Book Holiday Homes in Winter

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Featured Holiday Homes in Winter

Executive Custom Log Lodge on Little Round Lake

Executive Custom Log Lodge on Little Round Lake

Hayward
Located in Hayward, this vacation home is on the waterfront, a 2-minute drive from Round Lake and 7 minutes from Lovejoy Lake.
Opens in a new windowExecutive Custom Log Lodge on Little Round Lake
500' Lakeshore, 2 Docks, Sand Beach, Sleeps 10, A/C, Pontoon Boat for Rent

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

Couderay
Located in Chief Lake, this vacation home is on the waterfront, within a 15-minute drive of Whitefish Lake and Lac Courte Oreilles.
Opens in a new window500' Lakeshore, 2 Docks, Sand Beach, Sleeps 10, A/C, Pontoon Boat for Rent
Breezy Bay Beach On Round Lake

Breezy Bay Beach On Round Lake

Hayward
Located in Hayward, this vacation home is on the waterfront, a 1-minute drive from Round Lake and 6 minutes from Sevenwinds Casino.
Opens in a new windowBreezy Bay Beach On Round Lake
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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
When you stay at this vacation home in Park Falls, you'll be on the waterfront and steps from Flambeau River.
Opens in a new windowNorth 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

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

Bass Lake
With a stay at this vacation home in Hayward, you'll be on the waterfront, just steps from Lac Courte Oreilles and a 3-minute drive from Schoolhouse Lake.
Opens in a new windowAckwood Lodge - The Lodge, LARGE, Private Lakeshore Estate. Perfect for Family Reunions
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.
Opens in a new windowLake Hayward. Private Lakefront Within Walking Distance To Downtown Hayward
Spacious 5-bedroom house in serene Clam Lake with WiFi

Spacious 5-bedroom house in serene Clam Lake with WiFi

Clam Lake
With a stay at this vacation home in Clam Lake, you'll be just steps from Chequamegon National Forest and Upper Clam Lake.
Opens in a new windowSpacious 5-bedroom house in serene Clam Lake with WiFi
Private, secluded 2-bedroom house with King, Queen beds near Cable with WiFi, AC

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

Cable
Located in Cable, this vacation home is within a 10-minute drive of The Book House and Forest Lodge Library.
Opens in a new windowPrivate, secluded 2-bedroom house with King, Queen beds near Cable with WiFi, AC
Modern mountain- inspired monoslope home located in the beautiful Northwoods

Modern mountain- inspired monoslope home located in the beautiful Northwoods

Hayward
When you stay at this vacation home in Hayward, you'll be within a 10-minute drive of Spider Lake Townhall and Round Lake.
Opens in a new windowModern mountain- inspired monoslope home located in the beautiful Northwoods
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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
152 Holiday Homes
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

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.
Opens in a new windowBucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin
5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.

5 bedroom 3- bath 8 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 ...
Opens in a new window5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.
EAGLE LODGE - Cozy Cabin Overlooking the Beautiful E. Fork of the Chippewa River

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

Loretta
Located in Winter, this cabin is a 1-minute drive from Chequamegon National Forest and 8 minutes from Fishtrap Lake.
Opens in a new windowEAGLE LODGE - Cozy Cabin Overlooking the Beautiful E. Fork of the Chippewa River
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Amazing Sunsets, Peaceful, Well Maintained  Lake home on Beautiful, Barker lake

Amazing Sunsets, Peaceful, Well Maintained Lake home on Beautiful, Barker lake

Winter
When you a stay at this vacation home in Winter, you'll be on the beach, just steps from Chequamegon National Forest and Barker Lake.
Opens in a new windowAmazing Sunsets, Peaceful, Well Maintained Lake home on Beautiful, Barker lake
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.

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^Subject to availability and chosen travel dates.