Red house after a December snow storm in Wisconsin

Winter Holiday Rentals

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Our top choices for Winter holiday rentals

Telemark Northwoods Lodging

Telemark Northwoods Lodging
3.5 star property
Cable
9.0 out of 10, Wonderful, (320 reviews)
"Great location for a fun Telemark event weekend."
United States
Ruth
The price is AU$474
includes taxes & fees
13 July - 14 July
Telemark Northwoods Lodging

Red Pines - Elk Lake Efficiency #6A

Red Pines - Elk Lake Efficiency #6A
Phillips
9.6 out of 10, Exceptional, (12 reviews)
"Quiet, peaceful place that was perfect for a weekend getaway. The room was clean and well stocked. "
United States
Karan B.
The price is AU$341
includes taxes & fees
27 June - 28 June
Red Pines - Elk Lake Efficiency #6A

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, (21 reviews)
"Great hosts and location. "
United States
Paul H.
The price is AU$224
includes taxes & fees
29 June - 30 June
Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails.

Motorsports Basecamp near lakes and forest

Motorsports Basecamp near lakes and forest
Hayward
9.8 out of 10, Exceptional, (31 reviews)
"The place was clean and we enjoyed our stay. "
United States
Chris P.
The price is AU$482
includes taxes & fees
29 June - 30 June
Motorsports Basecamp near lakes and forest

Cozy home in Wisconsin's recreational northwoods.

Cozy home in Wisconsin's recreational northwoods.
Butternut
8.0 out of 10, Very good, (4 reviews)
"Property was located just down the road from the snowmobiling trail and was easy and quick in/out access"
United States
Jake C.
The price is AU$340
includes taxes & fees
1 July - 2 July
Cozy home in Wisconsin's recreational northwoods.

Lunar Lodge on Windfall Lake

Lunar Lodge on Windfall Lake
Exeland
The price is AU$816
includes taxes & fees
29 June - 30 June
Lunar Lodge on Windfall Lake

Lakefront cottage w/ convenient access to restaurants, atv and snowmobile trails

Lakefront cottage w/ convenient access to restaurants, atv and snowmobile trails
Phillips
9.6 out of 10, Exceptional, (31 reviews)
"Very nice place to stay!"
United States
Dina A.
The price is AU$386
includes taxes & fees
29 June - 30 June
Lakefront cottage w/ convenient access to restaurants, atv and snowmobile trails

Granny's Nest

Granny's Nest
Conrath
The price is AU$268
includes taxes & fees
29 June - 30 June
Granny's Nest

Ultimate Hayward Trailhead Cabin

Ultimate Hayward Trailhead Cabin
Hayward
The price is AU$409
includes taxes & fees
28 June - 29 June
Ultimate Hayward Trailhead Cabin

Northwoods Escape: Lakeside Retreat w/ Deck

Northwoods Escape: Lakeside Retreat w/ Deck
3.0 star property
Stone Lake
The price is AU$881
includes taxes & fees
29 June - 30 June
Northwoods Escape: Lakeside Retreat w/ Deck

Lakefront Cabin w/ Pool Table+Waterfall: Northwoods Nostalgia + Modern Amenities

Lakefront Cabin w/ Pool Table+Waterfall: Northwoods Nostalgia + Modern Amenities
Clam Lake
10.0 out of 10, Exceptional, (35 reviews)
"Stayed here for a snowmobile trip. Host helped us figure out the best way to access trails and was helpful with all questions we had. Very clean and easy to access place to stay with everything we were looking for!"
United States
Colten R.
Lakefront Cabin w/ Pool Table+Waterfall: Northwoods Nostalgia + Modern Amenities

Kavanagh Bay Resort|Hot Tub&Sauna #1

Kavanagh Bay Resort|Hot Tub&Sauna #1
Hayward
10.0 out of 10, Exceptional, (1 review)
"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 AU$764
includes taxes & fees
29 June - 30 June
Kavanagh Bay Resort|Hot Tub&Sauna #1

