Winter Holiday Rentals

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Check prices for these dates

In two weeks
23 Jan - 25 Jan
In two months
6 Mar - 8 Mar
In three months
3 Apr - 5 Apr
In four months
1 May - 3 May

Our top choices for Winter holiday rentals

Terrace/patio
Telemark Northwoods Lodging

Condo in Cable

Telemark Northwoods Lodging
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 HK$1,331
HK$2,626 total
includes taxes & fees
11 Jan - 12 Jan
Telemark Northwoods Lodging
Property grounds
Rustic campground in Butternut

Camping in Butternut

Rustic campground in Butternut
1.0 star property
The price is HK$350
HK$534 total
includes taxes & fees
14 Jan - 15 Jan
Rustic campground in Butternut
Fridge, microwave, oven, stovetop
Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails.

Holiday Home in Hawkins

Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails.
2.0 star property
9.8 out of 10, Exceptional, (20)
"Amazing place to stay! So convenient and affordable, always a pleasure to stay😊"
United States
Hannah
The price is HK$973
HK$1,191 total
includes taxes & fees
12 Jan - 13 Jan
Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails.
Interior
Charming 2-bedroom house located in Ojibwa WI just off the Tuscobia Trail.

Holiday Home in Ojibwa

Charming 2-bedroom house located in Ojibwa WI just off the Tuscobia Trail.
2.0 star property
10.0 out of 10, Exceptional, (13)
"Very cozy, perfect for a family. Had everything we needed. "
United States
Erica C.
The price is HK$876
HK$1,532 total
includes taxes & fees
11 Jan - 12 Jan
Charming 2-bedroom house located in Ojibwa WI just off the Tuscobia Trail.
Exterior
Red Pines - Elk Lake #6A | Studio, 1 Bath

Holiday Home in Phillips

Red Pines - Elk Lake #6A | Studio, 1 Bath
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 HK$885
HK$1,183 total
includes taxes & fees
10 Jan - 11 Jan
Red Pines - Elk Lake #6A | Studio, 1 Bath
Interior
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage

Cabin in Hayward

2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
9.4 out of 10, Exceptional, (22)
"Cabin was clean. Everything 2 guys needed for a few days fishing."
United States
Tom N.
The price is HK$779
HK$1,067 total
includes taxes & fees
1 Feb - 2 Feb
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
Smart TV
Cozy home in Wisconsin's recreational northwoods.

Holiday Home in Butternut

Cozy home in Wisconsin's recreational northwoods.
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.
Cozy home in Wisconsin's recreational northwoods.
TV, books
Rock Garden Wisconsin Concrete Park | 3 Beds, comfortable and clean

Apartment in Phillips

Rock Garden Wisconsin Concrete Park | 3 Beds, comfortable and clean
2.0 star property
9.6 out of 10, Exceptional, (5)
"Super clean, friendly and great communication with property owner! "
United States
Kelly P.
The price is HK$1,400
HK$1,783 total
includes taxes & fees
10 Jan - 11 Jan
Rock Garden Wisconsin Concrete Park | 3 Beds, comfortable and clean
Property grounds
Lakefront cottage w/ convenient access to restaurants, atv and snowmobile trails

Cottage in Phillips

Lakefront cottage w/ convenient access to restaurants, atv and snowmobile trails
9.6 out of 10, Exceptional, (24)
"Very nice place enjoyed family time"
United States
Cheryl B.
The price is HK$1,401
HK$1,756 total
includes taxes & fees
11 Jan - 12 Jan
Lakefront cottage w/ convenient access to restaurants, atv and snowmobile trails
Property grounds
Red Pines - Elk Lake Condo #4 | 2 Bed, 1 Bath

Condo in Phillips

Red Pines - Elk Lake Condo #4 | 2 Bed, 1 Bath
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 HK$1,252
HK$1,620 total
includes taxes & fees
10 Jan - 11 Jan
Red Pines - Elk Lake Condo #4 | 2 Bed, 1 Bath
Interior
Red Pines - Elk Lake Condo #1 | 3 Bedroom, 1.5 Bath

