Winter Holiday Rentals

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Holiday Rentals in Winter

Spacious Winter Retreat w/ River Access + Kayaks!

9.0 out of 10, Wonderful, (18)
"This has been the second year we’ve been here. It’s a great place for a large group with plenty of space for everyone! This will continue to be our go to spot for years to come! "
Spacious Winter Retreat w/ River Access + Kayaks!

Bears Den on the private lake

9.6 out of 10, Exceptional, (26)
"The lake was great and the living situation for our large group was very comfortable. The only reason I give it 4 stars is because there was no hot water. The showers were absolutely freezing. Besides that everything was great."
Bears Den on the private lake

Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

8.8 out of 10, Excellent, (17)
"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

Telemark Northwoods Lodging

3.5 star property
9.0 out of 10, Wonderful, (256)
"Very clean and very comfortable "
The price is NZ$240
includes taxes & fees
24 Dec - 25 Dec
Telemark Northwoods Lodging

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

9.6 out of 10, Exceptional, (183)
"Was one of the nice's places we've stayed at in the last 10 year's."
Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!

Beautiful Ponderosa Pine Log Cabin - Northwoods Retreat On 10 Acres

10.0 out of 10, Exceptional, (242)
"We had a wonderful weekend relaxing in the cabin. Lots of time spent laughing, soaking in the hot tub, and playing games or painting inside while it rained. We would definitely come back."
Beautiful Ponderosa Pine Log Cabin - Northwoods Retreat On 10 Acres

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

9.6 out of 10, Exceptional, (25)
"We had a lovely and cozy stay! The backyard was just amazing and peaceful...had everything we could want. Only downfall was the mattresses in the bunkroom....very uncomfortable and one of the beds broke. Otherwise, a super place!"
Northwoods multiple family size cabin. ATV/UTV, snowmobile trail access and lake

Round Lake Cabin Retreat

9.4 out of 10, Exceptional, (63)
"no tv,one in basement nothing to hook up to.On crappy days and nights would of been useful'."
Round Lake Cabin Retreat

Lake Hayward. Private Lakefront Within Walking Distance To Downtown Hayward

9.8 out of 10, Exceptional, (106)
"Overall it was a nice stay ,we were out exploring things so we were not at the house alot but when we were there it was comfortable. It had everything we needed for our stay there I wish the weather would’ve been warmer so we could experience the lake a little bit more, but it was still a nice stay"
Lake Hayward. Private Lakefront Within Walking Distance To Downtown Hayward

Backyard Trails and Lake Hayward with Canoe!

9.6 out of 10, Exceptional, (21)
"Absolutley loved our stay. Property was clean and very nice. The location was very convienent being close to town, but also seeming secluded at the same time. Property owner was very kind and had great communication. Very nice stay, enjoyed every minute of it."
Backyard Trails and Lake Hayward with Canoe!

Family Friendly Cottage w/Spectacular Views of Round Lake-Hayward, WI

10.0 out of 10, Exceptional, (113)
"This was our second time staying here and we will be back! Such an accommodating cabin. The views of the lake are beautiful, so serene and quiet.It’s immaculately, clean and stashed with anything we could possibly need. There are drawers with board games.The sunroom is a perfect spot to play games and read as a family. The basement ping pong table and dart board are an added bonus. Greta is a wonderful host and we can’t wait to be back!"
Family Friendly Cottage w/Spectacular Views of Round Lake-Hayward, WI

North Fork Flambeau River near Park Falls, 3BR, 1BA country home, on ATV route.

9.6 out of 10, Exceptional, (11)
"This was a nice location with a great view "
North Fork Flambeau River near Park Falls, 3BR, 1BA country home, on ATV route.

Avail. New Year's w/Hot Tub, WIFI, King Beds

10.0 out of 10, Exceptional, (39)
"We booked this for a little family week getaway, it checked all of our boxes. Close to water, secluded, cozy, the hot tub, and enough space for all of us! The hosts are amazing and very communicative before and during your stay if you have any questions or feedback! We brought a couple extra kayaks, and used the ones on the property. There is a launch just up the road that gives you about 30 minutes, and another just a bit further that was just over an hour. The fire pit near the water was...
The price is NZ$879
includes taxes & fees
5 Jan - 6 Jan 2025
Avail. New Year's w/Hot Tub, WIFI, King Beds

Charming Butternut Lake Getaway w/ Deck & Dock!

9.6 out of 10, Exceptional, (15)
"Peaceful, comfortable home. All the beds were very comfortable, thank you. Grouse hunting was disappointing in the area. Wisconsin is a beautiful state and we will return someday to hunt another part of the state."
Charming Butternut Lake Getaway w/ Deck & Dock!

Lakefront Wisconsin Cabin with Boat Dock!

9.6 out of 10, Exceptional, (67)
"Very quiet and comfortable place to stay. I would like to return with friends to fish. The availability of renting the pontoon was fantastic. The whole family enjoyed our stay "
Lakefront Wisconsin Cabin with Boat Dock!

Cozy Cabin on Secluded Peninsula

9.8 out of 10, Exceptional, (38)
"We had a perfect weekend staying at the cabin. Collin was really helpful. Checking in was a breeze and the cabin is well equipped with everything you could want. The cabin is located at the end of a pennisula, which makes it very private and the perfect place for some time in the North Woods!"
Cozy Cabin on Secluded Peninsula

Burns Lake Cabin w/ Dock, Fire Pit, Rowboat & More

8.8 out of 10, Excellent, (38)
"Cabin and location very nice "
Burns Lake Cabin w/ Dock, Fire Pit, Rowboat & More

Quiet Sports Oasis-Wooded & Private-Ski In/Ski Out

10.0 out of 10, Exceptional, (45)
"We had the coziest weekend here! The cabin was warm, just the right size, and very well stocked. We appreciated the easy access to ski trails and the simple check in/check out process. I’d love to stay here again!"
Quiet Sports Oasis-Wooded & Private-Ski In/Ski Out

Secluded Cabin on 13 acres; Private 50 acre lake

10.0 out of 10, Exceptional, (97)
"The home was perfect for us. We enjoyed 5 peaceful days with our two dogs. Esther was a pleasure to work with and the property has everything you need. Bonus is the location, and we were fortunate to experience the beautiful fall colors during our time. If you are looking for a relaxing place to escape your busy lives, this is it."
Secluded Cabin on 13 acres; Private 50 acre lake

Peaceful cabin on the Flambeau River

10.0 out of 10, Exceptional, (120)
"It was amazing, very clean, and exactly like what was pictured "
Peaceful cabin on the Flambeau River
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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Other types of properties in Winter you may be interested in

Spacious Winter Retreat w/ River Access + Kayaks!

9.0 out of 10, Wonderful, (18)
"This has been the second year we’ve been here. It’s a great place for a large group with plenty of space for everyone! This will continue to be our go to spot for years to come! "
Spacious Winter Retreat w/ River Access + Kayaks!

Bears Den on the private lake

9.6 out of 10, Exceptional, (26)
"The lake was great and the living situation for our large group was very comfortable. The only reason I give it 4 stars is because there was no hot water. The showers were absolutely freezing. Besides that everything was great."
Bears Den on the private lake

Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

8.8 out of 10, Excellent, (17)
"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
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.

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?

Spacious Winter Retreat w/ River Access + Kayaks!: This highly rated holiday home rental in Winter offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 7 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 Bears Den on the private lake as a favourite home for rent in Winter.

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. Winter Town Hall 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.