Book Holiday Homes in Winter

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Featured Holiday Homes in Winter

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.
500' Lakeshore, 2 Docks, Sand Beach, Sleeps 10, A/C, Pontoon Boat for Rent
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.
Ackwood Lodge - The Lodge, LARGE, Private Lakeshore Estate. Perfect for Family Reunions
Club Suite Recreational Retreat

Club Suite Recreational Retreat

Ojibwa
Located in Ojibwa, this vacation home is on the waterfront, a 1-minute drive from Ojibwa State Park and 8 minutes from Doc Smith Park.
Club Suite Recreational Retreat
Save an average of 15% on thousands of hotels when you're signed in
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!
Lakeshore Pines | Peaceful, Lakefront Seclusion | 2 Bedroom

Lakeshore Pines | Peaceful, Lakefront Seclusion | 2 Bedroom

Butternut
Located in Butternut, this vacation home is on the waterfront, within a 10-minute drive of Flambeau Hospital and Flambeau River.
Lakeshore Pines | Peaceful, Lakefront Seclusion | 2 Bedroom
Northwood's Fish Haven on Beautiful Moose Lake; 2 kayaks, Lilly pad & game-room

Northwood's Fish Haven on Beautiful Moose Lake; 2 kayaks, Lilly pad & game-room

Hayward
When you stay at this vacation home in Hayward, you'll be on the waterfront and steps from Chequamegon National Forest.
Northwood's Fish Haven on Beautiful Moose Lake; 2 kayaks, Lilly pad & game-room
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.
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
Located in Park Falls, this vacation home is on the waterfront, within a 15-minute drive of Flambeau River and Flambeau Hospital.
North Fork Flambeau River near Park Falls, 3BR, 1BA country home, on ATV route.
Paradise Shores & Fish Galore ~private small beach & dock!

Paradise Shores & Fish Galore ~private small beach & dock!

Cable
When you a stay at this vacation home in Cable, you'll be on the waterfront, just steps from Lake Namakagon and Chequamegon National Forest.
Paradise Shores & Fish Galore ~private small beach & dock!
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.

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
150 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
500' Lakeshore, 2 Docks, Sand Beach, Sleeps 10, A/C, Pontoon Boat for Rent, Ackwood Lodge - The Lodge, LARGE, Private Lakeshore Estate. Perfect for Family Reunions, Club Suite Recreational Retreat, Little house in the woods but only 5 minutes from town!, Lakeshore Pines | Peaceful, Lakefront Seclusion | 2 Bedroom, Northwood's Fish Haven on Beautiful Moose Lake; 2 kayaks, Lilly pad & game-room, 6 bedroom 3- bath 16 people capacity pontoon included in Winter Wis., North Fork Flambeau River near Park Falls, 3BR, 1BA country home, on ATV route., Paradise Shores & Fish Galore ~private small beach & dock!

Top trending hotels in Winter

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 .
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!
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
Save an average of 15% on thousands of hotels when you're signed in
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.
Don't see what you're looking for?
See all available properties in Winter
View all properties
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.