Holiday Homes in Winter

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Featured Holiday Homes in Winter

Spacious Winter Retreat w/ River Access + Kayaks!
TV, fireplace, DVD player, table football

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!
Sandalwood Retreat on Round Lake - Enjoy our screened porch & gorgeous sunsets 
Interior

Sandalwood Retreat on Round Lake - Enjoy our screened porch & gorgeous sunsets 

10.0 out of 10, Exceptional, (36)
"We are a group of 11 adults that go on an annual Labor Day trip every year, and this was the best year yet thanks to the Sandalwood Retreat. The house had more than enough space for everyone and their belongings. We were thankful to have two full kitchens and multiple places indoors and outdoors to hang out. Whether we were hanging out as a large group or we were split up into smaller groups or enjoying some alone time, the house accommodated all of our needs without feeling crowded. The hosts...
Sandalwood Retreat on Round Lake - Enjoy our screened porch & gorgeous sunsets 
Round Lake Roost—escape to A Summer Paradise!
Pool

Round Lake Roost—escape to A Summer Paradise!

10.0 out of 10, Exceptional, (70)
"This is a sweet spot. The house is clean, comfortable, and on a beautiful lake. The kitchen is as well stocked as any rental property we have stayed in (and we have stayed in quite a few) and the communication with the owner was excellent. The pictures are accurate and we loved our stay. Thanks for having us!"
Round Lake Roost—escape to A Summer Paradise!
Majestic views, classic charm, lifelong memories.
Exterior

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
Lake

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.
Interior

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!
Interior

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!
Hayward Home w/ Private Deck, Fire Pit & Kayak!
Fridge, microwave, stovetop, dishwasher

Hayward Home w/ Private Deck, Fire Pit & Kayak!

8.8 out of 10, Excellent, (5)
"Location was great for our ATV trip with friends. Place was clean. Nicely stocked with supplies. Lots of space for parking trucks and trailers. Aesthetically, decorated well. There is a plumbing/pipe issue that goes to the bathroom downstairs when the upstairs shower and toilet are used. This is an apparent ongoing issue that they plan to repair. Not pleasant to have water drilling from the ceiling all weekend. It’s damp and musty smelling downstairs due to likely mold growing. We...
Hayward Home w/ Private Deck, Fire Pit & Kayak!
Renovated cabin on Lac Courte Oreilles Lake - minutes from trails!
Fridge, microwave, oven, stovetop

Renovated cabin on Lac Courte Oreilles Lake - minutes from trails!

10.0 out of 10, Exceptional, (12)
"My Husband and I enjoyed our stay and would highly recommend staying here. It was the perfect spot for the two of us which is hard to find. Most accommodations are for larger groups and families. We were unable to use the fire pit due to high winds but we were able to sit on the dock enjoying our morning coffee and a glass of wine in the evening. We definitely would stay here again. "
The price is AU$588
includes taxes & fees
1 Dec - 2 Dec
Renovated cabin on Lac Courte Oreilles Lake - minutes from trails!
Bungalow Trail
Exterior

Bungalow Trail

9.8 out of 10, Exceptional, (40)
"Very cute place. "
Bungalow Trail
Scooter's Landing in Hinton Bay on Round Lake, the view is amazing!
Miscellaneous

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
Interior

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
Smart TV, video games, DVD player, table football

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
Wooded Lakefront Home: Nestled in the natural beauty of Birchwood, Wisconsin
Miscellaneous

Wooded Lakefront Home: Nestled in the natural beauty of Birchwood, Wisconsin

10.0 out of 10, Exceptional, (8)
"The property is just as described, and worked perfectly for 6 adults and 2 kids. The kitchen is stocked with pretty much anything you would need, and there were plenty of games/activities for the kids. Adults and kids loved playing Foosball and PacMan in the basement. There was plenty of room at the pier for all of our boats and we were able to take them out every day we were there. Communication was fantastic and any questions we had were answered very quickly. We had a great time. Thank...
Wooded Lakefront Home: Nestled in the natural beauty of Birchwood, Wisconsin
Little house in the woods but only 5 minutes from town!
Exterior

Little house in the woods but only 5 minutes from town!

9.8 out of 10, Exceptional, (17)
"Very nice place. Clean and just as advertised."
Little house in the woods but only 5 minutes from town!
THE 1852 LOG HOUSE.
Smart TV, fireplace, table football, books

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
TV, DVD player

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
Stone Mason`s Camp on the River | 3 Bed, 2 Bath
Fridge, microwave, oven, stovetop

Stone Mason`s Camp on the River | 3 Bed, 2 Bath

8.0 out of 10, Very good, (3)
"The small neighborhood it was in.......was rather odd.....but the cabin and the flowage were awesome!! Very quiet and peaceful"
Stone Mason`s Camp on the River | 3 Bed, 2 Bath
Special Pricing, 39% off For All New Bookings!
Fridge, microwave, oven, stovetop

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!
The Elk Inn on Lower Clam Lake - Beautiful New Cabin!
3 bedrooms, free WiFi, bed sheets

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!
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!
TV, fireplace, DVD player, table football

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
Exterior

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
Interior

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.
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