Hot Winter Cottage Rates

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Featured Cottages in Winter

Winter Nights Cottages: Cottage 5 Winter, Wisconsin vacation rental.

Winter Nights Cottages: Cottage 5 Winter, Wisconsin vacation rental.

Winter
With a stay at this cottage in Winter, you'll be within a 10-minute walk of Winter Public Library and Doc Smith Park.
Winter Nights Cottages: Cottage 5 Winter, Wisconsin vacation rental.
Phillips Cabin w/ Lake Views & Private Dock!

Phillips Cabin w/ Lake Views & Private Dock!

3 out of 5
Phillips
When you stay at this cottage in Phillips, you'll be 8 minutes by car from Solberg Lake.
Phillips Cabin w/ Lake Views & Private Dock!
Family Friendly Cottage w/Spectacular Views of Round Lake-Hayward, WI

Family Friendly Cottage w/Spectacular Views of Round Lake-Hayward, WI

Hayward
When you a stay at this cottage in Hayward, you'll be on the waterfront, within a 5-minute walk of Round Lake and Lake Placid.
Family Friendly Cottage w/Spectacular Views of Round Lake-Hayward, WI
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Lakefront cottage w/ convenient access to restaurants, atv and snowmobile trails

Lakefront cottage w/ convenient access to restaurants, atv and snowmobile trails

Phillips
The price is AU$231 per night from 6 Jan to 7 Jan
AU$231
includes taxes & fees
6 Jan - 7 Jan 2025
Located in Phillips, this cottage is on the waterfront, within a 5-minute drive of Lidice Memorial and Wisconsin Concrete Park.
Lakefront cottage w/ convenient access to restaurants, atv and snowmobile trails
Available Birkie!-King Bed, Pacman, EV

Available Birkie!-King Bed, Pacman, EV

Hayward
The price is AU$647 per night from 24 Dec to 25 Dec
AU$647
includes taxes & fees
24 Dec - 25 Dec
Located in Hayward, this cottage is on the waterfront, within a 15-minute drive of Spider Lake Townhall and Round Lake.
Available Birkie!-King Bed, Pacman, EV
ATV riders! Private wooded lot, cottage access to trails! Dogs! Firepit!

ATV riders! Private wooded lot, cottage access to trails! Dogs! Firepit!

Ojibwa
Located in Ojibwa, this cottage is in a rural location, within a 15-minute drive of Ojibwa State Park and Doc Smith Park.
ATV riders! Private wooded lot, cottage access to trails! Dogs! Firepit!
Butler's Bay Cottage with 34% off until the end of September!

Butler's Bay Cottage with 34% off until the end of September!

Hayward
With a stay at this cottage in Hayward, you'll be on the waterfront, just a 1-minute walk from Chequamegon National Forest and 11 minutes by foot from Loon ...
Butler's Bay Cottage with 34% off until the end of September!
private setting and right on the lake!

private setting and right on the lake!

Phillips
When you stay at this cottage in Phillips, you'll be on the waterfront and 8 minutes by car from Solberg Lake.
private setting and right on the lake!
Bucktail Lodge Bayview Cabin, view of the East Fork of the Chippewa flowage

Bucktail Lodge Bayview Cabin, view of the East Fork of the Chippewa flowage

Winter
With a stay at this cottage in Winter, you'll be just steps from Chequamegon National Forest and Barker Lake.
Bucktail Lodge Bayview Cabin, view of the East Fork of the Chippewa flowage
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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.

Winter Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in Winter will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to Winter definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in Winter, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Winter Cottages essential information

Accommodation
43 Cottages
Lowest Price
AU$231
Highest Price
AU$647
Popular accommodation
Winter Nights Cottages: Cottage 5 Winter, Wisconsin vacation rental., Phillips Cabin w/ Lake Views & Private Dock!, Family Friendly Cottage w/Spectacular Views of Round Lake-Hayward, WI, Lakefront cottage w/ convenient access to restaurants, atv and snowmobile trails, Available Birkie!-King Bed, Pacman, EV, ATV riders! Private wooded lot, cottage access to trails! Dogs! Firepit!, Butler's Bay Cottage with 34% off until the end of September!, private setting and right on the lake!, Bucktail Lodge Bayview Cabin, view of the East Fork of the Chippewa flowage

Top trending hotels in Winter

Spacious Winter Retreat w/ River Access + Kayaks!

Spacious Winter Retreat w/ River Access + Kayaks!

Winter
With a stay at this vacation home in Winter, you'll be within a 15-minute drive of Ojibwa State Park and Doc Smith Park.
Spacious Winter Retreat w/ River Access + Kayaks!
Bears Den on the private lake

Bears Den on the private lake

Winter
When you a stay at this vacation home in Winter, you'll be on the waterfront, within a 5-minute walk of Chequamegon National Forest and Perch Lake.
Bears Den on the private lake
Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

Winter
When you a stay at this cabin in Winter, you'll be on the waterfront, just steps from Chequamegon National Forest and Barker Lake.
Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin
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Holiday Inn Express & Suites Hayward, an IHG Hotel

Holiday Inn Express & Suites Hayward, an IHG Hotel

2.5 out of 5
15586 County Road B, Hayward, WI
Fully refundable
The price is AU$244 per night from 1 Jan to 2 Jan
AU$244
includes taxes & fees
1 Jan - 2 Jan 2025
Holiday Inn Express & Suites Hayward, an IHG Hotel is centrally located in Hayward, a 4-minute walk from Hayward Lake and 10 minutes by foot from National Fresh ...
Holiday Inn Express & Suites Hayward, an IHG Hotel
Don't see what you're looking for?
See all available properties in Winter
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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.

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^Subject to availability and chosen travel dates.