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

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, (321 reviews)
"Great location for a fun Telemark event weekend."
United States
Ruth
The price is NZ$575
includes taxes & fees
12 July - 13 July
Telemark Northwoods Lodging

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 NZ$269
includes taxes & fees
5 July - 6 July
Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails.

Lunar Lodge on Windfall Lake

Lunar Lodge on Windfall Lake
Exeland
Lunar Lodge on Windfall Lake

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 NZ$408
includes taxes & fees
11 July - 12 July
Cozy home in Wisconsin's recreational northwoods.

Granny's Nest

Granny's Nest
Conrath
The price is NZ$322
includes taxes & fees
6 July - 7 July
Granny's Nest

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 NZ$415
includes taxes & fees
7 July - 8 July
Red Pines - Elk Lake Efficiency #6A

Rustic campground in Butternut

Rustic campground in Butternut
Butternut
The price is NZ$120
includes taxes & fees
5 July - 6 July
Rustic campground in Butternut

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 NZ$473
includes taxes & fees
7 July - 8 July
Lakefront cottage w/ convenient access to restaurants, atv and snowmobile trails

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 NZ$1,002
includes taxes & fees
1 Aug - 2 Aug
Northwoods Escape: Lakeside Retreat w/ Deck

Chip-Wa Lodging Room 4

Chip-Wa Lodging Room 4
Hunter
The price is NZ$286
includes taxes & fees
9 July - 10 July
Chip-Wa Lodging Room 4

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 NZ$1,001
includes taxes & fees
5 July - 6 July
Kavanagh Bay Resort|Hot Tub&Sauna #1

Northwoods Escape: Lakeside Retreat w/ Deck

Northwoods Escape: Lakeside Retreat w/ Deck
3.0 star property
Stone Lake
The price is NZ$1,003
includes taxes & fees
1 Aug - 2 Aug
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 NZ$1,286
includes taxes & fees
14 July - 15 July
Lakefront Cabin on LCO - The Sunset Escape

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 NZ$2,178
includes taxes & fees
7 July - 8 July
The Red Walleye: A Big Home on Big Fish Golf Course - Sleeps 22!

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.
The price is NZ$1,326
includes taxes & fees
7 July - 8 July
Secluded Riverfront Cabin | Hot Tub + Starlink

15min to trailhead, King Bed, PacMan

15min to trailhead, King Bed, PacMan
Hayward
9.6 out of 10, Exceptional, (12 reviews)
"It was a good long weekend the stay was enjoyable with good neighbors and relaxing accommodations "
United States
Kevin K.
The price is NZ$1,162
includes taxes & fees
28 July - 29 July
15min to trailhead, King Bed, PacMan

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 NZ$527
includes taxes & fees
6 July - 7 July
Red Pines - Elk Lake Condo #1

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.
The price is NZ$2,128
includes taxes & fees
15 July - 16 July
Lake Cabin · Hot Tub · Fire Pit · EV

Red Pines - Elk Lake Condo #2

Red Pines - Elk Lake Condo #2
Phillips
10.0 out of 10, Exceptional, (3 reviews)
"Great location"
United States
Sara S.
The price is NZ$527
includes taxes & fees
6 July - 7 July
Red Pines - Elk Lake Condo #2

Red Pines - Elk Lake Condo #4

Red Pines - Elk Lake Condo #4
Phillips
10.0 out of 10, Exceptional, (3 reviews)
"We had a very short stay but it was great from check-in to check-out. Great communication, extremely clean and very cozy. A true Northwoods experience!"
United States
Rachel K.
The price is NZ$527
includes taxes & fees
6 July - 7 July
Red Pines - Elk Lake Condo #4
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 favorite 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 depends 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 NZ$575 per night. Entering your travel dates in the search wizard you might find 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. 

Explore a world of travel with Expedia

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?

Bears Den on the private lake: This highly rated holiday home rental in Winter is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Winter?

Choose from 12 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 Black Dan 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.