Condo in Phillips

Red Pines - Elk Lake Condo #1 | 3 Bedroom, 1.5 Bath
10.0 out of 10, Exceptional, (13)
"Fantastic Place !!!!!! It was great and exactly what we needed!"
United States
Ryan
The price is HK$1,252
HK$1,620 total
includes taxes & fees
10 Jan - 11 Jan
Red Pines - Elk Lake Condo #1 | 3 Bedroom, 1.5 Bath
Property grounds
Modern Cabin with Classic Northwoods Experience...Close to Trails

Cabin in Hayward

Modern Cabin with Classic Northwoods Experience...Close to Trails
10.0 out of 10, Exceptional, (35)
"Absolutely stunning views, abundant wildlife, and peaceful. Would definitely recommend to anyone trying to escape! "
United States
Lily T.
Modern Cabin with Classic Northwoods Experience...Close to Trails
Property grounds
AVAIL BIRKIE|15min to trailhead, King Bed, PacMan

Cottage in Hayward

AVAIL BIRKIE|15min to trailhead, King Bed, PacMan
9.6 out of 10, Exceptional, (11)
"Wonderful place to stay.! Beautifully lake to kayak on."
United States
Katy R.
The price is HK$1,519
HK$3,531 total
includes taxes & fees
20 Jan - 21 Jan
AVAIL BIRKIE|15min to trailhead, King Bed, PacMan
Interior
The Bunkhouse, cozy studio in adorable Ladysmith. Escape to the Northwoods!

Apartment in Ladysmith

The Bunkhouse, cozy studio in adorable Ladysmith. Escape to the Northwoods!
2.0 star property
The price is HK$950
HK$1,166 total
includes taxes & fees
12 Jan - 13 Jan
The Bunkhouse, cozy studio in adorable Ladysmith. Escape to the Northwoods!
TV, fireplace
Lakefront Cabin on LCO - The Sunset Escape

Cabin in Hayward

Lakefront Cabin on LCO - The Sunset Escape
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 HK$1,505
HK$4,074 total
includes taxes & fees
14 Jan - 15 Jan
Lakefront Cabin on LCO - The Sunset Escape
Exterior
Blissful cozy, year round, lakeside cabin on Butternut Lake. Dogs welcome.

Cabin in Butternut

Blissful cozy, year round, lakeside cabin on Butternut Lake. Dogs welcome.
10.0 out of 10, Exceptional, (75)
"Amazing property right on the lake.100% worth staying there"
United States
Adam M.
The price is HK$1,016
HK$2,600 total
includes taxes & fees
10 Jan - 11 Jan
Blissful cozy, year round, lakeside cabin on Butternut Lake. Dogs welcome.
WiFi, bed sheets
Chip-Wa Lodging Room 1

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 HK$895
HK$1,267 total
includes taxes & fees
11 Jan - 12 Jan
Chip-Wa Lodging Room 1
Interior
Charming Northwoods Cabin Minutes from Hayward

Cabin in Hayward

Charming Northwoods Cabin Minutes from Hayward
2.0 star property
The price is HK$1,752
HK$4,715 total
includes taxes & fees
11 Jan - 12 Jan
Charming Northwoods Cabin Minutes from Hayward
Property grounds
Wiggle Weigel Lodges

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 HK$1,752
HK$2,955 total
includes taxes & fees
10 Jan - 11 Jan
Wiggle Weigel Lodges
Interior
Lunar Lodge on Windfall Lake

Cabin in Exeland

Lunar Lodge on Windfall Lake
The price is HK$1,205
HK$3,837 total
includes taxes & fees
10 Jan - 11 Jan
Lunar Lodge on Windfall Lake
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

Holiday Inn Express & Suites Hayward by IHG

Holiday Inn Express & Suites Hayward by IHG

10/10 Excellent
"Clean, accommodating and very nice"
Terri 2-night trip
Posted 5 days ago
Holiday Inn Express & Suites Hayward by IHG

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?

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 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 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.