Winter Holiday Rentals

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Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

Our top choices for Winter holiday rentals

TV, fireplace, DVD player, books

Cabin in Hayward

2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
9.0 out of 10, Wonderful, (30 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 HK$782
HK$1,071 total
includes taxes & fees
2 Mar - 3 Mar
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
Interior

Holiday Home in Ojibwa

Charming 2-bedroom house located in Ojibwa WI just off the Tuscobia Trail.
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 HK$880
HK$1,539 total
includes taxes & fees
3 Mar - 4 Mar
Charming 2-bedroom house located in Ojibwa WI just off the Tuscobia Trail.
Fridge, microwave, oven, stovetop

Holiday Home in Hawkins

Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails.
9.8 out of 10, Exceptional, (20 reviews)
"Great place, location and hosts. "
United States
Paul H.
The price is HK$978
HK$1,197 total
includes taxes & fees
2 Mar - 3 Mar
Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails.
Property grounds

Camping in Butternut

Rustic campground in Butternut
The price is HK$352
HK$537 total
includes taxes & fees
2 Mar - 3 Mar
Rustic campground in Butternut
Property grounds

Cottage in Phillips

Lakefront cottage w/ convenient access to restaurants, atv and snowmobile trails
9.6 out of 10, Exceptional, (27 reviews)
"Very nice place enjoyed family time"
United States
Cheryl B.
The price is HK$901
HK$1,158 total
includes taxes & fees
2 Mar - 3 Mar
Lakefront cottage w/ convenient access to restaurants, atv and snowmobile trails
Exterior

Cabin in Butternut

Blissful cozy, year round, lakeside cabin on Butternut Lake. Dogs welcome.
10.0 out of 10, Exceptional, (77 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 HK$915
HK$2,484 total
includes taxes & fees
2 Mar - 3 Mar
Blissful cozy, year round, lakeside cabin on Butternut Lake. Dogs welcome.
Exterior

Condo in Phillips

Red Pines - Elk Lake Efficiency #6A
9.6 out of 10, Exceptional, (11 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 HK$1,192
HK$1,965 total
includes taxes & fees
2 Mar - 3 Mar
Red Pines - Elk Lake Efficiency #6A
Interior

Cabin in Exeland

Lunar Lodge on Windfall Lake
The price is HK$1,032
HK$3,732 total
includes taxes & fees
2 Mar - 3 Mar
Lunar Lodge on Windfall Lake
Terrace/patio

Condo in Cable

Telemark Northwoods Lodging
3.5 star property
9.0 out of 10, Wonderful, (316 reviews)
"Perfect lodging option in a wonderful location."
United States
Jason
The price is HK$1,338
HK$2,638 total
includes taxes & fees
2 Mar - 3 Mar
Telemark Northwoods Lodging
Smart TV

Holiday Home in Butternut

Cozy home in Wisconsin's recreational northwoods.
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 HK$704
HK$1,634 total
includes taxes & fees
2 Mar - 3 Mar
Cozy home in Wisconsin's recreational northwoods.
TV, fireplace

Holiday Home in Hayward

Lakefront Cabin on LCO - The Sunset Escape
9.6 out of 10, Exceptional, (5 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 HK$1,322
HK$3,918 total
includes taxes & fees
4 Mar - 5 Mar
Lakefront Cabin on LCO - The Sunset Escape
WiFi, bed sheets

Apartment in Hunter

Chip-Wa Lodging Room 6
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 HK$899
HK$1,273 total
includes taxes & fees
2 Mar - 3 Mar
Chip-Wa Lodging Room 6
Property grounds

Cabin in Hayward

Time to Hideout in Hayward!
The price is HK$1,211
HK$3,228 total
includes taxes & fees
2 Mar - 3 Mar
Time to Hideout in Hayward!
Property grounds

Holiday Home in Hayward

Motorsports Basecamp near lakes and forest
9.8 out of 10, Exceptional, (31 reviews)
"Wonderful accommodations. Great spot for a quick getaway!"
United States
Joe B.
The price is HK$981
HK$2,111 total
includes taxes & fees
2 Mar - 3 Mar
Motorsports Basecamp near lakes and forest
Interior

Cabin in Hayward

Northwoods Cabin Near Hayward Close to Snowmobile Trails and Nelson Lake
The price is HK$1,087
HK$4,442 total
includes taxes & fees
23 Mar - 24 Mar
Northwoods Cabin Near Hayward Close to Snowmobile Trails and Nelson Lake
Terrace/patio

Cabin in Ojibwa

Secluded Cabin w/Fresh Snow-Hot Tub, WIFI, King
10.0 out of 10, Exceptional, (47 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.
The price is HK$3,714
HK$4,455 total
includes taxes & fees
2 Mar - 3 Mar
Secluded Cabin w/Fresh Snow-Hot Tub, WIFI, King
Interior

Cabin in Hayward

2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
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 HK$782
HK$1,071 total
includes taxes & fees
2 Mar - 3 Mar
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
1 bedroom, WiFi, bed sheets

Cottage in Ladysmith

Ladysmith Cozy Cottage - Copper Tub - Waterfront
10.0 out of 10, Exceptional, (2 reviews)
"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 HK$1,077
HK$1,951 total
includes taxes & fees
10 Mar - 11 Mar
Ladysmith Cozy Cottage - Copper Tub - Waterfront
Outdoor dining

Cabin in Hayward

Lake Front Cabin, Media/Game Room, Connects to Trails--NEWLY REMODELED
10.0 out of 10, Exceptional, (9 reviews)
"Excellent property, exceptional hosts. "
United States
Michael H.
The price is HK$1,052
HK$2,728 total
includes taxes & fees
9 Mar - 10 Mar
Lake Front Cabin, Media/Game Room, Connects to Trails--NEWLY REMODELED
Interior

Apartment in Ladysmith

The Bunkhouse, cozy studio in adorable Ladysmith. Escape to the Northwoods!
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 HK$939
HK$1,156 total
includes taxes & fees
4 Mar - 5 Mar
The Bunkhouse, cozy studio in adorable Ladysmith. Escape to the Northwoods!
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

Cozy Cabin on Secluded Peninsula

Cozy Cabin on Secluded Peninsula

10/10 Excellent
"Clean, host was communicative and loved having toys at the cabin! "
Alexandra C. 2-night trip
Posted 2 days ago
Cozy Cabin on Secluded Peninsula

Find out more about Winter

Search for holiday rentals in Winter on Expedia! You can easily find your home rentals, villas, holiday apartments in Winter using one of the methods below:

  • View our selection of featured holiday rentals in Winter
  • Use the map to find apartments and other holiday homes in the Winter neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winter while they last

Look no further and take a look at our great range of rental properties in Winter!

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?

Lake Chippewa Flowage - Open Year Round, private home & dock, A/C, washer, dryer: This holiday home rental outside of Winter is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most of garden in this rental home to help you unwind.

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. 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.