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Winter Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Winter vacation 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 ￥71,041
￥85,754 total
includes taxes & fees
Nov 12 - Nov 13
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 ￥14,180
￥15,527 total
includes taxes & fees
Nov 3 - Nov 4
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 ￥15,756
￥20,187 total
includes taxes & fees
Nov 3 - Nov 4
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 ￥18,112
￥24,266 total
includes taxes & fees
Nov 3 - Nov 4
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 ￥15,756
￥20,187 total
includes taxes & fees
Nov 5 - Nov 6
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 ￥7,090
￥9,475 total
includes taxes & fees
Nov 3 - Nov 4
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 ￥26,199
￥86,795 total
includes taxes & fees
Nov 3 - Nov 4
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 ￥20,562
￥50,617 total
includes taxes & fees
Nov 3 - Nov 4
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 ￥48,013
￥118,455 total
includes taxes & fees
Nov 8 - Nov 9
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 ￥19,695
￥22,774 total
includes taxes & fees
Nov 10 - Nov 11
Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails.
A spacious living area with a sofa, dining table, and kitchen.

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 ￥29,779
￥52,529 total
includes taxes & fees
Nov 3 - Nov 4
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 ￥18,435
￥44,514 total
includes taxes & fees
Nov 3 - Nov 4
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 ￥18,907
￥34,909 total
includes taxes & fees
Nov 3 - Nov 4
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 ￥24,111
￥37,787 total
includes taxes & fees
Nov 5 - Nov 6
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 ￥23,576
￥45,368 total
includes taxes & fees
Nov 4 - Nov 5
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 ￥27,620
￥71,176 total
includes taxes & fees
Nov 8 - Nov 9
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 ￥19,695
￥24,715 total
includes taxes & fees
Nov 18 - Nov 19
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 ￥31,512
￥39,336 total
includes taxes & fees
Nov 18 - Nov 19
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 ￥30,149
￥75,975 total
includes taxes & fees
Nov 4 - Nov 5
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 3 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 vacation rental in Winter?

Yes, you can find vacation rentals near top attractions in Winter, or you can choose a more secluded option if you're looking for relaxation.

What's the top vacation rental in Winter?

5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.: Visitors give good reviews to this Winter vacation home rental, which is located on a lake and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games. Our travelers also rate Amazing Sunsets, Peaceful, Well Maintained Lake home on Beautiful, Barker lake as a favorite home for rent in Winter.

How many vacation rentals are there in Winter?

Choose from 11 Expedia vacation rentals in Winter for a memorable vacation.

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 vacation rentals like in Winter?

Vacation rentals are privately owned accommodations you can stay in for several days or longer in Winter. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll have a home away from home. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for a small group gathering.