Holiday Rentals in Winter

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Our top choices for Winter holiday rentals

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

2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
Hayward
9.4 out of 10, Exceptional, (22 reviews)
"Cabin was clean. Everything 2 guys needed for a few days fishing."
United States
Tom N.
The price is €119
includes taxes & fees
17 Feb - 18 Feb
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage

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 to stay when I’m in the area and great hosts. "
United States
Paul H.
The price is €133
includes taxes & fees
17 Feb - 18 Feb
Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails.

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)
"Very cozy, perfect for a family. Had everything we needed. "
United States
Erica C.
The price is €166
includes taxes & fees
18 Feb - 19 Feb
Charming 2-bedroom house located in Ojibwa WI just off the Tuscobia Trail.

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)
"The host was accommodating and friendly. The place was clean and had gorgeous views of the lake. "
United States
Mary U.
The price is €270
includes taxes & fees
17 Feb - 18 Feb
Blissful cozy, year round, lakeside cabin on Butternut Lake. Dogs welcome.

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, (26 reviews)
"Very nice place enjoyed family time"
United States
Cheryl B.
The price is €139
includes taxes & fees
17 Feb - 18 Feb
Lakefront cottage w/ convenient access to restaurants, atv and snowmobile trails

Red Pines - Elk Lake Condo #1

Red Pines - Elk Lake Condo #1
Phillips
10.0 out of 10, Exceptional, (14 reviews)
"Fantastic Place !!!!!! It was great and exactly what we needed!"
United States
Ryan
Red Pines - Elk Lake Condo #1

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 €303
includes taxes & fees
17 Feb - 18 Feb
Modern Cabin with Classic Northwoods Experience...Close to Trails

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 €141
includes taxes & fees
1 Mar - 2 Mar
Chip-Wa Lodging Room 6

Rustic campground in Butternut

Rustic campground in Butternut
Butternut
The price is €62
includes taxes & fees
17 Feb - 18 Feb
Rustic campground in Butternut

Telemark Northwoods Lodging

Telemark Northwoods Lodging
3.5 star property
Cable
9.0 out of 10, Wonderful, (316 reviews)
"Perfect lodging option in a wonderful location."
United States
Jason
The price is €284
includes taxes & fees
23 Feb - 24 Feb
Telemark Northwoods Lodging

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 €177
includes taxes & fees
17 Feb - 18 Feb
Cozy home in Wisconsin's recreational northwoods.

Secluded Cabin w/Fresh Snow-Hot Tub, WIFI, King

Secluded Cabin w/Fresh Snow-Hot Tub, WIFI, King
Ojibwa
10.0 out of 10, Exceptional, (46 reviews)
"We loved how remote this cabin was, it was so quiet and beautiful. We loved the property and the cabin was very clean and comfortable. Would definitely recommend if you’re looking for a lively stay in the woods. "
United States
Laura G.
Secluded Cabin w/Fresh Snow-Hot Tub, WIFI, King

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

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 €452
includes taxes & fees
4 Mar - 5 Mar
Lakefront Cabin on LCO - The Sunset Escape

Rock Garden Rental next to Wisconsin Concrete Park

Rock Garden Rental next to Wisconsin Concrete Park
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 €300
includes taxes & fees
16 Mar - 17 Mar
Rock Garden Rental next to Wisconsin Concrete Park

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

2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
Hayward
9.0 out of 10, Wonderful, (29 reviews)
"The owner was awesome, had the cabin ready for us. Gave him my eta he had cabin warming already, beds were comfortable, near the trails. We all enjoyed our visit and planning to go back before end of the snowmobile season."
United States
Henry
The price is €119
includes taxes & fees
12 Mar - 13 Mar
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage

Lady Lake Retreat on Cavanaugh Bay w/Hot Tub&Sauna

Lady Lake Retreat on Cavanaugh Bay w/Hot Tub&Sauna
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.
Lady Lake Retreat on Cavanaugh Bay w/Hot Tub&Sauna

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 €291
includes taxes & fees
1 Mar - 2 Mar
Lake Front Cabin, Media/Game Room, Connects to Trails--NEWLY REMODELED

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

2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
Hayward
8.6 out of 10, Excellent, (9 reviews)
"Quiet resort. I really enjoyed spending time with my family and just getting away for a week."
United States
Shelli H.
The price is €119
includes taxes & fees
17 Feb - 18 Feb
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage

Time to Hideout in Hayward! BIRKIE WEEKEND STILL OPEN!

Time to Hideout in Hayward! BIRKIE WEEKEND STILL OPEN!
Hayward
The price is €410
includes taxes & fees
1 Mar - 2 Mar
Time to Hideout in Hayward! BIRKIE WEEKEND STILL OPEN!
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, apart-hotels, 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 €139 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?

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 Amazing Sunsets, Peaceful, Well Maintained Lake home on Beautiful, Barker lake as a favourite home for rent in Winter.

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 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.