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
Spacious Winter Retreat w/ River Access + Kayaks!
Ackwood Lodge - The Lodge, LARGE, Private Lakeshore Estate. Perfect for Family Reunions
Majestic views, classic charm, lifelong memories.
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
6 bedroom 3- bath 16 people capacity pontoon included in Winter Wis.
Scooter's Landing in Hinton Bay on Round Lake, the view is amazing!
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 |
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Lowest Price | |
Highest Price | |
Popular accommodation | Spacious Winter Retreat w/ River Access + Kayaks!, Ackwood Lodge - The Lodge, LARGE, Private Lakeshore Estate. Perfect for Family Reunions, Majestic views, classic charm, lifelong memories., 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, 6 bedroom 3- bath 16 people capacity pontoon included in Winter Wis., Scooter's Landing in Hinton Bay on Round Lake, the view is amazing! |
More accommodations in Winter
Top trending hotels in Winter
Spacious Winter Retreat w/ River Access + Kayaks!
Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin
Bears Den on the private lake
Cobblestone Hotels & Suites – Ladysmith
More ways to explore Winter
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.