Winter Holiday Rentals

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Our top choices for Winter holiday rentals

Charming 2-bedroom house located in Ojibwa WI just off the Tuscobia Trail.

Charming 2-bedroom house located in Ojibwa WI just off the Tuscobia Trail.
Ojibwa
10.0 out of 10, Exceptional, (13 reviews)
"Clean and comfortable. "
United States
Shirley N.
The price is AU$281
includes taxes & fees
4 Feb - 5 Feb
Charming 2-bedroom house located in Ojibwa WI just off the Tuscobia Trail.

2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage

2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
Hayward
8.8 out of 10, Excellent, (27 reviews)
"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$199
includes taxes & fees
3 Feb - 4 Feb
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage

Red Pines - Elk Lake #6A | Studio, 1 Bath

Red Pines - Elk Lake #6A | Studio, 1 Bath
Phillips
9.4 out of 10, Exceptional, (10 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$221
includes taxes & fees
4 Feb - 5 Feb
Red Pines - Elk Lake #6A | Studio, 1 Bath

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, (25 reviews)
"Very nice place enjoyed family time"
United States
Cheryl B.
The price is AU$242
includes taxes & fees
4 Feb - 5 Feb
Lakefront cottage w/ convenient access to restaurants, atv and snowmobile trails

Chip-Wa Lodging Room 1

Chip-Wa Lodging Room 1
Hunter
10.0 out of 10, Exceptional, (2 reviews)
"Enjoyed our stay. Cozy and quaint."
United States
Thane B.
The price is AU$237
includes taxes & fees
5 Feb - 6 Feb
Chip-Wa Lodging Room 1

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
9.8 out of 10, Exceptional, (20 reviews)
"Great place, location and hosts!"
United States
Paul H.
The price is AU$223
includes taxes & fees
3 Feb - 4 Feb
Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails.

Modern Cabin with Classic Northwoods Experience...Close to Trails

Modern Cabin with Classic Northwoods Experience...Close to Trails
Hayward
10.0 out of 10, Exceptional, (35 reviews)
"Absolutely stunning views, abundant wildlife, and peaceful. Would definitely recommend to anyone trying to escape! "
United States
Lily T.
The price is AU$534
includes taxes & fees
17 Feb - 18 Feb
Modern Cabin with Classic Northwoods Experience...Close to Trails

Telemark Northwoods Lodging

Telemark Northwoods Lodging
3.5 star property
Cable
9.0 out of 10, Wonderful, (316 reviews)
"Colors of the trees were beautiful, staff helpful, trails plentiful and walkable."
United States
Kenneth
The price is AU$484
includes taxes & fees
3 Feb - 4 Feb
Telemark Northwoods Lodging

The Bunkhouse, cozy studio in adorable Ladysmith. Escape to the Northwoods!

The Bunkhouse, cozy studio in adorable Ladysmith. Escape to the Northwoods!
Ladysmith
10.0 out of 10, Exceptional, (1 review)
"Great place to stay at. Host was accommodating. It was clean and cozy. I would book again"
United States
Nathan H.
The price is AU$215
includes taxes & fees
4 Feb - 5 Feb
The Bunkhouse, cozy studio in adorable Ladysmith. Escape to the Northwoods!

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$302
includes taxes & fees
2 Mar - 3 Mar
Cozy home in Wisconsin's recreational northwoods.

Blissful cozy, year round, lakeside cabin on Butternut Lake. Dogs welcome.

Blissful cozy, year round, lakeside cabin on Butternut Lake. Dogs welcome.
Butternut
10.0 out of 10, Exceptional, (76 reviews)
"Excellent stay. Loved the cabin. Very cutely decorated and clean. Host was very nice. "
United States
Rebecca P.
The price is AU$457
includes taxes & fees
3 Feb - 4 Feb
Blissful cozy, year round, lakeside cabin on Butternut Lake. Dogs welcome.

