Book Holiday Homes in Winter

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Featured Holiday Homes in Winter

North Fork Flambeau River near Park Falls, 3BR, 1BA country home, on ATV route.

North Fork Flambeau River near Park Falls, 3BR, 1BA country home, on ATV route.

Park Falls
Located in Park Falls, this vacation home is on the waterfront, within a 15-minute drive of Flambeau River and Flambeau Hospital.
North Fork Flambeau River near Park Falls, 3BR, 1BA country home, on ATV route.
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
Located in Winter, this vacation home is on the waterfront, within a 15-minute drive of Chequamegon National Forest and Ojibwa State Park.
6 bedroom 3- bath 16 people capacity pontoon included in Winter Wis.
Secluded 4-season cabin w/private waterfront, epic game room & mins from trails

Secluded 4-season cabin w/private waterfront, epic game room & mins from trails

Hayward
Located in Hayward, this vacation home is on the waterfront, within a 15-minute drive of Tiger Cat Flowage and Chequamegon National Forest.
Secluded 4-season cabin w/private waterfront, epic game room & mins from trails
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Spacious Lake Home near Ladysmith, with a private dock on the Dairyland Flowage!

Spacious Lake Home near Ladysmith, with a private dock on the Dairyland Flowage!

Tony
Located in Tony, this vacation home is on the waterfront, a 1-minute drive from Flambeau River and 6 minutes from Josie Creek County Park.
Spacious Lake Home near Ladysmith, with a private dock on the Dairyland Flowage!
Whispering Pines Hideaway overlooking  peaceful Lake Gurno!

Whispering Pines Hideaway overlooking peaceful Lake Gurno!

Hayward
Located in Hayward, this vacation home is on the waterfront, a 1-minute drive from Lac Courte Oreilles and 5 minutes from Grindstone Lake.
Whispering Pines Hideaway overlooking peaceful Lake Gurno!
Cozy Lake Home in Woods Near Hayward! Close Trails, Fishing, Fun Await!

Cozy Lake Home in Woods Near Hayward! Close Trails, Fishing, Fun Await!

Hayward
A stay at this vacation home places you in the heart of Hayward, a 1-minute drive from Tiger Cat Flowage and 13 minutes from Round Lake.
Cozy Lake Home in Woods Near Hayward! Close Trails, Fishing, Fun Await!
Bungalow Trail

Bungalow Trail

Winter
Located in Winter, this vacation home is on the waterfront, within a 15-minute drive of Ojibwa State Park and Chequamegon National Forest.
Bungalow Trail
Cozy log home on 6 acres - Hayward

Cozy log home on 6 acres - Hayward

Hayward
Located in Hayward, this vacation home is in a rural location, within a 15-minute drive of Round Lake and Sevenwinds Casino.
Cozy log home on 6 acres - Hayward
Lake Hayward.  Private Lakefront Within Walking Distance To Downtown Hayward

Lake Hayward. Private Lakefront Within Walking Distance To Downtown Hayward

Hayward
A stay at this vacation home places you in the heart of Hayward, steps from Hayward Lake and 3 minutes by foot from Lumberjack Bowl.
Lake Hayward. Private Lakefront Within Walking Distance To Downtown Hayward
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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.

Winter Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Winter vacation homes are the perfect way for you to wing it.

Holiday houses in Winter let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Winter in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Winter adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Winter with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Winter vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Winter Holiday Homes essential information

Accommodation
105 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
North Fork Flambeau River near Park Falls, 3BR, 1BA country home, on ATV route., 6 bedroom 3- bath 16 people capacity pontoon included in Winter Wis., Secluded 4-season cabin w/private waterfront, epic game room & mins from trails, Spacious Lake Home near Ladysmith, with a private dock on the Dairyland Flowage!, Whispering Pines Hideaway overlooking peaceful Lake Gurno!, Cozy Lake Home in Woods Near Hayward! Close Trails, Fishing, Fun Await! , Bungalow Trail, Cozy log home on 6 acres - Hayward, Lake Hayward. Private Lakefront Within Walking Distance To Downtown Hayward

Top trending hotels in Winter

Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

Winter
When you stay at this cabin in Winter, you'll be on the waterfront and steps from Chequamegon National Forest.
Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin
Spacious Winter Retreat w/ River Access + Kayaks!

Spacious Winter Retreat w/ River Access + Kayaks!

Winter
When you stay at this vacation home in Winter, you'll be 5 minutes by car from Ojibwa State Park.
Spacious Winter Retreat w/ River Access + Kayaks!
Bears Den on the private lake

Bears Den on the private lake

Winter
When you stay at this vacation home in Winter, you'll be on the waterfront and steps from Chequamegon National Forest.
Bears Den on the private lake
Save an average of 15% on thousands of hotels when you're signed in
GREAT PLACE OPENS JULY 7

GREAT PLACE OPENS JULY 7

Park Falls
When you stay at this cabin in Winter, you'll be on the waterfront and steps from Flambeau River.
GREAT PLACE OPENS JULY 7
Don't see what you're looking for?
See all available properties in Winter
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.