Holiday rentals in Winter

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Top-rated holiday 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
29 Oct – 5 Nov
£90 per night
4.95 out of 5 average rating, 197 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.
4–11 JunIndividual Host,
£125 per night
4.92 out of 5 average rating, 309 reviews
Guest favourite
Cabin in Hayward
Hayward Haus, Modern Design w/ Classic Experience
Built as a winter or summer escape for a couple or small group, this beautiful four season cabin is a great way to experience the Northwoods of Wisconsin in a modern, well-appointed, aesthetically rich space designed with relaxation in mind. A heavy emphasis has been placed on style, comfort, usability of space, and privacy. Cabin is brand new as of August 2021. Host is 13 year "superhost" Note: Summer and Fall calendars have restrictions intended to eliminate one night calendar gaps.
31 Dec – 7 JanIndividual Host,
£294 per night
4.99 out of 5 average rating, 142 reviews

Popular amenities for Winter holiday rentals

Other great holiday rentals in Winter

Guest favourite
Cabin in Sarona
Hunt Hill's Rustic Log Cabin
13–20 JanProfessional Host,
£93 per night
4.93 out of 5 average rating, 219 reviews
Guest favourite
Cottage in Phillips
Charming Cottage on Wilson Lake
7–14 NovIndividual Host,
£131 per night
4.94 out of 5 average rating, 125 reviews
Guest favourite
Cabin in Solon Springs
Valley Red Cabin
21–28 Aug
£118 per night
4.97 out of 5 average rating, 145 reviews
Guest favourite
Guest house in Hayward
Seeley Chalet Ski-Bike-Hike
26 Jan – 2 FebIndividual Host,
£116 per night
4.99 out of 5 average rating, 318 reviews
Guest favourite
Guest house in Ojibwa
ATV/Side by Side enthusiasts! Private rd.
27 Aug – 3 Sept
£88 per night
4.96 out of 5 average rating, 45 reviews
Guest favourite
Home in Winter
Bungalow Trail
18–25 NovProfessional Host,
£112 per night
4.89 out of 5 average rating, 74 reviews
Guest favourite
Flat in Winter
Gateway to the Great North Woods by DonBar
24 Sept – 1 OctIndividual Host,
£107 per night
4.96 out of 5 average rating, 98 reviews
Guest favourite
Cabin in Winter
The Hideaway on Highland
24 Apr – 1 MayIndividual Host,
£227 per night
5.0 out of 5 average rating, 11 reviews
Guest favourite
Cabin in Winter
Lakefront cabin on Connor’s Lake, sleeps 6, WiFi
25 Apr – 2 May
£145 per night
4.96 out of 5 average rating, 27 reviews
Guest favourite
Cabin in Winter
Bobbers Cabin on Private Lake
13–20 DecIndividual Host,
£200 per night
5.0 out of 5 average rating, 14 reviews
Superhost
Cabin in Winter
Northwoods Cabin
23–30 Aug
£190 per night
4.9 out of 5 average rating, 21 reviews
Guest favourite
Cabin in Ojibwa
Sauna Rental, Game Table, Fireplace, 2 King Beds
17–24 AprIndividual Host,
£139 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