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Compare 39 Cottages in Winter with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (22)
"We had a great trip. We put on 300 plus miles Got to see a bear and a wolf and and a bunch of turkeys and deer while out riding The cabin is set up very well plenty of room will look at staying there again in the future Thanks "
ATV riders! Private wooded lot, cottage access to trails! Dogs! Firepit!

Thanksgiving Lake Cottage-King Bed, Pacman, EV

10.0 out of 10, Exceptional, (5)
"My wife and I stayed for a long weekend in the beginning of October. The leaves were changing for fall and the weather was perfect! The hot tub and kayaks were a great addition. We would definitely come back again!"
The price is SAR 710
SAR 1,090 total
includes taxes & fees
4 Dec - 5 Dec
Thanksgiving Lake Cottage-King Bed, Pacman, EV

private setting and right on the lake!

10.0 out of 10, Exceptional, (24)
"It was a very good pleasant place that was very clean and easy to get to."
private setting and right on the lake!

Phillips Cabin w/ Lake Views & Private Dock!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Nice house on lake with private dock. Try cafe in town reasonable prices nice portions and friendly service "
Phillips Cabin w/ Lake Views & Private Dock!

Wisconsin Lakeside Cottage w/ Deck, Views

3.0 star property
Wisconsin Lakeside Cottage w/ Deck, Views

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

10.0 out of 10, Exceptional, (112)
"Read above "
Family Friendly Cottage w/Spectacular Views of Round Lake-Hayward, WI

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

9.6 out of 10, Exceptional, (10)
"Your place worked great for our group on our last night in the Northwoods!"
The price is SAR 601
SAR 748 total
includes taxes & fees
1 Dec - 2 Dec
Lakefront cottage w/ convenient access to restaurants, atv and snowmobile trails

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

9.0 out of 10, Wonderful, (4)
"Had a nice weekend of fishing, and the cabin worked great for our family's needs. Would certainly stay again!"
Butler's Bay Cottage with 34% off until the end of September!

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

8.0 out of 10, Very Good, (6)
"Great little cabin, great location with great views out every window, a little ruff on the edges. We did chose this cabin because of the hot tub over other's and there wasn't one. I feel like we taken. really didn't get what we paid for."
Bucktail Lodge Bayview Cabin, view of the East Fork of the Chippewa flowage

Beautiful sunsets, water access, close to trails, Wi-Fi, sml dogs

10.0 out of 10, Exceptional, (10)
"The place was gorgeous it was tucked in a little wooded area surrounded by lake Chippewa the house was immaculate not a dust bunny in sight and I have OCD so you know this was a very clean place. They have every comfort you can have an array of board games and so many different outside games such as corn whole kickball and don't get me started on the cute pattle boat and kayaks this is definitely a beautiful place to take your family and friends if you want to escape the hustle and bustle of the...
Beautiful sunsets, water access, close to trails, Wi-Fi, sml dogs

The Cabin- cozy cottage on the sandy shores of the Chippewa Flowage

9.6 out of 10, Exceptional, (4)
"We (family of 5) stayed a week in what will undoubtedly be the warmest week of the year. The cabin is great and you could sense that it has been a beloved destination for the family that has owned it for many decades. It is very comfortable and I'd love to visit in the fall. The kitchen is well-appointed such that you don't need to bring anything typically found in one. Gas grill worked fine and there were 2 tanks, so no worries. Beds were comfortable. Tap water was hot and tasted fine. The...
The Cabin- cozy cottage on the sandy shores of the Chippewa Flowage

A-frame Cabin w/ Private Boat Dock!

3.0 star property
A-frame Cabin w/ Private Boat Dock!

Cozy Hayward Cottage w/ Dock & Lakefront View

10.0 out of 10, Exceptional, (4)
"The cabin was clean and big then I expected. Maybe move the TV a different spot or a little left by the table though. It was quiet all the time we went. We catched a lot of fish. Large bass, pike, crappie, bluegill and two muskie!. I recommended the cabin."
Cozy Hayward Cottage w/ Dock & Lakefront View

Convenient Cabin w/ Access to 3 Boat Docks!

2.0 star property
8.0 out of 10, Very Good, (1)
"Only issue was no coin machine to play pool. Didn’t know we would need them, but should be posted. "
Convenient Cabin w/ Access to 3 Boat Docks!

Stone Lake Cabin w/ Private Deck & Fire Pit!

2.0 star property
10.0 out of 10, Exceptional, (1)
Stone Lake Cabin w/ Private Deck & Fire Pit!

Stone Lake Cabin: Grill & Access to Fishing!

3.0 star property
Stone Lake Cabin: Grill & Access to Fishing!

Eclectic Ladysmith Hideaway: Hike and Hunt!

3.0 star property
Eclectic Ladysmith Hideaway: Hike and Hunt!

Hayward Cabin w/ Boat Slip + Fish House!

2.0 star property
Hayward Cabin w/ Boat Slip + Fish House!

Butler's Bay Cottage 2 Bedroom Cottage by RedAwning

3.0 star property
Butler's Bay Cottage 2 Bedroom Cottage by RedAwning

Lakefront Wisconsin Cabin With Boat Dock!

3.0 star property
Lakefront Wisconsin Cabin With Boat Dock!
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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Other property types in Winter

Spacious Winter Retreat w/ River Access + Kayaks!

9.0 out of 10, Wonderful, (17)
"This has been the second year we’ve been here. It’s a great place for a large group with plenty of space for everyone! This will continue to be our go to spot for years to come! "
Spacious Winter Retreat w/ River Access + Kayaks!

Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

8.8 out of 10, Excellent, (16)
"Newer owner is showing improvement to property."
Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

Bears Den on the private lake

9.6 out of 10, Exceptional, (26)
"The lake was great and the living situation for our large group was very comfortable. The only reason I give it 4 stars is because there was no hot water. The showers were absolutely freezing. Besides that everything was great."
Bears Den on the private lake
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.

Frequently asked questions

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Reserving a cottage in Winter is as simple as working out your travel dates and picking an ideal place for outdoor fun and relaxation. From upscale retreats to budget-friendly stays and cottages that feature amenities like laundry facilities, Expedia has something for all styles and tastes. As for unbeatable deals? We’ve got them too!
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