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Compare 99 Vacation Homes in Winter with updated reviews, rates, and availability.

North Fork Flambeau River near Park Falls, 3BR, 1BA country home, on ATV route.
Property grounds
North Fork Flambeau River near Park Falls, 3BR, 1BA country home, on ATV route.
10.0 out of 10, Exceptional, (2)
"The property, though older, has been well maintained and was spotless. There was plenty of space, and the view out the huge picture window over the water was spectacular. Communication with the host was great, and Michelle was so kind, especially when we couldn't get the door opened the first time. Other than coffee and wine, kitchen amenities are limited, but we had everything we needed to make simple meals. I have never seen so many bath amenities in my life. I enjoyed two soaks in the tub. My...
North Fork Flambeau River near Park Falls, 3BR, 1BA country home, on ATV route.
Spacious Lake Home near Ladysmith, with a private dock on the Dairyland Flowage!
Two Kayaks available for your use
Spacious Lake Home near Ladysmith, with a private dock on the Dairyland Flowage!
10.0 out of 10, Exceptional, (13)
"We enjoyed our stay in this home. The lake view we had was beautiful and even more beautiful because of the snow. We were in town for some family emergency services but we still enjoyed our time and felt very relaxed even with the family circumstances. We took lots of pictures and enjoyed every minute we could. The home is well stocked with pans and supplies."
Spacious Lake Home near Ladysmith, with a private dock on the Dairyland Flowage!
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, (33)
"One of the best rental experiences we have ever had. Hosts were wonderful in responding to questions and very helpful. Cabin was great, the game room was super fun and the kids are excited for our next visit! Thanks!"
Secluded 4-season cabin w/private waterfront, epic game room & mins from trails
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Lake Hayward. Private Lakefront Within Walking Distance To Downtown Hayward
Beautiful Sunset
Lake Hayward. Private Lakefront Within Walking Distance To Downtown Hayward
9.8 out of 10, Exceptional, (95)
"Great house, clean, comfortable bed, well-stocked, can’t beat the location, deer in the front yard & lake right out the back door! Good communication! Highly recommend!"
Lake Hayward. Private Lakefront Within Walking Distance To Downtown Hayward
Spacious Winter Retreat w/ River Access + Kayaks!
Winter Vacation Rental | 7BR | 4BA | 6,700 Sq Ft | Stairs Required
Spacious Winter Retreat w/ River Access + Kayaks!
8.6 out of 10, Excellent, (7)
"This was a great place to stay for a group of friends. The game room and bar area was a lot of fun. The property manager responded very quickly and was easy to work with. My only critique is that the kitchen area could use a bit of filling out, with effectively no consumables or spices available and an odd scattering of kitchen tools/pans, with heavy wear."
Spacious Winter Retreat w/ River Access + Kayaks!
Whispering Pines Hideaway overlooking peaceful Lake Gurno!
Living area
Whispering Pines Hideaway overlooking peaceful Lake Gurno!
10.0 out of 10, Exceptional, (44)
"Great place to stay for our family Memorial Day trip. Close enough to Hayward, and the property has everything you need to relax and have fun. Private dock plus a little beach on the property to build sand castles etc."
Whispering Pines Hideaway overlooking peaceful Lake Gurno!
6 bedroom 3- bath 16 people capacity pontoon included in Winter Wis.
Golf
6 bedroom 3- bath 16 people capacity pontoon included in Winter Wis.
10.0 out of 10, Exceptional, (43)
"We had a great week together as a family."
6 bedroom 3- bath 16 people capacity pontoon included in Winter Wis.
Bungalow Trail
Exterior
Bungalow Trail
9.8 out of 10, Exceptional, (32)
"This property was so clean and comfortable!! Everything we needed for our few days there during the American Birkebeiner!! Thank you and we will be back!! "
Bungalow Trail
Tri Lake Duplex House Side A and B with 6 bedrooms, 4 baths, 2 kitchens
Tri Lake Duplex House Side A and B with 6 bedrooms, 4 baths, 2 kitchens
Tri Lake Duplex House Side A and B with 6 bedrooms, 4 baths, 2 kitchens
Hayward Home w/ Private Deck, Fire Pit & Kayak!
Hayward Vacation Rental | 3BR | 2BA | 1,800 Sq Ft | 5 Steps Required to Enter
Hayward Home w/ Private Deck, Fire Pit & Kayak!
Hayward Home w/ Private Deck, Fire Pit & Kayak!
New Listing! Renovated cabin on Lac Courte Oreilles Lake - minutes from trails!
Dining
New Listing! Renovated cabin on Lac Courte Oreilles Lake - minutes from trails!
10.0 out of 10, Exceptional, (2)
"The hosts were very easy to work with. They made it super easy to check in and out. They also provided a lot of useful information about the area. Cabin is on a great spot on the lake with a beautiful view. A few steps down to the water. Rocky shoreline and the water was crystal clear. The cabin has been recently updated. Everything was VERY well done. We really enjoyed our stay and will be back again in the future."
New Listing! Renovated cabin on Lac Courte Oreilles Lake - minutes from trails!
Cozy Lake Home in Woods Near Hayward! Close Trails, Fishing, Fun Await!
Two spacious decks and a firepit overlooking the lake!
Cozy Lake Home in Woods Near Hayward! Close Trails, Fishing, Fun Await!
10.0 out of 10, Exceptional, (121)
"We had positive experiences with the host even before check in. Shawn was most responsive to any and all inquiries and willing to please. The house was perfect for four couples. It was comfortable for meals and conversation. Very well supplied and lots of information about the home and the area. If I could get our group to commit for a future stay, I’d definitely stay here again. Thank you, Shawn."
Cozy Lake Home in Woods Near Hayward! Close Trails, Fishing, Fun Await!
Lake home on beautiful private lake, 15 miles from downtown Hayward, WI
Outdoor patio and seating area for relaxing and eating outdoors
Lake home on beautiful private lake, 15 miles from downtown Hayward, WI
10.0 out of 10, Exceptional, (74)
"Great place to stay and relax. Owners are very accommodating."
Lake home on beautiful private lake, 15 miles from downtown Hayward, WI
Majestic views, classic charm, lifelong memories.
Exterior
Majestic views, classic charm, lifelong memories.
10.0 out of 10, Exceptional, (32)
"Top Shelf…Classic Location for Ice Fishing"
Majestic views, classic charm, lifelong memories.
Amazing Sunsets, Peaceful, Well Maintained Lake home on Beautiful, Barker lake
The Front Deck is a great way to enjoy the lake!
Amazing Sunsets, Peaceful, Well Maintained Lake home on Beautiful, Barker lake
9.6 out of 10, Exceptional, (54)
"Very nice, cozy stay. Lots of migrating birds with a lack of ice. Thanks again Kimberly for having us again"
Amazing Sunsets, Peaceful, Well Maintained Lake home on Beautiful, Barker lake
Eclectic Ladysmith Hideaway: Hike and Hunt!
Ladysmith Vacation Rental | 3BR | 1BA | 2 Stories | 1,100 Sq Ft
Eclectic Ladysmith Hideaway: Hike and Hunt!
10.0 out of 10, Exceptional, (18)
"My wife and I have stay here several times over this past year. Every stay has been wonderful and the property has a very homey feel. We are truly thankful for the opportunity to utilize this wonderful home. Thank you!"
Eclectic Ladysmith Hideaway: Hike and Hunt!
THE 1852 LOG HOUSE.
Exterior
THE 1852 LOG HOUSE.
9.8 out of 10, Exceptional, (25)
"We enjoyed the spacious cabin. Had everything we needed and more. Conveniently located near snowmobile/ATV trails. Hosts were gracious and quick to respond to questions. Would stay here again."
THE 1852 LOG HOUSE.
Beautiful round lake northern cedar modern vacation home
Our Home
Beautiful round lake northern cedar modern vacation home
9.4 out of 10, Exceptional, (31)
"This was a perfect location on the lake for us and what we wanted to do for the weekend."
Beautiful round lake northern cedar modern vacation home
"Ol Man Wavin Haven" home that has road access to UTV, ATV and snowmobile trails
Golf
"Ol Man Wavin Haven" home that has road access to UTV, ATV and snowmobile trails
10.0 out of 10, Exceptional, (1)
"Well laid out property, fully stocked kitchen, very clean and large. The lawn was well maintained and we saw some wild life! We will back."
"Ol Man Wavin Haven" home that has road access to UTV, ATV and snowmobile trails
Cozy log home on 6 acres - Hayward
Property grounds
Cozy log home on 6 acres - Hayward
10.0 out of 10, Exceptional, (106)
"This is a great place to stay with friends or family. There is great trails all around to ride. The cabin was so clean and relaxing, perfect for our trip!"
Cozy log home on 6 acres - Hayward
Don't see what you're looking for?
See all available properties in Winter
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.

