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

4.95 out of 5 average rating, 199 reviews

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

3–10 Feb

£90 per night
Guest favourite

Guest house in Hayward

5.0 out of 5 average rating, 104 reviews

Silent Sports Retreat in Seeley

The dog-friendly Hollywood Hills Chalet is a charming guest cabin that provides opportunities to ski, snowshoe, fat bike, MTB and hike out the door on our neighborhood trail network that is groomed in the winter. In warmer weather, the Namekagon River is less than a mile away and nearby Silverthorn Lake Park in Seeley offers great opportunities to paddle, or just chill on a family-friendly beach. Parking for 2-3 vehicles and a smaller standard trailer. (Nonsmokers only, please and thank you.)

9–16 Apr

£93 per night
Superhost

Cottage in Medford

4.84 out of 5 average rating, 296 reviews

Cozy A-frame on Clear Lake

Relax and enjoy the slower pace of lake life. Catch pan fish from the dock or kayak the chain of lakes! Water not your thing? Use our Cozy A-frame as the base camp for your summer UTV trip or winter snowmobile fun, we sit right on the trail systems. This cozy A-frame built in 2005 features a fireplace, tile floor, full bath and loft area that sleeps 5. Located on Clear Lake near Medford in north central Wisconsin, just down the road from 2 supper clubs and a general store with gas pump.

3–10 Sept

£122 per night

Popular amenities for Winter holiday rentals

Other great holiday rentals in Winter

Guest favourite

Tiny home in Lake Nebagamon

4.97 out of 5 average rating, 348 reviews

Berrywood Acres Cabin

13–20 Sept

£117 per night
Guest favourite

Cabin in Trego

4.99 out of 5 average rating, 194 reviews

Wilderness River Boat House

13–20 May

£86 per night
Guest favourite

Tiny home in Lake Nebagamon

4.98 out of 5 average rating, 312 reviews

Deer Haven - Cozy Northwoods Tiny House

19–26 Aug

£103 per night
Guest favourite

Home in Winter

4.89 out of 5 average rating, 74 reviews

Bungalow Trail

28 Aug – 4 Sept

£112 per night
Guest favourite

Guest house in Ojibwa

4.96 out of 5 average rating, 45 reviews

ATV/Side by Side enthusiasts! Private rd.

25 Nov – 2 Dec

£92 per night
Guest favourite

Flat in Winter

4.96 out of 5 average rating, 98 reviews

Gateway to the Great North Woods by DonBar

27 Nov – 4 Dec

£107 per night
Guest favourite

Cabin in Winter

5.0 out of 5 average rating, 14 reviews

Bobbers Cabin on Private Lake

6–13 Sept

£171 per night
Guest favourite

Cabin in Winter

5.0 out of 5 average rating, 11 reviews

The Hideaway on Highland

27 Feb – 6 Mar

£229 per night
Superhost

Cabin in Winter

4.91 out of 5 average rating, 22 reviews

Northwoods Cabin

1–8 Jun

£207 per night
Guest favourite

Cabin in Winter

4.96 out of 5 average rating, 27 reviews

Lakefront cabin on Connor’s Lake, sleeps 6, WiFi

12–19 Feb

£186 per night
Guest favourite

Cabin in Bruce

4.95 out of 5 average rating, 19 reviews

Winding Creek Cabin - next to Christie Mountain!

9–16 Sept

£129 per night
Guest favourite

Home in Park Falls

4.95 out of 5 average rating, 60 reviews

Our North Woods Getaway

18–25 Oct

£130 per night

Destinations to explore

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