Lakefront Cabin on LCO - The Sunset Escape

Lakefront Cabin on LCO - The Sunset Escape
Hayward
9.6 out of 10, Exceptional, (4 reviews)
"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$710
includes taxes & fees
10 Feb - 11 Feb
Lakefront Cabin on LCO - The Sunset Escape

Red Pines - Elk Lake Condo #2 | 2 Bed, 1 Bath

Red Pines - Elk Lake Condo #2 | 2 Bed, 1 Bath
Phillips
10.0 out of 10, Exceptional, (2 reviews)
"This place was perfect for my stay. It was very clean, in a great location, and the property manager was very helpful."
United States
Andrew G.
The price is AU$300
includes taxes & fees
6 Feb - 7 Feb
Red Pines - Elk Lake Condo #2 | 2 Bed, 1 Bath

Red Pines - Elk Lake Condo #1 | 3 Bedroom, 1.5 Bath

Red Pines - Elk Lake Condo #1 | 3 Bedroom, 1.5 Bath
Phillips
10.0 out of 10, Exceptional, (13 reviews)
"Fantastic Place !!!!!! It was great and exactly what we needed!"
United States
Ryan
The price is AU$300
includes taxes & fees
3 Feb - 4 Feb
Red Pines - Elk Lake Condo #1 | 3 Bedroom, 1.5 Bath

Motorsports Basecamp near lakes and forest

Motorsports Basecamp near lakes and forest
Hayward
9.8 out of 10, Exceptional, (31 reviews)
"Wonderful accommodations. Great spot for a quick getaway!"
United States
Joe B.
The price is AU$388
includes taxes & fees
3 Feb - 4 Feb
Motorsports Basecamp near lakes and forest

Rock Garden Wisconsin Concrete Park | 3 Beds, comfortable and clean

Rock Garden Wisconsin Concrete Park | 3 Beds, comfortable and clean
Phillips
9.8 out of 10, Exceptional, (6 reviews)
"Super clean, friendly and great communication with property owner! "
United States
Kelly P.
The price is AU$331
includes taxes & fees
3 Feb - 4 Feb
Rock Garden Wisconsin Concrete Park | 3 Beds, comfortable and clean

Rustic campground in Butternut

Rustic campground in Butternut
Butternut
The price is AU$101
includes taxes & fees
3 Feb - 4 Feb
Rustic campground in Butternut

Lunar Lodge on Windfall Lake

Lunar Lodge on Windfall Lake
Exeland
The price is AU$674
includes taxes & fees
3 Feb - 4 Feb
Lunar Lodge on Windfall Lake

Lake Front Cabin, Media/Game Room, Connects to Trails--NEWLY REMODELED

Lake Front Cabin, Media/Game Room, Connects to Trails--NEWLY REMODELED
Hayward
10.0 out of 10, Exceptional, (8 reviews)
"Excellent property, exceptional hosts. "
United States
Michael H.
The price is AU$508
includes taxes & fees
22 Feb - 23 Feb
Lake Front Cabin, Media/Game Room, Connects to Trails--NEWLY REMODELED

Avail Christmas-Hot Tub, EV, 2 Kings

Avail Christmas-Hot Tub, EV, 2 Kings
Hayward
9.8 out of 10, Exceptional, (20 reviews)
"My husband and our four children had a wonderful stay at Acorn Shores! The hosts were incredibly informative and very responsive to any questions we had! We enjoyed use of the canoe, kayaks, and hot tub. The amenities were perfect and we'd highly recommend this property for your next vacation get away. Thanks again for a great stay! "
United States
Mercedes S.
The price is AU$1,053
includes taxes & fees
10 Feb - 11 Feb
Avail Christmas-Hot Tub, EV, 2 Kings
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$242 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?

Luxury 7,500‑Sq‑Ft Lakefront Lodge, Private Dock & Snowmobile Access: This holiday home rental outside of Winter is located on a lake, and has a fireplace, a balcony 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 can relax into your holiday with a garden and a selection of games.

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 Barker Lake are a couple of lovely local spots to get outside and enjoy nature. Black Dan Lake and Chequamegon National Forest 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.