Other property types in Winter

Spacious Winter Retreat w/ River Access + Kayaks!
Winter Vacation Rental | 7BR | 4BA | 6,700 Sq Ft | Stairs Required
Spacious Winter Retreat w/ River Access + Kayaks!
8.6 out of 10, Excellent, (7)
"This was a great place to stay for a group of friends. The game room and bar area was a lot of fun. The property manager responded very quickly and was easy to work with. My only critique is that the kitchen area could use a bit of filling out, with effectively no consumables or spices available and an odd scattering of kitchen tools/pans, with heavy wear."
Spacious Winter Retreat w/ River Access + Kayaks!
Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin
Interior
Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin
8.4 out of 10, Very Good, (11)
"A family owned business, the owner and his family made me feel very welcomed and looked after. It was a perfect place to relax and recharge."
Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin
Bears Den on the private lake
Exterior
Bears Den on the private lake
9.6 out of 10, Exceptional, (24)
"Everything went smooth. Nice place. Very involved owner that insured a pleasant stay."
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.

Recent reviews of Winter hotels
Expedia verified reviews

Newly Built Trailside Chalet in The Brook - direct access to CAMBA/Birkie Trails

Newly Built Trailside Chalet in The Brook - direct access to CAMBA/Birkie Trails

5/5 Excellent
Tranquil bliss
"Could not have chosen a nicer rental for a long weekend. Absolute peace and privacy, yet also close to town. Cabin was immaculate and comfortable. Watching turkeys run by while having morning coffee. Highest recommendation!"
A verified traveler stayed at Newly Built Trailside Chalet in The Brook - direct access to CAMBA/Birkie Trails
Posted 3 days ago
Newly Built Trailside Chalet in The Brook - direct access to CAMBA/Birkie Trails