Winter, WI Vacation Homes from ￥24,490

A snowy landscape with a red barn and a red shed.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Winter vacation homes

An outdoor seating area with Adirondack chairs and a fire pit, surrounded by a forested landscape.

1. Kavanagh Bay Resort|Hot Tub&Sauna #1

Hayward

Erica O.

￥111,511 total

includes taxes & fees

Sep 6 - Sep 7

A wooden staircase leading to a deck with a house in the background.

2. Motorsports Basecamp near lakes and forest

Hayward

Chris P.

￥43,194 total

includes taxes & fees

Sep 1 - Sep 2

A wooden sauna with a sliding glass door, two white lanterns, and the text "sunlighters Amplify" on the glass.

3. River's Edge Tiny Home | Expansive Deck

Park Falls

Dan O.

￥62,397 total

includes taxes & fees

Sep 1 - Sep 2

4. Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails.

Hawkins

Robin

￥24,490 total

includes taxes & fees

Sep 1 - Sep 2

A cozy log cabin interior with a wooden ceiling, a ceiling fan, a large arched window, a leather sofa, a coffee table, and a small side table.

5. Lakefront Cabin on LCO - The Sunset Escape

Hayward

Jeffrey T.

￥105,948 total

includes taxes & fees

Sep 2 - Sep 3

6. Ultimate Hayward Trailhead Cabin

Hayward

￥43,847 total

includes taxes & fees

Sep 1 - Sep 2

A two-story house with a deck, large windows, and a front door.

7. Hayward Northwoods Escape -ATV Trails, Pond + Kayaks & Firepit

Hayward

￥71,782 total

includes taxes & fees

Sep 9 - Sep 10

A living room with a wooden floor, a television mounted on the wall, a desk with a chair, a sofa, and a lamp.

8. Cozy home in Wisconsin's recreational northwoods.

Butternut

Robert

￥37,664 total

includes taxes & fees

Sep 28 - Sep 29

View all properties

Find vacation rentals that suit your style

Cabins

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Top Winter Hotel Reviews

AmeriVu Inn

8/10 Good

"Very low toilet and no handicap bar in shower toilet area"

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

10/10 Excellent

"Great find! This was our second stay at this property and it once again was a good time for our 4 generation family. We noticed some additions to amenities including a second dock, a new playground set and a lounging raft. We appreciate the pontoon available for use by guests. The grill, Blackstone, and swings around the fire pit were enjoyed by all."

The Lazy River Lodge - Float, Fish & Relax on the Chippewa

10/10 Excellent

"If your looking for an amazing place away from civilization where you can relax with your family and furbabies. This is the place to go. The cabin is stunning and has lots of options. You can fish the river from the property or take the kayaks/canoe on the river. You can light a fire make some smores and have family game night with either the outside games or even inside games or you can sit on the deck and enjoy the sound of nature and the view. Our dogs were able to come and the one thing we enjoyed was even though the yard isnt "fenced" its secluded by tree and bush lines on each side of the cabin, so even though there was another dog our dogs could hear they couldn't see them, so they were able to relax and enjoy the non-stimulating environment. If your the outdoorsy type there is a lot of public walking, atv trails and beautiful falls you can enjoy. Other fun things to within an hour that we enjoyed was the Scheers lumberjack show, Great northern train ride and the shops in downtown Hayward. If you do the train ride highly recommend stopping at Strongmans brewery if you like BBQ food. If you shop downtown Hayward Anglers Bar and grill is good and before you leave check out lakewood Cafe that is in downtown winter. I was hesitant traveling almost 4 hours to the middle of nowhere with the kids and dogs worried there wouldn't be much to do, but our vacation here didnt disappoint. The kids asked if we could come back yearly they enjoyed it that much!!"

Find out more about Winter

Winter Vacation Homes information

Number of reviews	58
Accommodation	167 Vacation Homes
Lowest Price	￥24,490
Highest Price	￥111,511

Explore a world of travel with Expedia

More ways to book

Book Vacation Homes in Winter on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winter vacation homes

1. Kavanagh Bay Resort|Hot Tub&Sauna #1

2. Motorsports Basecamp near lakes and forest

3. River's Edge Tiny Home | Expansive Deck

4. Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails.

5. Lakefront Cabin on LCO - The Sunset Escape

6. Ultimate Hayward Trailhead Cabin

7. Hayward Northwoods Escape -ATV Trails, Pond + Kayaks & Firepit

8. Cozy home in Wisconsin's recreational northwoods.

Find vacation rentals that suit your style

Top Winter Hotel Reviews

AmeriVu Inn

Quality Inn Ladysmith

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

Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

Charming 2-bedroom Hayward Cabin on Lac Courte Oreilles

The Lazy River Lodge - Float, Fish & Relax on the Chippewa

Timber Inn

Luxury 7,500‑Sq‑Ft Lakefront Lodge, Private Dock & Snowmobile Access

Water's Edge Retreat on Butternut Lake!

Find out more about Winter

Winter Vacation Homes information

Explore a world of travel with Expedia

Search Vacation Homes in Winter

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winter vacation homes

1. Kavanagh Bay Resort|Hot Tub&Sauna #1

2. Motorsports Basecamp near lakes and forest

3. River's Edge Tiny Home | Expansive Deck

4. Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails.

5. Lakefront Cabin on LCO - The Sunset Escape

6. Ultimate Hayward Trailhead Cabin

7. Hayward Northwoods Escape -ATV Trails, Pond + Kayaks & Firepit

8. Cozy home in Wisconsin's recreational northwoods.

Find vacation rentals that suit your style

Top Winter Hotel Reviews

AmeriVu Inn

Find out more about Winter

Winter Vacation Homes information

Explore a world of travel with Expedia