Book Holiday Homes in Winter

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Winter

Wooded Lakefront Home: Nestled in the natural beauty of Birchwood, Wisconsin

Wooded Lakefront Home: Nestled in the natural beauty of Birchwood, Wisconsin

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 ...
Wooded Lakefront Home: Nestled in the natural beauty of Birchwood, Wisconsin
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!
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
Save an average of 15% on thousands of hotels when you're signed in
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
Lakefront Hayward Home w/ Game Room & Private Dock

Lakefront Hayward Home w/ Game Room & Private Dock

Hayward
Located in Hayward, this vacation home is on the waterfront, within a 15-minute drive of Glover Lake and Hunter Townhall.
Lakefront Hayward Home w/ Game Room & Private Dock
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!
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, a 4-minute drive from Tiger Cat Flowage and 6 minutes from Spider Lake Townhall.
Secluded 4-season cabin w/private waterfront, epic game room & mins from trails
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.

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
107 Holiday Homes
Lowest Price
AU$244
Highest Price
AU$244
Popular accommodation
Wooded Lakefront Home: Nestled in the natural beauty of Birchwood, Wisconsin, Spacious Winter Retreat w/ River Access + Kayaks!, 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, Lakefront Hayward Home w/ Game Room & Private Dock, Scooter's Landing in Hinton Bay on Round Lake, the view is amazing!, Secluded 4-season cabin w/private waterfront, epic game room & mins from trails

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!
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
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
Save an average of 15% on thousands of hotels when you're signed in
Holiday Inn Express & Suites Hayward, an IHG Hotel

Holiday Inn Express & Suites Hayward, an IHG Hotel

2.5 out of 5
15586 County Road B, Hayward, WI
Fully refundable
The price is AU$244 per night from 1 Jan to 2 Jan
AU$244
includes taxes & fees
1 Jan - 2 Jan 2025
Holiday Inn Express & Suites Hayward, an IHG Hotel is centrally located in Hayward, a 4-minute walk from Hayward Lake and 10 minutes by foot from National Fresh ...
Holiday Inn Express & Suites Hayward, an IHG Hotel
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.