Winter Holiday Rentals

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Holiday Rentals in Winter

Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

9.0 out of 10, Wonderful, (22)
"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.

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

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

Telemark Northwoods Lodging

3.5 star property
9.0 out of 10, Wonderful, (288)
"Perfect lodging option in a wonderful location."
The price is AU$230
includes taxes & fees
27 July - 28 July
Telemark Northwoods Lodging

Round Lake Cabin Retreat

9.4 out of 10, Exceptional, (66)
"Loves the location and beautiful Round Lake! Our family could all be together and relax with plenty of space!"
Round Lake Cabin Retreat

Victory Heights Haven – Sandy Shoreline on LCO

Victory Heights Haven – Sandy Shoreline on LCO

Phillips Cabin w/ Lake Views & Private Dock!

9.8 out of 10, Exceptional, (24)
"Beautiful, comfortable stay."
Phillips Cabin w/ Lake Views & Private Dock!

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

10.0 out of 10, Exceptional, (59)
"Loved our stay for Birkie weekend!"
The price is AU$920
includes taxes & fees
20 Aug - 21 Aug
Hayward, Round Lake Retreat! Private dock, 3 kayaks, beautifully maintained!

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!

9.8 out of 10, Exceptional, (195)
"Everything was very comfortable. It is BYOW(bring your own whisk) but thats it. Movie selection was great too"
The price is AU$478
includes taxes & fees
20 Aug - 21 Aug
Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!

Breezy Bay Beach On Round Lake

10.0 out of 10, Exceptional, (56)
"Beautiful place to stay."
Breezy Bay Beach On Round Lake

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

9.8 out of 10, Exceptional, (58)
"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

Modern Cabin located between Grindstone and Lac Courte Oreilles

10.0 out of 10, Exceptional, (65)
"This property was PERFECTION. Highly recommend and so grateful! "
Modern Cabin located between Grindstone and Lac Courte Oreilles

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

10.0 out of 10, Exceptional, (178)
"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

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!

Northwoods multiple family size cabin. ATV/UTV, snowmobile trail access and lake

9.6 out of 10, Exceptional, (28)
"Our large group stayed at the cabin while in town for a Men’s Hockey Tournament. The cabin was perfect for our group, good location for Stone Lake and Hayward, and easy access. There was plenty of space and the coordination of the cabin by Cassidy was great. Location was quiet, yet accessible. Would highly recommend, it was perfect for our group."
Northwoods multiple family size cabin. ATV/UTV, snowmobile trail access and lake

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

10.0 out of 10, Exceptional, (78)
"A wonderful location for wildlife and family fun!"
The fishing is great! Trails are close by. Enjoy summer in the Northwoods!

A Little Piece of Scandinavia In The North Woods, Spider Lake Chain, Hayward, WI

10.0 out of 10, Exceptional, (73)
"We had a great experience with this rental and the owners. The property had everything you need for your stay-all I’m great condition."
A Little Piece of Scandinavia In The North Woods, Spider Lake Chain, Hayward, WI

A-frame Cabin w/ Private Boat Dock!

3.0 star property
A-frame Cabin w/ Private Boat Dock!

" The Cabernet Cabin"

10.0 out of 10, Exceptional, (57)
"Beautiful place to take a family"
" The Cabernet Cabin"
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

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?

Bears Den on the private lake: This highly rated holiday home rental in Winter is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

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 Black Dan Lake are a couple of lovely local spots to get outside and enjoy nature. Chequamegon National Forest and Flambeau River 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.