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 WI
When you stay at this vacation home in Park Falls, you'll be on the waterfront and steps from Flambeau River.
Opens in a new windowNorth Fork Flambeau River near Park Falls, 3BR, 1BA country home, on ATV route.
Sugar Maple at Hansen Lake

Sugar Maple at Hansen Lake

Park Falls WI
Located in Park Falls, this vacation home is on the waterfront, within a 15-minute drive of Flambeau Hospital and Hines Park.
Opens in a new windowSugar Maple at Hansen Lake
New cabin on Lac Courte Oreilles!!

New cabin on Lac Courte Oreilles!!

Hayward WI
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.
Opens in a new windowNew cabin on Lac Courte Oreilles!!
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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

Winter WI
When you stay at this vacation home in Winter, you'll be on the beach, just steps from Chequamegon National Forest and Barker Lake.
Opens in a new windowAmazing Sunsets, Peaceful, Well Maintained Lake home on Beautiful, Barker lake
Amazing Fall Colors, Nature, Fireplaces, Screened Porch, Secluded!

Amazing Fall Colors, Nature, Fireplaces, Screened Porch, Secluded!

Hayward WI
A stay at this vacation home places you in the heart of Hayward, a 1-minute drive from Tiger Cat Flowage and 6 minutes from Burns Lake.
Opens in a new windowAmazing Fall Colors, Nature, Fireplaces, Screened Porch, Secluded!
Cozy new cabin on Lac Courte Oreilles!!

Cozy new cabin on Lac Courte Oreilles!!

Hayward WI
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.
Opens in a new windowCozy new cabin on Lac Courte Oreilles!!
Spruce Haven on Round Lake - Summer 2026 weeks available

Spruce Haven on Round Lake - Summer 2026 weeks available

Bouvet Island
Located in Hayward, this vacation home is near the bay, a 1-minute drive from Round Lake and 9 minutes from Sevenwinds Casino.
Opens in a new windowSpruce Haven on Round Lake - Summer 2026 weeks available
Long Lake Retreat in Phillips, Wisconsin

Long Lake Retreat in Phillips, Wisconsin

Phillips WI
Located in Phillips, this vacation home is on the waterfront, a 5-minute drive from Lidice Memorial and 8 minutes from Wisconsin Concrete Park.
Opens in a new windowLong Lake Retreat in Phillips, Wisconsin
Ultimate Hayward Trailhead Cabin

Ultimate Hayward Trailhead Cabin

Hayward WI
The price is AU$382 per night from 14 May to 15 May
AU$382
14 May - 15 May
includes taxes & fees
Located in Hayward, this vacation home is in a rural location, a 1-minute drive from Round Lake and 8 minutes from Spider Lake Townhall.
Opens in a new windowUltimate Hayward Trailhead Cabin
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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
AU$382
Highest Price
AU$819
Popular accommodation
North Fork Flambeau River near Park Falls, 3BR, 1BA country home, on ATV route., Sugar Maple at Hansen Lake, New cabin on Lac Courte Oreilles!!, Amazing Sunsets, Peaceful, Well Maintained Lake home on Beautiful, Barker lake, Amazing Fall Colors, Nature, Fireplaces, Screened Porch, Secluded!, Cozy new cabin on Lac Courte Oreilles!!, Spruce Haven on Round Lake - Summer 2026 weeks available, Long Lake Retreat in Phillips, Wisconsin, Ultimate Hayward Trailhead Cabin

Top trending hotels in Winter

Amazing Sunsets, Peaceful, Well Maintained  Lake home on Beautiful, Barker lake

Amazing Sunsets, Peaceful, Well Maintained Lake home on Beautiful, Barker lake

Winter WI
When you stay at this vacation home in Winter, you'll be on the beach, just steps from Chequamegon National Forest and Barker Lake.
Opens in a new windowAmazing Sunsets, Peaceful, Well Maintained Lake home on Beautiful, Barker lake
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 WI
With a stay at this cabin in Winter, you'll be within a 15-minute drive of Fishtrap Lake and Bluegill Lake.
Opens in a new windowEAGLE LODGE - Cozy Cabin Overlooking the Beautiful E. Fork of the Chippewa River
The Lodge on Lake of the Pines - enjoy the Northwoods in comfort!

The Lodge on Lake of the Pines - enjoy the Northwoods in comfort!

Loretta WI
The price is AU$819 per night from 14 May to 15 May
AU$819
14 May - 15 May
includes taxes & fees
With a stay at this lodge in Winter, you'll be on the waterfront, and 15.5 mi (25 km) from Winter Town Hall and 16.7 mi (26.8 km) from Winter Public ...
Opens in a new windowThe Lodge on Lake of the Pines - enjoy the Northwoods in comfort!
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 WI
When you stay at this cabin in Winter, you'll be on the waterfront and steps from Flambeau River.
Opens in a new windowGREAT PLACE OPENS JULY 7
Don't see what you're looking for?
See all available properties in Winter
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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.

Top Picks

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