Winter Holiday Rentals

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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov
In four months
12 Dec - 14 Dec

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, (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
EAGLE LODGE - Cozy Cabin Overlooking the Beautiful E. Fork of the Chippewa River
Smart TV

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

10.0 out of 10, Exceptional, (15)
"Beautiful views, beautiful cabins. Great resort bar that is always full of fun people. "
EAGLE LODGE - Cozy Cabin Overlooking the Beautiful E. Fork of the Chippewa River
Bucktail Lodge Lakeview Cabin on Barker Lake in Winter, Wisconsin
Exterior

Bucktail Lodge Lakeview Cabin on Barker Lake in Winter, Wisconsin

8.8 out of 10, Excellent, (5)
"Loved our stay at Bucktail Lodge! So beautiful. "
Bucktail Lodge Lakeview 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.

10.0 out of 10, Exceptional, (2)
"This quaint cozy cabin was just perfect. It had a vintage charm that brought back nostalgic memories.We spent mornings on the porch drinking coffee enjoying the view. We took advantage of hiking trails and places to explore in the area. Our host was very responsive when called. We would return again."
Vintage log cabin located in the Chequamegon National Forest on Blaisdell Lake.
Telemark Northwoods Lodging
Terrace/patio

Telemark Northwoods Lodging

3.5 star property
9.0 out of 10, Wonderful, (295)
"Perfect lodging option in a wonderful location."
The price is HK$1,151
HK$1,261 total
includes taxes & fees
25 Aug - 26 Aug
Telemark Northwoods Lodging
Round Lake Cabin Retreat
TV, fireplace, DVD player, books

Round Lake Cabin Retreat

9.4 out of 10, Exceptional, (69)
"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, (65)
"Loved our stay for Birkie weekend!"
Hayward, Round Lake Retreat! Private dock, 3 kayaks, beautifully maintained!
500' Lakeshore, 2 Docks, Sand Beach, Sleeps 10, A/C, Pontoon Boat for Rent
Exterior

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

9.8 out of 10, Exceptional, (59)
"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
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!

9.6 out of 10, Exceptional, (198)
"It would be difficult to find a cottage with a better lake view than this one. It's our second time here and we love it. Very comfortable in every respect."
Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!
Victory Heights Haven – Sandy Shoreline on LCO
Fridge, microwave, oven, stovetop

Victory Heights Haven – Sandy Shoreline on LCO

Victory Heights Haven – Sandy Shoreline on LCO
The Getaway on Grindstone Lake
Exterior

The Getaway on Grindstone Lake

10.0 out of 10, Exceptional, (12)
"Great location in the heart of lake country. Cabin is a on the shore of Grindstone lake facing west for excellent views of the sunset."
The Getaway on Grindstone Lake
A Little Piece of Scandinavia In The North Woods, Spider Lake Chain, Hayward, WI
Property grounds

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

10.0 out of 10, Exceptional, (76)
"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
Breezy Bay Beach On Round Lake
Smart TV, fireplace, DVD player, video library

Breezy Bay Beach On Round Lake

10.0 out of 10, Exceptional, (58)
"Beautiful place to stay."
Breezy Bay Beach On Round Lake
Round Lake Hideaway
Smart TV, fireplace, DVD player, video library

Round Lake Hideaway

9.0 out of 10, Wonderful, (29)
"Location was great; the kayaks and paddle boards were very nice. The living room furniture could use an upgrade .Overall it was a wonderful family trip!"
Round Lake Hideaway
Moose Lake Hayward WI
Terrace/patio

Moose Lake Hayward WI

2.0 star property
10.0 out of 10, Exceptional, (6)
"Our first time staying here. Perfect cabin for our weekend of fishing. Wish we had booked a couple more days. Walleye fishing was excellent. We will be back."
Moose Lake Hayward WI
Modern Cabin located between Grindstone and Lac Courte Oreilles
Outdoor dining

Modern Cabin located between Grindstone and Lac Courte Oreilles

10.0 out of 10, Exceptional, (69)
"This property was PERFECTION. Highly recommend and so grateful! "
Modern Cabin located between Grindstone and Lac Courte Oreilles
Exclusive Home On Chippewa Flowage- 3.6 acres with sand beach and two Private docks
6 bedrooms, iron/ironing board, WiFi, bed sheets

Exclusive Home On Chippewa Flowage- 3.6 acres with sand beach and two Private docks

9.6 out of 10, Exceptional, (8)
"Wonderful home and location."
Exclusive Home On Chippewa Flowage- 3.6 acres with sand beach and two Private docks
Executive Custom Log Lodge on Little Round Lake
Bar (on property)

Executive Custom Log Lodge on Little Round Lake

10.0 out of 10, Exceptional, (99)
"Comfortable, beautiful property!"
Executive Custom Log Lodge on Little Round Lake
Lakefront Wisconsin Cabin with Boat Dock!
TV, fireplace, DVD player

Lakefront Wisconsin Cabin with Boat Dock!

9.8 out of 10, Exceptional, (73)
"This was a great property. We are hoping to retire when the weather warms. "
Lakefront Wisconsin Cabin with Boat Dock!
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, (83)
"My partner and I stayed there for 3 nights in the middle of April. The cabin was very cozy, and the location was in the middle of a little bit of everything. Our favorite things were the screened in porch and the convince of the canoe. "
The fishing is great! Trails are close by. Enjoy summer in the Northwoods!
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
"We loved our annual stay in Hayward and the Northwoods."
Chuck 4-night trip
Posted 22 hours ago
Holiday Inn Express & Suites Hayward by IHG

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?

500' Lakeshore, 2 Docks, Sand Beach, Sleeps 10, A/C, Pontoon Boat for Rent: This holiday home rental outside of 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 4 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 Chequamegon National Forest are a couple of lovely local spots to get outside and enjoy nature. Flambeau River and Ojibwa State Park 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.