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Save Time and Money with Winter Vacation Packages

Save Time and Money with Winter Vacation Packages

Book a Winter vacation package on Expedia right now! This is by far one of the best ways of saving time and money for your epic getaway.

Reserve your travel package on Expedia and save up to C$590*.

We've got more than 400 partner airlines and 321,000 worldwide properties to select from around the globe, which means your dream vacation is just a few clicks away!

You never have to worry about postponing your travel itinerary, as we don't charge additional cancellation fees for almost all of our reservations.

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.

Winter Accommodations

Expedia presently has no property listings for Winter. However, you'll discover a few places to stay just 20 miles (32 km) away in Ladysmith. The most popular options in Ladysmith are the Ladysmith Motel & Suites and El Rancho Motel.

Nearest Airports to 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.com from January through December 2017, 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. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.

*Savings based on all vacation package bookings with Flight + Hotel on Expedia.ca from January through December 2017, 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.


Top Hotel Deals

See all 170 properties in Winter
Quite, Secluded Vacation Spot
Quite, Secluded Vacation Spot

Quite, Secluded Vacation Spot

Winter, WI
     
    4.9
    of 5, from 9 reviews
    0.0 out of 5.0

    Situated in Winter, this romantic vacation home is 3.9 mi (6.3 km) from Chequamegon National Forest and within 32 mi (52 km) of Teal Wing Golf Club and Memorial Park. The Tee-Away Golf Course and Supper Club and American Birkebeiner Trail are also within 32 mi (52 km).

    Summer in Winter
    Summer in Winter

    Summer in Winter

    Winter, WI
       
      4.6
      of 5, from 19 reviews
      0.0 out of 5.0

      Situated on a lake, this property is 2.1 mi (3.4 km) from Chequamegon National Forest and within 32 mi (52 km) of Teal Wing Golf Club and Hines Park. Park Falls Country Club and American Birkebeiner Trail are also within 32 mi (52 km).

      Summer in Winter
      Summer in Winter

      Summer in Winter

      Winter, WI
         
        4.5
        of 5, from 20 reviews
        0.0 out of 5.0

        Situated in Winter, this property is 2.1 mi (3.4 km) from Chequamegon National Forest and within 32 mi (52 km) of Teal Wing Golf Club and Hines Park. Park Falls Country Club and American Birkebeiner Trail are also within 32 mi (52 km).

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

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

        Winter, WI
           
          4.7
          of 5, from 12 reviews
          0.0 out of 5.0

          Situated on the beach, this vacation home is 0.1 mi (0.1 km) from Chequamegon National Forest and within 32 mi (52 km) of Teal Wing Golf Club and American Birkebeiner Trail. Lumberjack Bowl and National Fresh Water Fishing Hall of Fame and Museum are also within 32 mi (52 km).

          North Wisconsin Private Island Vacation Home!!
          North Wisconsin Private Island Vacation Home!!

          North Wisconsin Private Island Vacation Home!!

          Winter, WI
             
            4.6
            of 5, from 5 reviews
            0.0 out of 5.0

            Situated on a lake, this vacation home is 6.9 mi (11.1 km) from Chequamegon National Forest and within 32 mi (52 km) of Teal Wing Golf Club and Memorial Park. The Tee-Away Golf Course and Supper Club and American Birkebeiner Trail are also within 32 mi (52 km).

            Bears Den on Private Lake
            Bears Den on Private Lake

            Bears Den on Private Lake

            Winter, WI
               
              0.0 out of 5.0

              Situated on a lake, this vacation home is 0.1 mi (0.1 km) from Chequamegon National Forest and within 32 mi (52 km) of Teal Wing Golf Club and Hines Park. American Birkebeiner Trail and Park Falls Country Club are also within 32 mi (52 km).

              Flat Creek Lodge C$127
              Flat Creek Lodge

              Flat Creek Lodge

              10290 State Rd 27 S, Hayward, WI
                 
                4.0
                of 5, from 348 reviews
                2.0 out of 5.0

                Situated in Hayward, this hotel is close to National Fresh Water Fishing Hall of Fame and Museum, Lumberjack Bowl, and Hayward Information Center. Also nearby are Park Theater and Shues Pond Park.

                AmericInn by Wyndham Hayward C$126
                AmericInn by Wyndham Hayward

                AmericInn by Wyndham Hayward

                15601 Hwy. 63 N., Hayward, WI
                   
                  4.0
                  of 5, from 47 reviews
                  2.5 out of 5.0

                  Located in the heart of Hayward, this hotel is within 1 mi (2 km) of Park Theater, Hayward Information Center, and Shues Pond Park. National Fresh Water Fishing Hall of Fame and Museum and Hayward Golf Club are also within 2 mi (3 km).