Book Holiday Homes in Winter

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Featured Holiday Homes in Winter

New cabin on Lac Courte Oreilles!!

New cabin on Lac Courte Oreilles!!

Hayward
With a stay at this vacation home in Hayward (Northwoods Beach), you'll be steps from Lac Courte Oreilles and a 4-minute drive from Grindstone Lake.
New cabin on Lac Courte Oreilles!!
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 Hines Park.
North Fork Flambeau River near Park Falls, 3BR, 1BA country home, on ATV route.
Northwood's Fish Haven on Beautiful Moose Lake; 2 kayaks, Lilly pad & game-room

Northwood's Fish Haven on Beautiful Moose Lake; 2 kayaks, Lilly pad & game-room

Hayward
When you stay at this vacation home in Hayward, you'll be on the waterfront and steps from Chequamegon National Forest.
Northwood's Fish Haven on Beautiful Moose Lake; 2 kayaks, Lilly pad & game-room
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5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.

5 bedroom 3- bath 8 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 ...
5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.
Spruce Haven on Round Lake - Summer 2025 weeks available

Spruce Haven on Round Lake - Summer 2025 weeks available

Hayward
Located in Hayward, this vacation home is near the bay, a 1-minute drive from Round Lake and 9 minutes from Sevenwinds Casino.
Spruce Haven on Round Lake - Summer 2025 weeks available
Birch Haven Log Cabin on Spider Lake! ATV/UTV Trail with Private Dock

Birch Haven Log Cabin on Spider Lake! ATV/UTV Trail with Private Dock

Clam Lake
When you a stay at this vacation home in Mellen, you'll be on the waterfront, just steps from Chequamegon National Forest and Spider Lake.
Birch Haven Log Cabin on Spider Lake! ATV/UTV Trail with Private Dock
Birchwood Haven-Wooded Lakefront Cabin Retreat on Big Chetac Lake, Birchwood WI

Birchwood Haven-Wooded Lakefront Cabin Retreat on Big Chetac Lake, Birchwood WI

Birchwood
With a stay at this vacation home in Birchwood, you'll be on the waterfront, just steps from Lake Chetac and a 3-minute drive from Benson Creek State Wildlife ...
Birchwood Haven-Wooded Lakefront Cabin Retreat on Big Chetac Lake, Birchwood WI
Cozy new cabin on Lac Courte Oreilles!!

Cozy new cabin on Lac Courte Oreilles!!

Hayward
With a stay at this vacation home in Hayward (Northwoods Beach), you'll be steps from Lac Courte Oreilles and a 4-minute drive from Grindstone Lake.
Cozy new cabin on Lac Courte Oreilles!!
Paradise on the Pixley

Paradise on the Pixley

Park Falls
Located in Park Falls, this vacation home is on the waterfront, within a 15-minute drive of Fred Smith's Wisconsin Concrete Park and St Croix Rod Company.
Paradise on the Pixley
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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
154 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
New cabin on Lac Courte Oreilles!!, North Fork Flambeau River near Park Falls, 3BR, 1BA country home, on ATV route., Northwood's Fish Haven on Beautiful Moose Lake; 2 kayaks, Lilly pad & game-room, 5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis., Spruce Haven on Round Lake - Summer 2025 weeks available, Birch Haven Log Cabin on Spider Lake! ATV/UTV Trail with Private Dock, Birchwood Haven-Wooded Lakefront Cabin Retreat on Big Chetac Lake, Birchwood WI, Cozy new cabin on Lac Courte Oreilles!!, Paradise on the Pixley

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 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
EAGLE LODGE - Cozy Cabin Overlooking the Beautiful E. Fork of the Chippewa River

EAGLE LODGE - Cozy Cabin Overlooking the Beautiful E. Fork of the Chippewa River

Loretta
Located in Winter, this cabin is a 1-minute drive from Chequamegon National Forest and 8 minutes from Fishtrap Lake.
EAGLE LODGE - Cozy Cabin Overlooking the Beautiful E. Fork of the Chippewa River
Vintage log cabin located in the Chequamegon National Forest on Blaisdell Lake.

Vintage log cabin located in the Chequamegon National Forest on Blaisdell Lake.

Loretta
Located in Winter, this cabin is within a 15-minute drive of Chequamegon National Forest and Fishtrap Lake.
Vintage log cabin located in the Chequamegon National Forest on Blaisdell Lake.
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AmericInn by Wyndham Ladysmith

AmericInn by Wyndham Ladysmith

2.5 out of 5
800 College Ave W, Ladysmith, WI
Fully refundableReserve now, pay when you stay
Located in Ladysmith, AmericInn by Wyndham Ladysmith is within a 5-minute drive of Memorial Park and The Tee-Away Golf Course and Supper Club.
AmericInn by Wyndham 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.