Book Holiday Homes in Winter

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

Featured Holiday Homes in Winter

Spacious Winter Retreat w/ River Access + Kayaks!

Spacious Winter Retreat w/ River Access + Kayaks!

Winter
Book a stay at this family-friendly vacation home in Winter. Enjoy patios, an in-room coffeemaker, and in-room fireplaces. Popular attractions Ojibwa State Park ...
Spacious Winter Retreat w/ River Access + Kayaks!
Ackwood Lodge - The Lodge, LARGE, Private Lakeshore Estate. Perfect for Family Reunions

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

Bass Lake
Book a stay at this family-friendly vacation home in Hayward. Enjoy a garden, a pool table, and an in-room coffeemaker. Popular attractions Schoolhouse Lake ...
Ackwood Lodge - The Lodge, LARGE, Private Lakeshore Estate. Perfect for Family Reunions
Majestic views, classic charm, lifelong memories.

Majestic views, classic charm, lifelong memories.

Cable
Stay at this vacation home in Cable. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Lake Namakagon and Chequamegon National Forest ...
Majestic views, classic charm, lifelong memories.
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Lake Hayward.  Private Lakefront Within Walking Distance To Downtown Hayward

Lake Hayward. Private Lakefront Within Walking Distance To Downtown Hayward

Hayward
Book a stay at this family-friendly vacation home in Hayward. Enjoy free WiFi, a garden, and patios. Popular attractions Lumberjack Bowl and Hayward Lake are ...
Lake Hayward. Private Lakefront Within Walking Distance To Downtown Hayward
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
Stay at this vacation home in Park Falls. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Park Falls Country Club and Hines ...
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
Stay at this vacation home in Hayward. Enjoy a garden, patios, and an in-room coffeemaker. Popular attraction American Birkebeiner Trail is located nearby.
Renovated Historic Church Along Namekagon River!
Mallard Manor

Mallard Manor

Hayward
Stay at this vacation home in Hayward. Enjoy air conditioning. Popular attractions American Birkebeiner Trail and Nelson Lake are located nearby.
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
Book a stay at this family-friendly vacation home in Winter. Enjoy free WiFi, a pool table, and patios. Popular attraction Lake Chippewa is located nearby.
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!

Scooter's Landing in Hinton Bay on Round Lake, the view is amazing!

Hayward
Stay at this vacation home in Hayward. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Round Lake and Sevenwinds Casino are located ...
Scooter's Landing in Hinton Bay on Round Lake, the view is amazing!
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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
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!

Top trending hotels in Winter

Spacious Winter Retreat w/ River Access + Kayaks!

Spacious Winter Retreat w/ River Access + Kayaks!

Winter
Book a stay at this family-friendly vacation home in Winter. Enjoy patios, an in-room coffeemaker, and in-room fireplaces. Popular attractions Ojibwa State Park ...
Spacious Winter Retreat w/ River Access + Kayaks!
Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

Winter
Stay at this cabin in Winter. Enjoy an in-room coffeemaker and air conditioning. Popular attraction Lake Chippewa is located nearby.
Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin
Bears Den on the private lake

Bears Den on the private lake

Winter
Book a stay at this family-friendly vacation home in Winter. Enjoy free WiFi, a garden, and patios.
Bears Den on the private lake
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Cobblestone Hotels & Suites – Ladysmith

Cobblestone Hotels & Suites – Ladysmith

2.5 out of 5
700 West 9th Street, Ladysmith, WI
Book a stay at this business-friendly hotel in Ladysmith. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Memorial Park and The Tee-Away ...
Cobblestone Hotels & Suites – Ladysmith
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.