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Check prices for these dates

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Compare 43 Cottages in Winter with updated reviews, rates, and availability.

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

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

10.0 out of 10, Exceptional, (113)
"This was our second time staying here and we will be back! Such an accommodating cabin. The views of the lake are beautiful, so serene and quiet.It’s immaculately, clean and stashed with anything we could possibly need. There are drawers with board games.The sunroom is a perfect spot to play games and read as a family. The basement ping pong table and dart board are an added bonus. Greta is a wonderful host and we can’t wait to be back!"
Family Friendly Cottage w/Spectacular Views of Round Lake-Hayward, WI
The Cabin- cozy cottage on the sandy shores of the Chippewa Flowage
Exterior

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!
Living area

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 409
SAR 530 total
includes taxes & fees
24 Feb - 25 Feb
Lakefront cottage w/ convenient access to restaurants, atv and snowmobile trails
A-frame Cabin w/ Private Boat Dock!
Exterior

A-frame Cabin w/ Private Boat Dock!

3.0 star property
A-frame Cabin w/ Private Boat Dock!
Fresh snow, available Birkie!-King Bed, Pacman, EV
Acorn Shores cottage is the perfect location for a fall or winter getaway near Haywards 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 838
SAR 1,292 total
includes taxes & fees
5 Mar - 6 Mar
Fresh snow, available Birkie!-King Bed, Pacman, EV
Cozy Hayward Cottage w/ Dock & Lakefront View
Hayward Vacation Rental | 3BR | 2BA | 1,800 Sq Ft | Stairs Required

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

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

10.0 out of 10, Exceptional, (24)
"Nice, new place to stay. We stayed plenty warm during a cold hunting weekend "
Snowmobile base camp to Tuscobia Tr! Private cottage and access to trails! Dogs!
Beautiful sunsets, water access, close to trails, Wi-Fi, sml dogs
Exterior detail

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
Ladysmith Cozy Cottage - Copper Tub - Waterfront
Room

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
24 Feb - 25 Feb
Ladysmith Cozy Cottage - Copper Tub - Waterfront
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
Butler's Bay Cottage on Teal Lake with Private Dock
View From Lake

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
private setting and right on the lake!
Living area

private setting and right on the lake!

10.0 out of 10, Exceptional, (25)
"It was a very good pleasant place that was very clean and easy to get to."
private setting and right on the lake!
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.
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.
Lakefront Wisconsin Cabin With Boat Dock!
Living area

Lakefront Wisconsin Cabin With Boat Dock!

3.0 star property
Lakefront Wisconsin Cabin With Boat Dock!
Eclectic Ladysmith Hideaway: Hike and Hunt!
Living area

Eclectic Ladysmith Hideaway: Hike and Hunt!

3.0 star property
Eclectic Ladysmith Hideaway: Hike and Hunt!
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!
Wisconsin Lakeside Cottage w/ Deck, Views
Terrace/patio

Wisconsin Lakeside Cottage w/ Deck, Views

3.0 star property
Wisconsin Lakeside Cottage w/ Deck, Views
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!
Winter Vacation Rental | 7BR | 4BA | 6,700 Sq Ft | Stairs Required

Spacious Winter Retreat w/ River Access + Kayaks!

9.0 out of 10, Wonderful, (18)
"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!
Luxury Cabin, 800+ feet frontage, 733 acre Lake, Hot tub, Pontoon, Fireplace .
Property grounds

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

10.0 out of 10, Exceptional, (18)
"Couldn't have asked for a better romantic getaway!"
Luxury Cabin, 800+ feet frontage, 733 acre Lake, Hot tub, Pontoon, Fireplace .
Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin
Interior

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

Why book your cottage in Winter with Expedia?
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!
How can I find cheap cottages in Winter?
With Expedia’s filter tool, booking cheap cottages in Winter couldn’t be easier. To discover properties that’ll make your bank balance smile, refine your search results by star rating, budget and amenities.