Find a Bed and Breakfast in Winter from CA $63

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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10
No exact matches found, but these alternatives could be just right

Recommended hotels in Winter

A spacious lobby with a large window overlooking a lake, furnished with leather sofas and wooden tables, and featuring rustic decor including antler wall art.

1. Holiday Inn Express & Suites Hayward by IHG

Holiday Inn Express & Suites Hayward by IHG
2.5 star property
Hayward
9.6 out of 10, Exceptional, (730 reviews)
"From check in to check out the place was clean, beautiful room and delicious breakfast especially loved the cinnamon rolls and the fresh coffee"
United States
Cynthia
The price is CA $196
CA $215 total
includes taxes & fees
Nov 29 - Nov 30
Holiday Inn Express & Suites Hayward by IHG
A hotel room with a large bed, a TV, a desk, a bathtub, and a window with a view of greenery.

2. AmericInn by Wyndham Ladysmith

AmericInn by Wyndham Ladysmith
3.0 star property
Ladysmith
8.2 out of 10, Very good, (133 reviews)
"Clean room, friendly staff "
United States
marcus
The price is CA $148
CA $165 total
includes taxes & fees
Nov 29 - Nov 30
AmericInn by Wyndham Ladysmith
A view through a window of a grassy yard with a lake, trees, and a small building.

3. 2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage

2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
Hayward
9.2 out of 10, Wonderful, (26 reviews)
"We liked the property and the cabin was fine. Management was not available and there was no communication. The grounds were in need of up keep. The weather was tremendous. All in all we had a good stay because we are simple folks that know how to enjoy ourselves."
United States
Dawn
The price is CA $141
CA $169 total
includes taxes & fees
Nov 12 - Nov 13
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
A dining area with multiple tables and chairs, a door with an exit sign, and a window with a view of the outside.

4. Super 8 by Wyndham Phillips

Super 8 by Wyndham Phillips
2.0 star property
Phillips
8.2 out of 10, Very good, (294 reviews)
"Always a great friendly staff and wonderful stay"
United States
Danny
The price is CA $119
CA $130 total
includes taxes & fees
Nov 18 - Nov 19
Super 8 by Wyndham Phillips
A tray with breakfast items including eggs, bacon, and a muffin, a glass of orange juice, and a hot tub in the background.

5. Secluded Riverfront Cabin | Hot Tub + Starlink

Secluded Riverfront Cabin | Hot Tub + Starlink
Ojibwa
10.0 out of 10, Exceptional, (50 reviews)
"We had such a good time! "
United States
Dan P.
The price is CA $637
CA $768 total
includes taxes & fees
Nov 18 - Nov 19
Secluded Riverfront Cabin | Hot Tub + Starlink
A hotel room with a large bed, two bedside tables, a chair, a wall-mounted air conditioner, and a framed picture.

6. AmeriVu Inn

AmeriVu Inn
2.0 star property
Park Falls
8.0 out of 10, Very good, (410 reviews)
"They could have a better breakfast."
United States
Joseph
The price is CA $126
CA $139 total
includes taxes & fees
Dec 12 - Dec 13
AmeriVu Inn
A modern kitchen with wooden cabinets, a built-in coffee machine, and a flat-screen TV.

7. Northern Lights Inn

Northern Lights Inn
2.5 star property
Park Falls
7.8 out of 10, Good, (240 reviews)
"Owner was friendly and would stay there again."
United States
Mattison
The price is CA $130
CA $143 total
includes taxes & fees
Nov 12 - Nov 13
Northern Lights Inn
An indoor swimming pool with wooden beams, clear water, and a 30 ft depth marker.

8. Quality Inn Ladysmith

Quality Inn Ladysmith
2.5 star property
Ladysmith
8.8 out of 10, Excellent, (300 reviews)
"I like the large pool and jacuzzi."
United States
Brenda
The price is CA $155
CA $173 total
includes taxes & fees
Dec 1 - Dec 2
Quality Inn Ladysmith
A bedroom with a wooden sloped ceiling, a bed with a patterned bedspread, two bedside tables with lamps, and three framed pictures on the wall.

9. Timber Inn

Timber Inn
2.0 star property
Phillips
7.0 out of 10, Good, (338 reviews)
"My family and I had a wonderful stay at the Timber Inn! It is clear that the new owners are putting a lot of time and care into the space. The rooms were clean and comfortable, the amenities were thoughtful, and the staff extremely helpful. Would definitely stay here again when we're in the area!"
United States
Kelsey
The price is CA $89
CA $97 total
includes taxes & fees
Nov 12 - Nov 13
Timber Inn
A wooden deck with two wicker chairs and a table, overlooking a forest with autumn foliage.

10. Telemark Northwoods Lodging

Telemark Northwoods Lodging
3.5 star property
Cable
9.0 out of 10, Wonderful, (331 reviews)
"Clean, quiet…easy check in. Great communication pre check-in. Beautiful setting/area. Will be back…"
United States
Thomas
The price is CA $127
CA $139 total
includes taxes & fees
Nov 12 - Nov 13
Telemark Northwoods Lodging
Reception

11. Northwoods Motels

Northwoods Motels
2.5 star property
Ladysmith
6.6 out of 10, (153 reviews)
"Great stay!"
United States
Gregory
The price is CA $140
CA $147 total
includes taxes & fees
Nov 12 - Nov 13
Northwoods Motels
An outdoor seating area with Adirondack chairs and a fire pit, surrounded by a forested landscape.

