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Check prices for these dates

Next weekend
18 Rab. II - 20 Rab. II
In two weeks
25 Rab. II - 27 Rab. II
In one month
9 Jum. I - 11 Jum. I
In two months
6 Jum. II - 8 Jum. II

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

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

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

10.0 out of 10, Exceptional, (11)
"We give this property 5 stars all around.We stay for 4 days in march 2025.This place was so clean and well taken care of.The owner thought of everything you could need for an enjoyable stay."
Beautiful sunsets, water access, close to trails, Wi-Fi, sml dogs
The Cabin- cozy cottage on the sandy shores of the Chippewa Flowage
Private kitchen

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.
Exterior

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!
House (2 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

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
Property grounds

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 372
SAR 489 total
includes taxes & fees
8 Apr - 9 Apr
Lakefront cottage w/ convenient access to restaurants, atv and snowmobile trails
Family Friendly Cottage w/Spectacular Views of Round Lake-Hayward, WI
Interior

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
Butler's Bay Cottage on Teal Lake with Private Dock
Exterior

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
Fresh snow, available Birkie!-King Bed, Pacman, EV
Terrace/patio

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 709
SAR 1,142 total
includes taxes & fees
8 Apr - 9 Apr
Fresh snow, available Birkie!-King Bed, Pacman, EV
Your base camp to Tuscobia Tr! Private cottage and access to trails! Dogs!
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (26)
"We had a great weekend and your cabin was perfect. We will highly recommend!!"
Your base camp to Tuscobia Tr! Private cottage and access to trails! Dogs!
A-frame Cabin w/ Private Boat Dock!
Microwave, oven, stovetop, blender

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
Aerial view

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
Winter Nights Cottages: Cottage 4 Winter, Wisconsin vacation rental
Exterior

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
Ladysmith Cozy Cottage - Copper Tub - Waterfront
Smart TV, fireplace

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 574
SAR 1,008 total
includes taxes & fees
8 Apr - 9 Apr
Ladysmith Cozy Cottage - Copper Tub - Waterfront
Winter Nights Cottages: Cottage 3 Winter, Wisconsin vacation rental.
Exterior

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.
Exterior

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!
Property grounds

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!
TV, fireplace

Lakefront Wisconsin Cabin With Boat Dock!

3.0 star property
Lakefront Wisconsin Cabin With Boat Dock!
Hayward Cabin w/ Boat Slip + Fish House!
Interior

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
Cottage, 2 Bedrooms | Exterior

Butler's Bay Cottage 2 Bedroom Cottage by RedAwning

3.0 star property
Butler's Bay Cottage 2 Bedroom Cottage by RedAwning
Eclectic Ladysmith Hideaway: Hike and Hunt!
Interior

Eclectic Ladysmith Hideaway: Hike and Hunt!

3.0 star property
10.0 out of 10, Exceptional, (1)
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

Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin
Exterior

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
Luxury Cabin, 800+ feet frontage, 733 acre Lake, Hot tub, Pontoon, Fireplace .
Fridge, microwave, oven, stovetop

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 .
6 bedroom 3- bath 16 people capacity pontoon included in Winter Wis.
Sun loungers, beach towels

6 bedroom 3- bath 16 people capacity pontoon included in Winter Wis.

9.8 out of 10, Exceptional, (53)
"WILL NEED TO GO BACK IN THE SUMMER TO ENJOY THE LAKE "
6 bedroom 3- bath 16 people capacity pontoon included in Winter Wis.
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

Why book your cottage in Winter with Expedia?
Expedia has some terrific cottages in Winter, so start planning for an unforgettable vacation on nature’s doorstep. If you have a set budget, click on how much you want to spend and the preferred star rating of your property. Or take advantage of our filters to search for cottages with free WiFi or a kitchen. We’ll help you find the right place whatever your plans or bank balance.
How can I find cheap cottages in Winter?
A good way to track down cheap cottages in Winter is with Expedia’s handy filter tool. Narrow down your search results by budget, star rating and amenities to discover awesome rates with only a few clicks.