Winter Holiday Rentals

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Check prices for these dates

Tonight
8 Jul - 9 Jul
Tomorrow
9 Jul - 10 Jul
This weekend
11 Jul - 13 Jul
Next weekend
18 Jul - 20 Jul

Holiday Rentals in Winter

Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin
Exterior

Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

9.0 out of 10, Wonderful, (19)
"Owner made the check in process a breeze. Quaint and great spot in a nice location, definitely will be staying again. Thank you Bucktail Lodge! "
Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin
Vintage log cabin located in the Chequamegon National Forest on Blaisdell Lake.
Outdoor dining

Vintage log cabin located in the Chequamegon National Forest on Blaisdell Lake.

Vintage log cabin located in the Chequamegon National Forest on Blaisdell Lake.
Luxury Cabin, 800+ feet frontage, 733 acre Lake, Hot tub, Pontoon, Fireplace .
Fridge, microwave, oven, stovetop

Luxury Cabin, 800+ feet frontage, 733 acre Lake, Hot tub, Pontoon, Fireplace .

10.0 out of 10, Exceptional, (26)
"Couldn't have asked for a better romantic getaway!"
Luxury Cabin, 800+ feet frontage, 733 acre Lake, Hot tub, Pontoon, Fireplace .
EAGLE LODGE - Cozy Cabin Overlooking the Beautiful E. Fork of the Chippewa River
1 bedroom, free WiFi, bed sheets

EAGLE LODGE - Cozy Cabin Overlooking the Beautiful E. Fork of the Chippewa River

10.0 out of 10, Exceptional, (12)
"Great cabin! Loved being by freinds . Love this campground."
EAGLE LODGE - Cozy Cabin Overlooking the Beautiful E. Fork of the Chippewa River
Bears Den on the private lake
Interior

Bears Den on the private lake

9.6 out of 10, Exceptional, (26)
"Well outfitted cabin - had a group of 10 and had plenty of space, cooking-ware, and plates. Hosts were very responsive. Kids enjoyed splashing in the water and swimming back and forth from the swim platform. Would stay again."
Bears Den on the private lake
Telemark Northwoods Lodging
Terrace/patio

Telemark Northwoods Lodging

3.5 star property
9.0 out of 10, Wonderful, (279)
"Perfect lodging option in a wonderful location."
The price is HK$876
HK$959 total
includes taxes & fees
20 Jul - 21 Jul
Telemark Northwoods Lodging
Phillips Cabin w/ Lake Views & Private Dock!
Fridge, microwave, stovetop, dishwasher

Phillips Cabin w/ Lake Views & Private Dock!

9.8 out of 10, Exceptional, (23)
"Beautiful, comfortable stay."
Phillips Cabin w/ Lake Views & Private Dock!
Moose Lake Hayward WI
Terrace/patio

Moose Lake Hayward WI

2.0 star property
10.0 out of 10, Exceptional, (5)
"It was an amazing stay. The lake was beautiful even frozen. Quiet, cozy, comfortable. All around relaxing and Amazing stay. Will 100% stay again."
Moose Lake Hayward WI
Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!
Dining

Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!

9.8 out of 10, Exceptional, (192)
"Everything was very comfortable. It is BYOW(bring your own whisk) but thats it. Movie selection was great too"
Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!
Modern Cabin located between Grindstone and Lac Courte Oreilles
Exterior detail

Modern Cabin located between Grindstone and Lac Courte Oreilles

10.0 out of 10, Exceptional, (63)
"This property was PERFECTION. Highly recommend and so grateful! "
Modern Cabin located between Grindstone and Lac Courte Oreilles
Round Lake Cabin Retreat
TV, fireplace, DVD player, books

Round Lake Cabin Retreat

9.4 out of 10, Exceptional, (65)
"Loves the location and beautiful Round Lake! Our family could all be together and relax with plenty of space!"
Round Lake Cabin Retreat
Hayward, Round Lake Retreat! Private dock, 3 kayaks, beautifully maintained!
Property grounds

Hayward, Round Lake Retreat! Private dock, 3 kayaks, beautifully maintained!

10.0 out of 10, Exceptional, (57)
"Loved our stay for Birkie weekend!"
The price is HK$2,975
HK$5,690 total
includes taxes & fees
23 Jul - 24 Jul
Hayward, Round Lake Retreat! Private dock, 3 kayaks, beautifully maintained!
On a 3200 acre lake with 400 ft of frontage. Great fishing kayaking boating fun
Exterior

On a 3200 acre lake with 400 ft of frontage. Great fishing kayaking boating fun

10.0 out of 10, Exceptional, (175)
"We had a great time at this cabin. Hosts were amazing, property was clean and very enjoyable, will go back again. "
On a 3200 acre lake with 400 ft of frontage. Great fishing kayaking boating fun
" The Cabernet Cabin"
Exterior

" The Cabernet Cabin"

10.0 out of 10, Exceptional, (55)
"Beautiful place to take a family"
" The Cabernet Cabin"
The fishing is great! Trails are close by. Enjoy summer in the Northwoods!
Fireplace, books, stereo

The fishing is great! Trails are close by. Enjoy summer in the Northwoods!

10.0 out of 10, Exceptional, (75)
"A wonderful location for wildlife and family fun!"
The fishing is great! Trails are close by. Enjoy summer in the Northwoods!
500' Lakeshore, 2 Docks, Sand Beach, Sleeps 10, A/C, Pontoon Boat for Rent
Miscellaneous

500' Lakeshore, 2 Docks, Sand Beach, Sleeps 10, A/C, Pontoon Boat for Rent

9.8 out of 10, Exceptional, (57)
"Nice roomy property for 6 fishermen to enjoy a few days on the water."
500' Lakeshore, 2 Docks, Sand Beach, Sleeps 10, A/C, Pontoon Boat for Rent
Cabin with private dock and large yard space!
2 bedrooms, free WiFi, bed sheets

Cabin with private dock and large yard space!

9.6 out of 10, Exceptional, (47)
"This little place was a perfect get away for our family! Awesome lake to ice fish, and just a short walk from the bar!"
Cabin with private dock and large yard space!
Rustic and Charming one Bedroom cabin. Upgraded pontoon!
Smart TV, fireplace, DVD player

Rustic and Charming one Bedroom cabin. Upgraded pontoon!

9.6 out of 10, Exceptional, (91)
"This was our 3rd stay! We love it. "
Rustic and Charming one Bedroom cabin. Upgraded pontoon!
Wisconsin Lakeside Cottage w/ Deck, Views
Fridge, microwave, coffee/tea maker, toaster

Wisconsin Lakeside Cottage w/ Deck, Views

2.0 star property
7.2 out of 10, Good, (5)
"Loved it, every part of it!"
Wisconsin Lakeside Cottage w/ Deck, Views
Charming 5-bedroom cabin just outside Hayward near OO, Tiger Cat,and Spider Lake
Exterior

Charming 5-bedroom cabin just outside Hayward near OO, Tiger Cat,and Spider Lake

2.0 star property
10.0 out of 10, Exceptional, (4)
"Simple Checkin, Responsive Host, Nice Location and property equipped to host 20+ person. Stayed 2 memorable and fun nights...."
Charming 5-bedroom cabin just outside Hayward near OO, Tiger Cat,and Spider 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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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?

Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails: This holiday home rental outside Winter is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

How many holiday rentals are there in Winter?

Choose from 13 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.