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
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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 $233
CA $811 total
includes taxes & fees
Sep 27 - Sep 28
Kavanagh Bay Resort|Hot Tub&Sauna #1
A wooden staircase leading to a deck with a house in the background.

2. Motorsports Basecamp near lakes and forest

Motorsports Basecamp near lakes and forest
Hayward
9.8 out of 10, Exceptional, (33 reviews)
"The place was clean and we enjoyed our stay. "
United States
Chris P.
The price is CA $177
CA $382 total
includes taxes & fees
Sep 30 - Oct 1
Motorsports Basecamp near lakes and forest

3. 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 CA $177
CA $216 total
includes taxes & fees
Sep 28 - Sep 29
Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails.

4. Ultimate Hayward Trailhead Cabin

Ultimate Hayward Trailhead Cabin
Hayward
The price is CA $212
CA $429 total
includes taxes & fees
Sep 28 - Sep 29
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 CA $221
CA $787 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 CA $347
CA $843 total
includes taxes & fees
Sep 28 - Sep 29
Lakefront Cabin on LCO - The Sunset Escape
A living room with a wooden floor, a television mounted on the wall, a desk with a chair, a sofa, and a lamp.

7. 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 $156
CA $328 total
includes taxes & fees
Sep 28 - Sep 29
Cozy home in Wisconsin's recreational northwoods.
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

8/10 Good
"New owners have remarkable turn things around looking pretty good after a lot of clean up"
Ron 1-night trip
Posted 4 days ago
Timber Inn

Find out more about Winter

Winter Vacation Homes information

Number of reviews
90
Accommodation
176 Vacation Homes
Lowest Price
CA $216
Highest Price
CA $843

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