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

Executive Custom Log Lodge on Little Round Lake

500' Lakeshore, 2 Docks, Sand Beach, Sleeps 10, A/C, Pontoon Boat for Rent

Breezy Bay Beach On Round Lake

North Fork Flambeau River near Park Falls, 3BR, 1BA country home, on ATV route.

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

Lake Hayward. Private Lakefront Within Walking Distance To Downtown Hayward

Spacious 5-bedroom house in serene Clam Lake with WiFi

Private, secluded 2-bedroom house with King, Queen beds near Cable with WiFi, AC

Modern mountain- inspired monoslope home located in the beautiful Northwoods
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 | 152 Holiday Homes |
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Lowest Price | |
Highest Price | |
Popular accommodation | Executive Custom Log Lodge on Little Round Lake, 500' Lakeshore, 2 Docks, Sand Beach, Sleeps 10, A/C, Pontoon Boat for Rent, Breezy Bay Beach On Round Lake, North Fork Flambeau River near Park Falls, 3BR, 1BA country home, on ATV route., Ackwood Lodge - The Lodge, LARGE, Private Lakeshore Estate. Perfect for Family Reunions, Lake Hayward. Private Lakefront Within Walking Distance To Downtown Hayward, Spacious 5-bedroom house in serene Clam Lake with WiFi, Private, secluded 2-bedroom house with King, Queen beds near Cable with WiFi, AC, Modern mountain- inspired monoslope home located in the beautiful Northwoods |
Top trending hotels in Winter

Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.

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

Amazing Sunsets, Peaceful, Well Maintained Lake home on Beautiful, Barker lake
More ways to explore Winter
Top picks
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.