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Check prices for these dates

Next weekend
9 Jum. I - 11 Jum. I
In two weeks
16 Jum. I - 18 Jum. I
In one month
30 Jum. I - 1 Jum. II
In two months
27 Jum. II - 29 Jum. II

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

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)
"A VERY NICE CABIN ON THE FLOWAGE"
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) | Interior

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)
"The view is fantastic ...loved sitting in the living room and enjoying the lake. The location is convenient for accessing all the area has to offer. "
The price is SAR 446
SAR 571 total
includes taxes & fees
30 Apr - 1 May
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)
"Great cabin, great lake, great town, great host!"
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)
"Wonderful place to stay.! Beautifully lake to kayak on."
The price is SAR 871
SAR 1,335 total
includes taxes & fees
30 Apr - 1 May
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)
"Very nice owner, was accommodating to our needs. Very nice cabin. Would stay there again."
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)
"Great place to stay! Nice and quiet with great views over the lake. I will definitely book this place again."
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)
"A perfect location for fishing on Lake Winter"
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
30 Apr - 1 May
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)
"Cozy & affordable place to stay with plenty of room for more than two people if needed. I loved that it was pet friendly even though we didn’t not end up bringing our dog. We had everything we needed for our stay. Winter is a must stay place for fishing, UTV riding & simply enjoying the town! We will definitely be coming to stay again!"
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!
Stone Lake Cabin: Grill & Access to Fishing!
Miscellaneous

Stone Lake Cabin: Grill & Access to Fishing!

3.0 star property
Stone Lake Cabin: Grill & Access to Fishing!
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
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, (54)
"Owners thought of everything we could possibly need. The game room was great for the kids as well as the adults. The pontoon was great and we loved the screened in porch"
6 bedroom 3- bath 16 people capacity pontoon included in Winter Wis.
Bears Den on the private lake
Interior

Bears Den on the private lake

9.6 out of 10, Exceptional, (26)
"Well outfitted cabin - had a group of 10 and had plenty of space, cooking-ware, and plates. Hosts were very responsive. Kids enjoyed splashing in the water and swimming back and forth from the swim platform. Would stay again."
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.