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

Winter Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

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 CA $237
CA $747 total
includes taxes & fees
Nov 16 - Nov 17
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, (32 reviews)
"Great place, location and hosts. "
United States
Paul H.
The price is CA $178
CA $206 total
includes taxes & fees
Nov 16 - Nov 17
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 CA $166
CA $312 total
includes taxes & fees
Nov 18 - Nov 19
Cozy home in Wisconsin's recreational northwoods.
Interior

4. Ultimate Hayward Trailhead Cabin

Ultimate Hayward Trailhead Cabin
Hayward
10.0 out of 10, Exceptional, (1 review)
"My husband and I had a wonderful stay at this cabin. The pictures and description are totally accurate. The home was clean, well furnished and as comfortable as home including the beds. The kitchen was well equipped with everything we needed and the linnens were fresh, new and plush. The shower is spacious and there was plenty of hot water. The screened porch was wonderful to sit out in the afternoon and watch the leaves fall in the breeze. (We were there early October). We found lots of...
United States
Joan O.
The price is CA $214
CA $391 total
includes taxes & fees
Nov 16 - Nov 17
Ultimate Hayward Trailhead Cabin
A wooden staircase leading to a deck with a house in the background.

5. Motorsports Basecamp near lakes and forest

Motorsports Basecamp near lakes and forest
Hayward
9.8 out of 10, Exceptional, (34 reviews)
"Excellent host and accommodations."
United States
Ben S.
The price is CA $202
CA $424 total
includes taxes & fees
Nov 16 - Nov 17
Motorsports Basecamp near lakes and forest
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
9.2 out of 10, Wonderful, (9 reviews)
"Very comfortable and great view of the lake."
United States
Jeffrey T.
The price is CA $277
CA $720 total
includes taxes & fees
Nov 17 - Nov 18
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.
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Top Winter Hotel Reviews

Timber Inn

Timber Inn

10/10 Excellent
"The staff was friendly and rooms were clean. I like that it was dog friendly and having a pizza delivered from their kitchen to my room was a plus."
Eric 4-night trip
Posted 2 days ago
Timber Inn

Find out more about Winter

Winter Vacation Homes information

Number of reviews
72
Accommodation
142 Vacation Homes
Lowest Price
CA $206
Highest Price
CA $747

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