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.
Home in Ladysmith
4.95 out of 5 average rating, 199 reviewsNorth 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
Guest house in Hayward
5.0 out of 5 average rating, 104 reviewsSilent 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
Cottage in Medford
4.84 out of 5 average rating, 296 reviewsCozy 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
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Winter holiday rentals
Other great holiday rentals in Winter
Tiny home in Lake Nebagamon
4.97 out of 5 average rating, 348 reviewsBerrywood Acres Cabin
13–20 Sept
Cabin in Trego
4.99 out of 5 average rating, 194 reviewsWilderness River Boat House
13–20 May
Tiny home in Lake Nebagamon
4.98 out of 5 average rating, 312 reviewsDeer Haven - Cozy Northwoods Tiny House
19–26 Aug
Home in Winter
4.89 out of 5 average rating, 74 reviewsBungalow Trail
28 Aug – 4 Sept
Guest house in Ojibwa
4.96 out of 5 average rating, 45 reviewsATV/Side by Side enthusiasts! Private rd.
25 Nov – 2 Dec
Flat in Winter
4.96 out of 5 average rating, 98 reviewsGateway to the Great North Woods by DonBar
27 Nov – 4 Dec
Cabin in Winter
5.0 out of 5 average rating, 14 reviewsBobbers Cabin on Private Lake
6–13 Sept
Cabin in Winter
5.0 out of 5 average rating, 11 reviewsThe Hideaway on Highland
27 Feb – 6 Mar
Cabin in Winter
4.91 out of 5 average rating, 22 reviewsNorthwoods Cabin
1–8 Jun
Cabin in Winter
4.96 out of 5 average rating, 27 reviewsLakefront cabin on Connor’s Lake, sleeps 6, WiFi
12–19 Feb
Cabin in Bruce
4.95 out of 5 average rating, 19 reviewsWinding Creek Cabin - next to Christie Mountain!
9–16 Sept
Home in Park Falls
4.95 out of 5 average rating, 60 reviewsOur North Woods Getaway
18–25 Oct
Destinations to explore
- Duluth Holiday rentals
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