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

Search Vacation Homes in Winter

  • 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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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

Kavanagh Bay Resort|Hot Tub&Sauna #1
Hayward
7.2 out of 10, Good, (5 reviews)
"This host was amazing! The house was clean and exactly what we were looking for. The hot tub was warm and an awesome way to relax after a long day of snowmobiling. We definitely look forward to staying here again!!"
United States
Chelsie H.
The price is ￥26,085
￥91,629 total
includes taxes & fees
Oct 4 - Oct 5
Kavanagh Bay Resort|Hot Tub&Sauna #1
Private kitchen

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

Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails.
Hawkins
10.0 out of 10, Exceptional, (29 reviews)
"Great hosts and location. "
United States
Paul H.
The price is ￥19,754
￥24,176 total
includes taxes & fees
Oct 3 - Oct 4
Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails.
A living room with a wooden floor, a television mounted on the wall, a desk with a chair, a sofa, and a lamp.

3. Cozy home in Wisconsin's recreational northwoods.

Cozy home in Wisconsin's recreational northwoods.
Butternut
7.6 out of 10, Good, (5 reviews)
"Weather was hot, fishing was difficult at best, we had a good time."
United States
Robert
The price is ￥17,383
￥36,680 total
includes taxes & fees
Oct 3 - Oct 4
Cozy home in Wisconsin's recreational northwoods.
Interior

4. Ultimate Hayward Trailhead Cabin

Ultimate Hayward Trailhead Cabin
Hayward
The price is ￥24,890
￥49,462 total
includes taxes & fees
Oct 19 - Oct 20
Ultimate Hayward Trailhead Cabin
A spacious room with a large dining table, leather seating, and large windows offering a view.

5. The Blue Musky Golf, UTV & Snowmobile Escape

The Blue Musky Golf, UTV & Snowmobile Escape
Hayward
10.0 out of 10, Exceptional, (23 reviews)
"Great spot right on the course, deck was a great spot to reminisce about the rounds"
United States
Jacob B.
The price is ￥21,895
￥83,797 total
includes taxes & fees
Oct 8 - Oct 9
The Blue Musky Golf, UTV & Snowmobile Escape
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.

6. Lakefront Cabin on LCO - The Sunset Escape

Lakefront Cabin on LCO - The Sunset Escape
Hayward
9.0 out of 10, Wonderful, (8 reviews)
"Very comfortable and great view of the lake."
United States
Jeffrey T.
The price is ￥37,719
￥92,922 total
includes taxes & fees
Nov 2 - Nov 3
Lakefront Cabin on LCO - The Sunset Escape
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winter Hotel Reviews

Timber Inn

Timber Inn

10/10 Excellent
"Staff was nice and helpful"
Angellee 7-night trip
Posted 3 days ago
Timber Inn

Find out more about Winter

Winter Vacation Homes information

Number of reviews
57
Accommodation
176 Vacation Homes
Lowest Price
￥24,176
Highest Price
￥92,922