Holiday Homes in Winter

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Featured Holiday Homes in Winter

Spacious Winter Retreat w/ River Access + Kayaks!

9.0 out of 10, Wonderful, (17)
"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!

Ackwood Lodge - The Lodge, LARGE, Private Lakeshore Estate. Perfect for Family Reunions

10.0 out of 10, Exceptional, (18)
"We stayed at Ackwood Lodge for a long weekend celebrating my sister’s bachelorette. The accommodations were perfect for a larger party. Adam was great with communication and responded quickly. I would stay here again in a heartbeat!!"
Ackwood Lodge - The Lodge, LARGE, Private Lakeshore Estate. Perfect for Family Reunions

Majestic views, classic charm, lifelong memories.

10.0 out of 10, Exceptional, (37)
"Sweet little spot nestled on the edge of the lake - loons, eagles, the lapping of water on the shore, blue sky and pine trees. Everything a couple of city-dwellers needs to decompress and unwind. Great location to explore the woods in the area - mountain biking trails and unique dining experiences nearby. Highly recommend a trip to Delta Diner, we loved it. Chris was a true pleasure to chat with, he couldn't have been more accommodating helping us get situated. Cabin is comfy and has a great...
Majestic views, classic charm, lifelong memories.

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

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.

Renovated Historic Church Along Namekagon River!

9.8 out of 10, Exceptional, (19)
"Such a cool place to stay! Great bike trails too. We had a great time."
Renovated Historic Church Along Namekagon River!

Mallard Manor

10.0 out of 10, Exceptional, (8)
"Great stay, excellent attention to detail. Outstanding space for a group with tons of parking + comfortable sleeping spots for all. "
Mallard Manor

6 bedroom 3- bath 16 people capacity pontoon included in Winter Wis.

10.0 out of 10, Exceptional, (52)
"We loved the property. The house is spacious and beautiful. The game room provided many hours of fun! We were a little surprised at the cleaning "rules" and that we had to make our own beds. That would be the only negative thing we had to say about this property."
6 bedroom 3- bath 16 people capacity pontoon included in Winter Wis.

Scooter's Landing in Hinton Bay on Round Lake, the view is amazing!

8.6 out of 10, Excellent, (14)
"2nd annual trip to Round Lake. 1st stay at Scooter's Landing. This cabin was perfect for our family get together. Our little pugs loved the decks and we loved the sauna and the awesome views of the bay. I recommend this property to others who enjoy lakeside life and if you have a boat it is so close to the landing. Great owner and we had no issues!"
Scooter's Landing in Hinton Bay on Round Lake, the view is amazing!

Secluded 4-season cabin w/private waterfront, epic game room & mins from trails

10.0 out of 10, Exceptional, (40)
"We saw this property and we both needing time away without distractions from stressful work environments enjoyed this beautiful cabin and fun game room that kept us young at heart. What was a relaxing weeks turned into an engagement and our memories started at this cabin… so thank you!!! Amazing hosts that thought of everything from more kits to all the needed for the best stay . "
Secluded 4-season cabin w/private waterfront, epic game room & mins from trails

Secluded Log Home in the NATIONAL FOREST. ATV TRAILS CROSS OUR PROPERTY

9.6 out of 10, Exceptional, (138)
"This will be 25 yrs + for our group of guys annual hunting and fishing trip staying in the area. This is our 2nd year here and all the guys commented that this is the best place so far. It is close to all our favorite hunting and fishing spots and is the most spacious place we have ever stayed with plenty of room for all our gear and to spread out. The huge yard and endless woods to explore at the back door is amazing as well as the beautiful Ghost Creek that leads you to the Chippewa. This...
Secluded Log Home in the NATIONAL FOREST. ATV TRAILS CROSS OUR PROPERTY

THE 1852 LOG HOUSE.

10.0 out of 10, Exceptional, (31)
"The hosts were wonderful and the cabin was excellently appointed to be able to properly cook great meals. Everything in the kitchen you could need is there for use. Be mindful that this cabin sits on regulaly travelled road, so expect some quick road traffic"
THE 1852 LOG HOUSE.

Beautiful round lake northern cedar modern vacation home

9.6 out of 10, Exceptional, (35)
"This was our second time staying at this beautiful lake home & we had such a wonderful stay both times! The layout of the home is perfect to give everyone space or be all together. The flat front yard gives a nice place to play yard games & allows for easy access to the dock for young and old! The property owner is very responsive & friendly.We’re excited to return next year! Kelly"
Beautiful round lake northern cedar modern vacation home

Special Pricing, 39% off For All New Bookings!

10.0 out of 10, Exceptional, (1)
"Beautiful cabin with something for everyone in the family! Great views, and easy to work with owners . Would definitely stay again! "
Special Pricing, 39% off For All New Bookings!

Sugar Maple at Hansen Lake, 6 Beds, Historic Charm

10.0 out of 10, Exceptional, (5)
"The property was well stocked with everything you would need for a family vacation, cozy family room with a beautiful wood burning fire place. The property was centered on Hansen Lake with beautiful views and a peaceful setting.My kids loved the playing games at night by the fireplace and playing outside during the day. Would recommend this property for any season "
Sugar Maple at Hansen Lake, 6 Beds, Historic Charm

Cozy 3 bedroom house in a small town, close to recreational and fishing areas.

2.0 star property
9.6 out of 10, Exceptional, (4)
"Very clean and quiet area. Will definitely come back!"
The price is AU$238
includes taxes & fees
24 Nov - 25 Nov
Cozy 3 bedroom house in a small town, close to recreational and fishing areas.

Charming 2-bedroom house located in Ojibwa WI just off the Tuscobia Trail.

2.0 star property
The price is AU$326
includes taxes & fees
25 Nov - 26 Nov
Charming 2-bedroom house located in Ojibwa WI just off the Tuscobia Trail.

The Elk Inn on Lower Clam Lake - Beautiful New Cabin!

2.0 star property
9.0 out of 10, Wonderful, (2)
"I want one!! Perfect size. Love the decor. This is what I dream of for a cabin!!! They thought of everything! Love the heated floors!! So cozy! The electric fireplace added to the ambiance! Location for our off road adventures was perfect! Truly can’t wait to stay again!! Did I mention I LOVED the cabin?! Great communication w the owners/property manager! Courteous, prompt, and respectful. Thank you for letting us stay! "
The Elk Inn on Lower Clam Lake - Beautiful New Cabin!

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

Located in the heart of bike & ATV trails, Fish, hike, kayak this summer.

10.0 out of 10, Exceptional, (69)
"All positives about this property. Fully loaded with amenities. Very clean. Nice kitchen. Loved the screened porch. Quiet location. Comfortable furnishings. Lovely spring with swans. Great location near numerous hiking & biking trailheads."
Located in the heart of bike & ATV trails, Fish, hike, kayak this summer.
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 property types in Winter

Spacious Winter Retreat w/ River Access + Kayaks!

9.0 out of 10, Wonderful, (17)
"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!

Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

8.8 out of 10, Excellent, (16)
"Newer owner is showing improvement to property."
Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

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
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.