Book Holiday Homes in Winter

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Featured Holiday Homes in Winter

Spacious Winter Retreat w/ River Access + Kayaks!

Spacious Winter Retreat w/ River Access + Kayaks!

Winter
With a stay at this vacation home in Winter, you'll be within a 15-minute drive of Ojibwa State Park and Doc Smith Park.
Spacious Winter Retreat w/ River Access + Kayaks!
Ackwood Lodge - The Lodge, LARGE, Private Lakeshore Estate. Perfect for Family Reunions

Ackwood Lodge - The Lodge, LARGE, Private Lakeshore Estate. Perfect for Family Reunions

Bass Lake
With a stay at this vacation home in Hayward, you'll be on the waterfront, just steps from Lac Courte Oreilles and a 3-minute drive from Schoolhouse Lake.
Ackwood Lodge - The Lodge, LARGE, Private Lakeshore Estate. Perfect for Family Reunions
Majestic views, classic charm, lifelong memories.

Majestic views, classic charm, lifelong memories.

Cable
When you a stay at this vacation home in Cable, you'll be on the waterfront, just steps from Lake Namakagon and Chequamegon National Forest.
Majestic views, classic charm, lifelong memories.
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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
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.
Renovated Historic Church Along Namekagon River!

Renovated Historic Church Along Namekagon River!

Hayward
When you stay at this vacation home in Hayward, you'll be within a 10-minute drive of The Book House and Forest Lodge Library.
Renovated Historic Church Along Namekagon River!
Mallard Manor

Mallard Manor

Hayward
With a stay at this vacation home in Hayward, you'll be within a 10-minute drive of Nelson Lake and Park Theater.
Mallard Manor
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
With a stay at this vacation home in Winter, you'll be on the waterfront, just a 1-minute walk from South Barber Lake and 7 minutes by foot from Barber ...
6 bedroom 3- bath 16 people capacity pontoon included in Winter Wis.
Scooter's Landing in Hinton Bay on Round Lake, the view is amazing!

Scooter's Landing in Hinton Bay on Round Lake, the view is amazing!

Hayward
Located in Hayward, this vacation home is on the waterfront, within a 15-minute drive of Round Lake and Sevenwinds Casino.
Scooter's Landing in Hinton Bay on Round Lake, the view is amazing!
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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
103 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Spacious Winter Retreat w/ River Access + Kayaks!, Ackwood Lodge - The Lodge, LARGE, Private Lakeshore Estate. Perfect for Family Reunions, Majestic views, classic charm, lifelong memories., Lake Hayward. Private Lakefront Within Walking Distance To Downtown Hayward, North Fork Flambeau River near Park Falls, 3BR, 1BA country home, on ATV route., Renovated Historic Church Along Namekagon River!, Mallard Manor, 6 bedroom 3- bath 16 people capacity pontoon included in Winter Wis., Scooter's Landing in Hinton Bay on Round Lake, the view is amazing!

Top trending hotels in Winter

Spacious Winter Retreat w/ River Access + Kayaks!

Spacious Winter Retreat w/ River Access + Kayaks!

Winter
With a stay at this vacation home in Winter, you'll be within a 15-minute drive of Ojibwa State Park and Doc Smith Park.
Spacious Winter Retreat w/ River Access + Kayaks!
Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

Winter
When you a stay at this cabin in Winter, you'll be on the waterfront, just steps from Chequamegon National Forest and Barker Lake.
Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin
Bears Den on the private lake

Bears Den on the private lake

Winter
When you a stay at this vacation home in Winter, you'll be on the waterfront, within a 5-minute walk of Chequamegon National Forest and Perch Lake.
Bears Den on the private lake
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Cobblestone Hotels & Suites – Ladysmith

Cobblestone Hotels & Suites – Ladysmith

2.5 out of 5
700 West 9th Street, Ladysmith, WI
With a stay at Cobblestone Hotels & Suites – Ladysmith in Ladysmith, you'll be within a 10-minute walk of Marshfield Medical Center - Ladysmith and Flambeau ...
Cobblestone Hotels & Suites – Ladysmith
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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.

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^Subject to availability and chosen travel dates.