Winter Holiday Rentals

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Our top choices for Winter holiday rentals

8.8 out of 10, Excellent, (8)
"Quiet resort. I really enjoyed spending time with my family and just getting away for a week."
United States
Shelli H.
The price is AU$210
includes taxes & fees
24 Dec - 25 Dec
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
10.0 out of 10, Exceptional, (13)
"Very cozy, perfect for a family. Had everything we needed. "
United States
Erica C.
The price is AU$301
includes taxes & fees
22 Dec - 23 Dec
Charming 2-bedroom house located in Ojibwa WI just off the Tuscobia Trail.
9.4 out of 10, Exceptional, (10)
"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$233
includes taxes & fees
20 Dec - 21 Dec
Red Pines - Elk Lake #6A | Studio, 1 Bath
9.8 out of 10, Exceptional, (19)
"Amazing place to stay! So convenient and affordable, always a pleasure to stay😊"
United States
Hannah
The price is AU$234
includes taxes & fees
20 Dec - 21 Dec
Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails.
3.0 star property
8.0 out of 10, Very good, (4)
"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$347
includes taxes & fees
20 Dec - 21 Dec
Cozy home in Wisconsin's recreational northwoods.
2.0 star property
10.0 out of 10, Exceptional, (2)
"Booked this place for me and my girlfriend to get away, relax, and recharge after the holidays. This Cozy Cottage was just the thing. We had a fantastic time and everything was as advertised. Would recommend this place to anyone looking to visit the Ladysmith, WI area."
United States
Jesse K.
The price is AU$381
includes taxes & fees
20 Dec - 21 Dec
Ladysmith Cozy Cottage - Copper Tub - Waterfront
9.4 out of 10, Exceptional, (22)
"Very nice place enjoyed family time"
United States
Cheryl B.
The price is AU$345
includes taxes & fees
28 Dec - 29 Dec
Lakefront cottage w/ convenient access to restaurants, atv and snowmobile trails
3.5 star property
9.0 out of 10, Wonderful, (316)
"Colors of the trees were beautiful, staff helpful, trails plentiful and walkable."
United States
Kenneth
The price is AU$471
includes taxes & fees
22 Dec - 23 Dec
Telemark Northwoods Lodging
10.0 out of 10, Exceptional, (1)
"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 AU$318
includes taxes & fees
15 Jan - 16 Jan 2026
Red Pines - Elk Lake Condo #4 | 2 Bed, 1 Bath

Apartment in Hunter

Chip-Wa Lodging Room 1
10.0 out of 10, Exceptional, (2)
"Enjoyed our stay. Cozy and quaint."
United States
Thane B.
The price is AU$249
includes taxes & fees
20 Dec - 21 Dec
Chip-Wa Lodging Room 1
1.0 star property
The price is AU$107
includes taxes & fees
20 Dec - 21 Dec
Rustic campground in Butternut
10.0 out of 10, Exceptional, (13)
"Fantastic Place !!!!!! It was great and exactly what we needed!"
United States
Ryan
The price is AU$318
includes taxes & fees
20 Dec - 21 Dec
Red Pines - Elk Lake Condo #1 | 3 Bedroom, 1.5 Bath
9.6 out of 10, Exceptional, (4)
"We loved the house. It was exactly as pictured and described. The view was amazing. We sat on the dock one of the evenings we were there and watched the sunset. Beautiful! The house was very clean and well stocked with things we needed. "
United States
Kerri S.
The price is AU$817
includes taxes & fees
5 Jan - 6 Jan 2026
Lakefront Cabin on LCO - The Sunset Escape
10.0 out of 10, Exceptional, (75)
"Amazing property right on the lake.100% worth staying there"
United States
Adam M.
The price is AU$481
includes taxes & fees
21 Dec - 22 Dec
Blissful cozy, year round, lakeside cabin on Butternut Lake. Dogs welcome.

Holiday Home in Ladysmith

Wiggle Weigel Lodges
9.6 out of 10, Exceptional, (4)
"Nice quiet area in a good location."
United Kingdom
Jeff R.
The price is AU$592
includes taxes & fees
20 Dec - 21 Dec
Wiggle Weigel Lodges
9.8 out of 10, Exceptional, (29)
"Wonderful accommodations. Great spot for a quick getaway!"
United States
Joe B.
The price is AU$413
includes taxes & fees
21 Dec - 22 Dec
Motorsports Basecamp near lakes and forest
10.0 out of 10, Exceptional, (8)
"Excellent property, exceptional hosts. "
United States
Michael H.
The price is AU$546
includes taxes & fees
28 Dec - 29 Dec
Lake Front Cabin, Media/Game Room, Connects to Trails--NEWLY REMODELED
8.8 out of 10, Excellent, (27)
"Absolutely wonderful stay, very cabin like and rustic. Wished the TV worked for the kids at night, other than that, it was a great stay. "
United States
Crystal
The price is AU$210
includes taxes & fees
20 Dec - 21 Dec
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
9.4 out of 10, Exceptional, (22)
"This is an older resort, filled with memories, whether you were at this resort or any other in years past. Everything was sparkling clean, and all of our needs were met, except for WiFi access. We drove to a restaurant to get a net connection, but the resort proprietors did not see our message until after we left the restaurant, so we still had zero internet access, while staying there. Point: clarify net access BEFORE you arrive. "
United States
cheryl
The price is AU$210
includes taxes & fees
20 Dec - 21 Dec
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
9.6 out of 10, Exceptional, (5)
"We enjoyed our stay very much. Nice deck to sit and enjoy the outdoors. Very peaceful looking at the trees out back."
United States
Carol D.
The price is AU$351
includes taxes & fees
21 Dec - 22 Dec
Rock Garden Wisconsin Concrete Park | 3 Beds, comfortable and clean
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$413 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. 

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.

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. Barker Lake and Fishtrap 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.