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Winter Holiday Rentals

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Winter holiday rentals

A tray with breakfast items including eggs, bacon, and a muffin, a glass of orange juice, and a hot tub in the background.

1. Secluded Riverfront Cabin | Hot Tub + Starlink

Secluded Riverfront Cabin | Hot Tub + Starlink
Ojibwa
10.0 out of 10, Exceptional, (49 reviews)
"We had such a good time! "
United States
Dan P.
The price is HK$3,562
HK$4,239 total
includes taxes & fees
8 Nov - 9 Nov
Secluded Riverfront Cabin | Hot Tub + Starlink
A wooden deck with two wicker chairs and a table, overlooking a forest with autumn foliage.

2. Telemark Northwoods Lodging

Telemark Northwoods Lodging
3.5 star property
Cable
9.0 out of 10, Wonderful, (331 reviews)
"Clean, quiet…easy check in. Great communication pre check-in. Beautiful setting/area. Will be back…"
United States
Thomas
The price is HK$734
HK$1,981 total
includes taxes & fees
3 Nov - 4 Nov
Telemark Northwoods Lodging
A view through a window of a grassy yard with a pond, trees, and a small building.

3. 2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage

2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
Hayward
8.4 out of 10, Very good, (11 reviews)
"Cabin was perfect for our needs. Host met us and let us know the important information about the property and let us be. Would stay again."
United States
Katie L.
The price is HK$784
HK$1,005 total
includes taxes & fees
1 Nov - 2 Nov
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
A cozy room with a bed, a sofa, a wooden wall, a door, and a small table with a lamp.

4. Chip-Wa Lodging Room 1

Chip-Wa Lodging Room 1
Hunter
10.0 out of 10, Exceptional, (3 reviews)
"Enjoyed our stay. Cozy and quaint."
United States
Thane B.
The price is HK$902
HK$1,208 total
includes taxes & fees
2 Nov - 3 Nov
Chip-Wa Lodging Room 1
A view through a window of a grassy yard with a lake, trees, and a small building.

5. 2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage

2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
Hayward
9.2 out of 10, Wonderful, (26 reviews)
"We liked the property and the cabin was fine. Management was not available and there was no communication. The grounds were in need of up keep. The weather was tremendous. All in all we had a good stay because we are simple folks that know how to enjoy ourselves."
United States
Dawn
The price is HK$784
HK$1,005 total
includes taxes & fees
2 Nov - 3 Nov
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
A campsite with a trailer, a tent, and a car.

6. Rustic campground in Butternut

Rustic campground in Butternut
Butternut
The price is HK$353
HK$538 total
includes taxes & fees
1 Nov - 2 Nov
Rustic campground in Butternut
An outdoor seating area with Adirondack chairs and a fire pit, surrounded by a forested landscape.

7. Kavanagh Bay Resort|Hot Tub&Sauna #1

Kavanagh Bay Resort|Hot Tub&Sauna #1
Hayward
7.2 out of 10, Good, (5 reviews)
"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.
The price is HK$1,304
HK$4,321 total
includes taxes & fees
1 Nov - 2 Nov
Kavanagh Bay Resort|Hot Tub&Sauna #1
A rustic log cabin with a green roof, a small porch, and a view of a lake.

8. 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, (79 reviews)
"Cute and cozy winter rental. Looks like it would be a great summer spot too!"
United States
David M.
The price is HK$1,024
HK$2,653 total
includes taxes & fees
1 Nov - 2 Nov
Blissful cozy, year round, lakeside cabin on Butternut Lake. Dogs welcome.
A wooden cabin with a porch, surrounded by trees with autumn foliage.

9. Lake Cabin · Hot Tub · Fire Pit · Free Firewood

Lake Cabin · Hot Tub · Fire Pit · Free Firewood
Hayward
9.8 out of 10, Exceptional, (25 reviews)
"the place is in good shape and the location is awesome. "
United States
Kevin R.
The price is HK$2,391
HK$5,898 total
includes taxes & fees
3 Nov - 4 Nov
Lake Cabin · Hot Tub · Fire Pit · Free Firewood
Private kitchen

10. 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
10.0 out of 10, Exceptional, (30 reviews)
"Great place, location and hosts. "
United States
Paul H.
The price is HK$981
HK$1,134 total
includes taxes & fees
1 Nov - 2 Nov
Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails.
A spacious living area with a wooden floor, a sofa, a coffee table, and a kitchen area with a large window.

11. Renovated cabin on Lac Courte Oreilles Lake - minutes from trails!

Renovated cabin on Lac Courte Oreilles Lake - minutes from trails!
Northwoods Beach
10.0 out of 10, Exceptional, (26 reviews)
"Our second time staying and we love it! We especially enjoyed the addition of the front/lake facing deck "
United States
ANN M.
The price is HK$1,483
HK$2,615 total
includes taxes & fees
3 Nov - 4 Nov
Renovated cabin on Lac Courte Oreilles Lake - minutes from trails!
A wooden staircase leading to a deck with a house in the background.

