Vacation rentals in Winter

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Top-rated vacation rentals in Winter

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Home in Ladysmith
North Country Cottage
This beautiful, recently renovated home is out in the country down a dead-end road, but still only a few miles from the town of Ladysmith. It is about a mile from a little county park on the Dairyland Reservoir, only a few miles from the local golf course, and just down the road from hopping on the snowmobile trail in the winter. There is a boat landing at the park for summer and access to ice fishing in the winter. We hope to earn 5*s and look forward to hosting you! State License #VJAS-BCCLDB
Jan. 17 – 24
$154 CAD per night
4.95 out of 5 average rating, 197 reviews
Guest favourite
Cabin in Hayward
Cozy 2 bedroom cabin on the water - must see!!
Enjoy a quiet, relaxing week in the north woods of Hayward, WI! Our 2 bedroom, 2 bath cabin sleeps six comfortably (queen, 2 single beds and a futon). Cabin is two levels and 1500 square ft. The cabin is located on the Namekagon River with direct access to Hayward Lake and the public boat launch just a few hundred feet away. You really get the best of both worlds here as the cabin is tucked away in a private, wooded area but is also walking distance to downtown Hayward and other attractions!!
Mar. 30 – Apr. 6
$190 CAD per night
4.96 out of 5 average rating, 130 reviews
Guest favourite
Cabin in Ladysmith
Flaming Torch Lodge (No Cleaning Fee)
This is a quaint little cabin on the Flambeau River just outside of Ladysmith, WI (flambeau translastes to flaming torch) It is a clean space with rustic charm. It has a fully equipped kitchen, stove and fridge. A gas fireplace is the centerpiece of the living room. Snuggle up on the sofa or recliner, turn on the fireplace, and relax. There is one bedroom with a memory foam mattress. A loft with a sleeper couch. Free amenities, including cleaning. No pets and no smoking at any time please.
Sep. 12 – 19
$175 CAD per night
4.92 out of 5 average rating, 309 reviews

Popular amenities for Winter vacation rentals

Other great vacation rentals in Winter

Guest favourite
Home in Mason
Marengo River Cabin
Nov. 25 – Dec. 2
$245 CAD per night
4.94 out of 5 average rating, 231 reviews
Guest favourite
Home in Phillips
PINE PLACE engage with the outdoors
Sep. 22 – 29
$128 CAD per night
4.91 out of 5 average rating, 222 reviews
Guest favourite
Cabin in Hayward
Hayward Haus, Modern Design w/ Classic Experience
Jul. 21 – 28
$796 CAD per night
4.99 out of 5 average rating, 142 reviews
Guest favourite
Cabin in Solon Springs
Valley Red Cabin
Jan. 2 – 9
$202 CAD per night
4.97 out of 5 average rating, 145 reviews
Guest favourite
Guesthouse in Ojibwa
ATV/Side by Side enthusiasts! Private rd.
Aug. 26 – Sep. 2
$151 CAD per night
4.96 out of 5 average rating, 45 reviews
Guest favourite
Home in Winter
Bungalow Trail
Apr. 15 – 22
$191 CAD per night
4.89 out of 5 average rating, 73 reviews
Guest favourite
Apartment in Winter
Gateway to the Great North Woods by DonBar
Sep. 12 – 19
$183 CAD per night
4.96 out of 5 average rating, 98 reviews
Guest favourite
Cabin in Winter
Lakefront cabin on Connor’s Lake, sleeps 6, WiFi
Apr. 24 – May 1
$248 CAD per night
4.96 out of 5 average rating, 27 reviews
Guest favourite
Cabin in Winter
Bobbers Cabin on Private Lake
Nov. 17 – 24
$328 CAD per night
5.0 out of 5 average rating, 14 reviews
Guest favourite
Cabin in Winter
The Hideaway on Highland
Apr. 23 – 30
$388 CAD per night
5.0 out of 5 average rating, 11 reviews
Superhost
Cabin in Winter
Northwoods Cabin
Jan. 7 – 14
$346 CAD per night
4.9 out of 5 average rating, 21 reviews
Guest favourite
Cabin in Ojibwa
Sauna Rental, Game Table, Fireplace, 2 King Beds
Oct. 22 – 29
$288 CAD per night
4.94 out of 5 average rating, 69 reviews

Destinations to explore

  1. Airbnb
  2. United States
  3. Wisconsin
  4. Sawyer County
  5. Winter