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Compare 51 Cottages in Winter with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (114)
"We had an absolutely wonderful stay in The North Woods! Beautiful house with lots of comforts, loved all the games for kids! Greta was very easy to communicate with. Would stay there again! "
Family Friendly Cottage w/Spectacular Views of Round Lake-Hayward, WI

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

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

9.6 out of 10, Exceptional, (5)
"I like the town alot ."
Winter Nights Cottages: Cottage 5 Winter, Wisconsin vacation rental.

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!

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

9.6 out of 10, Exceptional, (11)
"Your place worked great for our group on our last night in the Northwoods!"
The price is SAR 409
SAR 530 total
includes taxes & fees
30 Mar - 31 Mar
Lakefront cottage w/ convenient access to restaurants, atv and snowmobile trails

Fresh snow, available Birkie!-King Bed, Pacman, EV

10.0 out of 10, Exceptional, (6)
"We had a lovely stay. Easy to get to town or other activities. Owners were very responsive. Beds were very comfortable. A very nice place to hang out and relax as a family. "
The price is SAR 766
SAR 1,204 total
includes taxes & fees
20 Mar - 21 Mar
Fresh snow, available Birkie!-King Bed, Pacman, EV

Snowmobile base camp to Tuscobia Tr! Private cottage and access to trails! Dogs!

10.0 out of 10, Exceptional, (25)
"Perfect accommodations for the activities in Hayward and Cable. Cabin was easily accessible, comfortably furnished, toasty warm, and exceedingly well equipped. Highly recommended getaway spot for any season."
Snowmobile base camp to Tuscobia Tr! Private cottage and access to trails! Dogs!

Butler's Bay Cottage on Teal Lake with Private Dock

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 on Teal Lake with Private Dock

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, (5)
"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

Ladysmith Cozy Cottage - Copper Tub - Waterfront

2.0 star property
10.0 out of 10, Exceptional, (2)
"Booked this place for me and my girlfriend to get away, relax, and recharge after the holidays. This Cozy Cottage was just the thing. We had a fantastic time and everything was as advertised. Would recommend this place to anyone looking to visit the Ladysmith, WI area."
The price is SAR 573
SAR 999 total
includes taxes & fees
20 Mar - 21 Mar
Ladysmith Cozy Cottage - Copper Tub - Waterfront

Winter Nights Cottages: Cottage 4 Winter, Wisconsin vacation rental

10.0 out of 10, Exceptional, (6)
"We loved our stay at Winter Nights Cottages! Our check-in process was a breeze and the cottage was just what we had imagined (and more). Super clean, well taken care of, and had everything we needed. 10/10 recommend and will definitely be returning! Thank you!"
Winter Nights Cottages: Cottage 4 Winter, Wisconsin vacation rental

Winter Nights Cottages: Cottage 3 Winter, Wisconsin vacation rental.

8.8 out of 10, Excellent, (3)
"Strong pet odor inside and on sheets etc. Recommend a stronger laundry detergent to cut smell. "
Winter Nights Cottages: Cottage 3 Winter, Wisconsin vacation rental.

Winter Nights Cottages: Cottage 1 Winter, Wisconsin vacation rental.

9.0 out of 10, Wonderful, (2)
"Been staying in the winter area for over 40 years.by far the best place yet ! Convenient and clean and easy to book "
Winter Nights Cottages: Cottage 1 Winter, Wisconsin vacation rental.

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!

Lakefront Wisconsin Cabin With Boat Dock!

3.0 star property
Lakefront Wisconsin Cabin With Boat Dock!

Hayward Cabin w/ Boat Slip + Fish House!

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

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

Eclectic Ladysmith Hideaway: Hike and Hunt!

3.0 star property
Eclectic Ladysmith Hideaway: Hike and Hunt!
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

Luxury Cabin, 800+ feet frontage, 733 acre Lake, Hot tub, Pontoon, Fireplace .

10.0 out of 10, Exceptional, (19)
"Highly recommend for a Wisconsin North Woods getaway. Luxurious accommodations in a serene environment, very close to a village with basic amenities "
Luxury Cabin, 800+ feet frontage, 733 acre Lake, Hot tub, Pontoon, Fireplace .

Spacious Winter Retreat w/ River Access + Kayaks!

9.2 out of 10, Wonderful, (19)
"Perfect cabin in the woods! Has a great scenic spot on the river and plenty of space for guests. Awesome game room and bar area as advertised. Teresa was a great host and was very helpful throughout the process. Would definitely come back! "
Spacious Winter Retreat w/ River Access + Kayaks!

Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

8.8 out of 10, Excellent, (17)
"Owner made the check in process a breeze. Quaint and great spot in a nice location, definitely will be staying again. Thank you Bucktail Lodge! "
Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin
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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How can I find cheap cottages in Winter?
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