Book Holiday Homes in Winter

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Featured Holiday Homes in Winter

Little house in the woods but only 5 minutes from town!

Little house in the woods but only 5 minutes from town!

Ladysmith
Located in Ladysmith, this vacation home is in a rural location, a 1-minute drive from Flambeau River and 8 minutes from Memorial Park.
Little house in the woods but only 5 minutes from town!
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.
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Sandalwood Retreat on Round Lake - Enjoy our screened porch & gorgeous sunsets 

Sandalwood Retreat on Round Lake - Enjoy our screened porch & gorgeous sunsets 

Hayward
Located in Hayward, this vacation home is on the waterfront, a 1-minute drive from Round Lake and 8 minutes from Lovejoy Lake.
Sandalwood Retreat on Round Lake - Enjoy our screened porch & gorgeous sunsets 
Renovated cabin on Lac Courte Oreilles Lake - minutes from trails!

Renovated cabin on Lac Courte Oreilles Lake - minutes from trails!

Hayward
The price is AU$593 per night from 2 Mar to 3 Mar
AU$593
includes taxes & fees
2 Mar - 3 Mar
With a stay at this vacation home in Hayward (Northwoods Beach), you'll be steps from Lac Courte Oreilles and a 5-minute drive from Grindstone Lake.
Renovated cabin on Lac Courte Oreilles Lake - minutes from trails!
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
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
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
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!
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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
AU$238
Highest Price
AU$593
Popular accommodation
Little house in the woods but only 5 minutes from town!, Mallard Manor, 6 bedroom 3- bath 16 people capacity pontoon included in Winter Wis., Sandalwood Retreat on Round Lake - Enjoy our screened porch & gorgeous sunsets , Renovated cabin on Lac Courte Oreilles Lake - minutes from trails!, Wooded Lakefront Home: Nestled in the natural beauty of Birchwood, Wisconsin, Lake Hayward. Private Lakefront Within Walking Distance To Downtown Hayward, Secluded 4-season cabin w/private waterfront, epic game room & mins from trails, Renovated Historic Church Along Namekagon River!

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!
Luxury Cabin, 800+ feet frontage, 733 acre Lake, Hot tub, Pontoon, Fireplace .

Luxury Cabin, 800+ feet frontage, 733 acre Lake, Hot tub, Pontoon, Fireplace .

Winter, Wisconsin
Located in Winter, this cabin is a 1-minute drive from Lake Winter and 8 minutes from Winter Town Hall.
Luxury Cabin, 800+ feet frontage, 733 acre Lake, Hot tub, Pontoon, Fireplace .
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
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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$238 per night from 2 Mar to 3 Mar
AU$238
includes taxes & fees
2 Mar - 3 Mar
Holiday Inn Express & Suites Hayward by IHG is centrally located in Hayward, a 4-minute walk from Hayward Lake and 10 minutes by foot from National Fresh Water ...
Holiday Inn Express & Suites Hayward, an IHG Hotel
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.

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