldwide properties to choose from around the globe, which means your dream vacation is right at your fingertips!

Do I lose money if I change my mind after I have booked my Winter vacation package?

You may cancel or change almost any reservation and you won't have to pay a cancellation fee to us.

What are the best places to visit in Winter?

There are stacks of fantastic things you can do when you're in a new destination. So why not get your trip to Winter off to a flying start by checking out some of our top tips? After all – out there starts here!

Want to alleviate the stress of your hectic life? Savor the fresh air as you go for a romp through Ojibwa State Park. Still got some time to spare? The wider area also boasts fun outdoor activities to get stuck into, such as skiing.

What types of accommodations are available in Winter?

There are currently no Winter properties on Expedia. However, Ladysmith, which is located 20 miles away, has a good selection of options available. The best options in Ladysmith are the Ladysmith Motel & Suites and El Rancho Motel.

Is there an airport in Winter?

Nothing's more satisfying than coming in to land at Sawyer County Airport (HYR) after being stuck in a cramped cabin for hours. Once you've secured your luggage from the carousel and stretched your limbs, you'll be just 25 miles (40 km) from the main streets of Winter.



*Savings based on all vacation package bookings with Flight + Hotel on Expedia.ca from January through December 2019, as compared to price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.


Best Lodging Options Near Winter

See all 186 properties in Winter
North Wisconsin Private Island Vacation Home!!
Reviewed on Jun. 29, 2020
See details
 
North Wisconsin Private Island Vacation Home!!

North Wisconsin Private Island Vacation Home!!

6009 Dobbert Rd., Winter, WI
     
    4.7 of 5
    0.0 out of 5.0 Stars

    Best cabin we stayed in - will be back! Well worth it.

    Summer in Winter
    Reviewed on Jul. 4, 2020
    See details
     
    Summer in Winter

    Summer in Winter

    5346 Island Lake Road, Winter, WI
       
      4.8 of 5
      0.0 out of 5.0 Stars

      We had a great time at Paul’s cabin. It was just like the pictures and we had so much fun. We made great use of the paddle boat, rowboat, kayaks, and fishing poles on the lake and the VHS tapes in the house. The beds were super comfy and he had everything you could need for a getaway. It was great ...

      Summer in Winter
      Reviewed on Jul. 3, 2020
      See details
       
      Summer in Winter

      Summer in Winter

      5344 Island Lake Ln, Unit 5, Winter, WI
         
        4.7 of 5
        0.0 out of 5.0 Stars

        Great place for a family vacation. The lake was great for kayaking and the pontoon was a great addition. Would stay there again

        Bears Den on Private Lake
        Reviewed on Feb. 20, 2020
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        Bears Den on Private Lake

        Bears Den on Private Lake

        W5380 Perch Lake Rd, Winter, WI
           
          4.8 of 5
          0.0 out of 5.0 Stars

          We stayed in the Winter for a vintage snowmobile ride. House is spacious and super clean. Driveway and sidewalks were all cleared of snow. Saw deer walking on the frozen lake right in front of the house. Would definitely reccomend this home!!

          Amazing Sunsets, Peaceful, Well Maintained Lake Home on Beautiful, Barker Lake
          Reviewed on Jun. 23, 2020
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          Amazing Sunsets, Peaceful, Well Maintained Lake Home on Beautiful, Barker Lake

          Amazing Sunsets, Peaceful, Well Maintained Lake Home on Beautiful, Barker Lake

          N7599 Barker Lake Rd, Winter, WI
             
            4.8 of 5
            0.0 out of 5.0 Stars

            Property is as described. Plenty of space for gathering and reminiscing. Would certainly recommend this place to others looking for easy access to surrounding lakes.

            New to Rental Market - Great 4 Season Family Getaway! Quiet, yet Full of Fun!
            Reviewed on Jun. 28, 2020
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            New to Rental Market - Great 4 Season Family Getaway! Quiet, yet Full of Fun!

            New to Rental Market - Great 4 Season Family Getaway! Quiet, yet Full of Fun!

            5008 W Bumble Bee Rd, Winter, WI
               
              5.0 of 5
              0.0 out of 5.0 Stars

              We rented this property to celabrate my wifes birthday with some friends and family. Fantastic views on a beautiful lake! Will be bookmarking this property for future renting!

              Private Modern Home in Rustic Surroundings and Much to Do
              Reviewed on Jul. 3, 2020
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              Private Modern Home in Rustic Surroundings and Much to Do

              Private Modern Home in Rustic Surroundings and Much to Do

              6919 Hemlock Haven Rd, Winter, WI
                 
                5.0 of 5
                0.0 out of 5.0 Stars

                This rental was perfect for our family vacation. Modern, comfortable, well stocked and clean. Colleen and Dean went out of their way to make our stay great! Everyone agreed this is a place we will come back to.

                Beautiful 3 Bedroom Lake Home Near Winter, Wisconsin
                Beautiful 3 Bedroom Lake Home Near Winter, Wisconsin

                Beautiful 3 Bedroom Lake Home Near Winter, Wisconsin

                6641 N Benson Rd, Winter, WI
                   
                  0.0 out of 5.0 Stars

                  This family-friendly Winter holiday home is located on the waterfront, 3.3 mi (5.3 km) from Chequamegon National Forest, and within 20 mi (32 km) of Lake Chippewa and Callahan Lake. Round Lake and Teal Lake are also within 25 miles (40 km).