Chip-Wa Lodging Room 6

Chip-Wa Lodging Room 6
Hunter
10.0 out of 10, Exceptional, (1 review)
"Room was very clean. Property looks well kept and price was affordable."
United States
Kathy
The price is AU$239
includes taxes & fees
7 July - 8 July
Chip-Wa Lodging Room 6

Northwoods Escape: Lakeside Retreat w/ Deck

Northwoods Escape: Lakeside Retreat w/ Deck
Stone Lake
10.0 out of 10, Exceptional, (2 reviews)
"Clean rooms for sure everything looked good. Ac was very good as well."
United States
Erik N.
The price is AU$883
includes taxes & fees
7 July - 8 July
Northwoods Escape: Lakeside Retreat w/ Deck

Lakefront Cabin on LCO - The Sunset Escape

Lakefront Cabin on LCO - The Sunset Escape
Hayward
9.6 out of 10, Exceptional, (5 reviews)
"Very comfortable and great view of the lake."
United States
Jeffrey T.
The price is AU$1,134
includes taxes & fees
14 July - 15 July
Lakefront Cabin on LCO - The Sunset Escape

Secluded Riverfront Cabin | Hot Tub + Starlink

Secluded Riverfront Cabin | Hot Tub + Starlink
Ojibwa
10.0 out of 10, Exceptional, (47 reviews)
"This cabin was a perfect fit for our family of five and our dog. Everything was clean and comfortable, and the hot tub was a highlight of our stay. The location made it easy to get on the snowmobile trails, and the hosts were wonderful to work with and very responsive."
United States
Jennifer P.
Secluded Riverfront Cabin | Hot Tub + Starlink

Rustic campground in Butternut

Rustic campground in Butternut
Butternut
The price is AU$102
includes taxes & fees
27 June - 28 June
Rustic campground in Butternut

Lake Cabin · Hot Tub · Fire Pit · EV

Lake Cabin · Hot Tub · Fire Pit · EV
Hayward
9.8 out of 10, Exceptional, (22 reviews)
"Nice cabin, great beds. Really enjoyed our time. "
United States
Katie J.
Lake Cabin · Hot Tub · Fire Pit · EV

The Red Walleye: A Big Home on Big Fish Golf Course - Sleeps 22!

The Red Walleye: A Big Home on Big Fish Golf Course - Sleeps 22!
Hayward
10.0 out of 10, Exceptional, (17 reviews)
"Wonderful property, very clean fit our needs of the group. Will definitely stay again"
United States
Kylene O.
The price is AU$1,966
includes taxes & fees
13 July - 14 July
The Red Walleye: A Big Home on Big Fish Golf Course - Sleeps 22!

Red Pines - Elk Lake Condo #1

Red Pines - Elk Lake Condo #1
Phillips
10.0 out of 10, Exceptional, (15 reviews)
"The property was just what we needed for our weekend trip. Everything was nice and clean."
United States
Tom B.
The price is AU$438
includes taxes & fees
30 June - 1 July
Red Pines - Elk Lake Condo #1
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

Find out more about Winter

Everything you need to know about Winter holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winter holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winter holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winter holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winter. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winter holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winter holiday rentals we have selected for you start as low as AU$386 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winter rentals

At Expedia, we put the best Winter holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winter rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winter holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winter. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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Frequently asked questions

Can I find a holiday rental in Winter?

Yes, there are holiday rentals close to the most popular sights in Winter, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Winter has to offer?

5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.: This highly rated holiday home rental in Winter is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. Our travellers also rate Bears Den on the private lake as a favourite home for rent in Winter.

How many holiday rentals are there in Winter?

Choose from 11 Expedia holiday rentals in Winter for a memorable holiday.

What can I see and do in Winter?

Lake Winter and Perch Lake are a couple of lovely local spots to get outside and enjoy nature. Ojibwa State Park and Barker Lake are other places to visit while you're in town.

What are holiday rentals like in Winter?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winter. Holiday rentals feature extras like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for a small group gathering.