12. Motorsports Basecamp near lakes and forest

Motorsports Basecamp near lakes and forest
Hayward
9.8 out of 10, Exceptional, (34 reviews)
"Excellent host and accommodations."
United States
Ben S.
The price is HK$918
HK$2,216 total
includes taxes & fees
1 Nov - 2 Nov
Motorsports Basecamp near lakes and forest
A living room with a wooden floor, a television mounted on the wall, a desk with a chair, a sofa, and a lamp.

13. Cozy home in Wisconsin's recreational northwoods.

Cozy home in Wisconsin's recreational northwoods.
Butternut
7.6 out of 10, Good, (5 reviews)
"Weather was hot, fishing was difficult at best, we had a good time."
United States
Robert
The price is HK$941
HK$1,738 total
includes taxes & fees
1 Nov - 2 Nov
Cozy home in Wisconsin's recreational northwoods.
A log cabin with a fire pit and chairs in a wooded area.

14. Red Pines - Elk Lake Efficiency #6A

Red Pines - Elk Lake Efficiency #6A
Phillips
9.6 out of 10, Exceptional, (16 reviews)
"Nice room but the futon bed was tilting and not comfortable. Otherwise a good room and good value. Better for 2 people than 3."
United States
Reuben
The price is HK$1,200
HK$1,881 total
includes taxes & fees
1 Nov - 2 Nov
Red Pines - Elk Lake Efficiency #6A
Interior

15. Ultimate Hayward Trailhead Cabin

Ultimate Hayward Trailhead Cabin
Hayward
10.0 out of 10, Exceptional, (1 review)
"My husband and I had a wonderful stay at this cabin. The pictures and description are totally accurate. The home was clean, well furnished and as comfortable as home including the beds. The kitchen was well equipped with everything we needed and the linnens were fresh, new and plush. The shower is spacious and there was plenty of hot water. The screened porch was wonderful to sit out in the afternoon and watch the leaves fall in the breeze. (We were there early October). We found lots of...
United States
Joan O.
The price is HK$1,174
HK$2,259 total
includes taxes & fees
5 Nov - 6 Nov
Ultimate Hayward Trailhead Cabin
A wooden sauna with a sliding glass door, two white lanterns, and the text "sunlighters Amplify" on the glass.

16. Flambeau River Gem | Tiny Home w/Sauna

Flambeau River Gem | Tiny Home w/Sauna
Park Falls
9.8 out of 10, Exceptional, (12 reviews)
"Tina was a great communicator and the property was perfect for us. Highly recommend."
United States
Peggy C.
The price is HK$1,338
HK$3,494 total
includes taxes & fees
2 Nov - 3 Nov
Flambeau River Gem | Tiny Home w/Sauna
A rustic cabin surrounded by dense forest.

17. 2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage

2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
Hayward
8.4 out of 10, Very good, (20 reviews)
"Thank you for the great stay! I had everything I needed."
United States
Mark B.
The price is HK$981
HK$1,231 total
includes taxes & fees
18 Nov - 19 Nov
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
A gravel driveway leading to a small, single-story building surrounded by dense trees and greenery.

18. Comfortable 3 Bedroom Cabin On the Shores of Lake Chippewa Flowage in Hayward WI

Comfortable 3 Bedroom Cabin On the Shores of Lake Chippewa Flowage in Hayward WI
Hayward
9.2 out of 10, Wonderful, (10 reviews)
"We felt like we we transported to the 60’s. The atmosphere and ambiance fit. We had everything we needed and the management was great. If you want old school WI resort this is your place!"
United States
Nina H.
The price is HK$1,569
HK$1,959 total
includes taxes & fees
22 Nov - 23 Nov
Comfortable 3 Bedroom Cabin On the Shores of Lake Chippewa Flowage in Hayward WI
A wooden staircase with a handrail, a door leading to an outdoor area with a rocking chair, and a wooden floor inside.

19. Hayward Basecamp Near Nelson Lake, Phipps Flowage & Downtown

Hayward Basecamp Near Nelson Lake, Phipps Flowage & Downtown
Hayward
The price is HK$1,501
HK$3,783 total
includes taxes & fees
2 Nov - 3 Nov
Hayward Basecamp Near Nelson Lake, Phipps Flowage & Downtown
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
"From check in to check out the place was clean, beautiful room and delicious breakfast especially loved the cinnamon rolls and the fresh coffee"
Cynthia 1-night trip
Posted 16 hours 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?

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 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. Lake Chippewa 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.