12. Kavanagh Bay Resort|Hot Tub&Sauna #1

Kavanagh Bay Resort|Hot Tub&Sauna #1
Hayward
7.2 out of 10, Good, (5 reviews)
"This host was amazing! The house was clean and exactly what we were looking for. The hot tub was warm and an awesome way to relax after a long day of snowmobiling. We definitely look forward to staying here again!!"
United States
Chelsie H.
The price is CA $235
CA $778 total
includes taxes & fees
Nov 12 - Nov 13
Kavanagh Bay Resort|Hot Tub&Sauna #1
A view through a window of a grassy yard with a pond, trees, and a small building.

13. 2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage

2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
Hayward
8.4 out of 10, Very good, (11 reviews)
"Cabin was perfect for our needs. Host met us and let us know the important information about the property and let us be. Would stay again."
United States
Katie L.
The price is CA $141
CA $169 total
includes taxes & fees
Nov 12 - Nov 13
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
A cozy room with a bed, a sofa, a wooden wall, a door, and a small table with a lamp.

14. Chip-Wa Lodging Room 1

Chip-Wa Lodging Room 1
Hunter
10.0 out of 10, Exceptional, (3 reviews)
"Enjoyed our stay. Cozy and quaint."
United States
Thane B.
The price is CA $162
CA $207 total
includes taxes & fees
Nov 12 - Nov 13
Chip-Wa Lodging Room 1
A wooden cabin with a porch, surrounded by trees with autumn foliage.

15. Lake Cabin · Hot Tub · Fire Pit · Free Firewood

Lake Cabin · Hot Tub · Fire Pit · Free Firewood
Hayward
9.8 out of 10, Exceptional, (25 reviews)
"the place is in good shape and the location is awesome. "
United States
Kevin R.
The price is CA $417
CA $1,044 total
includes taxes & fees
Nov 12 - Nov 13
Lake Cabin · Hot Tub · Fire Pit · Free Firewood
A spacious living area with a wooden floor, a sofa, a coffee table, and a kitchen area with a large window.

16. Renovated cabin on Lac Courte Oreilles Lake - minutes from trails!

Renovated cabin on Lac Courte Oreilles Lake - minutes from trails!
Northwoods Beach
10.0 out of 10, Exceptional, (26 reviews)
"Our second time staying and we love it! We especially enjoyed the addition of the front/lake facing deck "
United States
ANN M.
The price is CA $267
CA $471 total
includes taxes & fees
Nov 12 - Nov 13
Renovated cabin on Lac Courte Oreilles Lake - minutes from trails!
A campsite with a trailer, a tent, and a car.

17. Rustic campground in Butternut

Rustic campground in Butternut
Butternut
The price is CA $64
CA $85 total
includes taxes & fees
Nov 12 - Nov 13
Rustic campground in Butternut
A gravel driveway leading to a small, single-story building surrounded by dense trees and greenery.

18. Comfortable 3 Bedroom Cabin On the Shores of Lake Chippewa Flowage in Hayward WI

Comfortable 3 Bedroom Cabin On the Shores of Lake Chippewa Flowage in Hayward WI
Hayward
9.2 out of 10, Wonderful, (10 reviews)
"We felt like we we transported to the 60’s. The atmosphere and ambiance fit. We had everything we needed and the management was great. If you want old school WI resort this is your place!"
United States
Nina H.
The price is CA $282
CA $352 total
includes taxes & fees
Nov 18 - Nov 19
Comfortable 3 Bedroom Cabin On the Shores of Lake Chippewa Flowage in Hayward WI
A rustic cabin surrounded by dense forest.

19. 2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage

2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
Hayward
8.4 out of 10, Very good, (20 reviews)
"Thank you for the great stay! I had everything I needed."
United States
Mark B.
The price is CA $176
CA $221 total
includes taxes & fees
Nov 18 - Nov 19
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
Interior

20. Ultimate Hayward Trailhead Cabin

Ultimate Hayward Trailhead Cabin
Hayward
10.0 out of 10, Exceptional, (1 review)
"My husband and I had a wonderful stay at this cabin. The pictures and description are totally accurate. The home was clean, well furnished and as comfortable as home including the beds. The kitchen was well equipped with everything we needed and the linnens were fresh, new and plush. The shower is spacious and there was plenty of hot water. The screened porch was wonderful to sit out in the afternoon and watch the leaves fall in the breeze. (We were there early October). We found lots of...
United States
Joan O.
The price is CA $211
CA $386 total
includes taxes & fees
Nov 12 - Nov 13
Ultimate Hayward Trailhead Cabin
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.
View all properties

Learn more about Winter

Snowmobilers and ice fishers flock to Winter's frozen lakes, where the Tuscobia State Trail offers prime access for winter sports enthusiasts. Warm up at the Winter Greenhouse with its tropical plants, then ask locals about nearby Flambeau River State Forest for summer kayaking adventures.

See all hotels in Winter
A snowy landscape with a red barn and a red shed.

Top reviews in Winter

A spacious lobby with a large window overlooking a lake, furnished with leather sofas and wooden tables, and featuring rustic decor including antler wall art.
Holiday Inn Express & Suites Hayward by IHG

Holiday Inn Express & Suites Hayward by IHG

Holiday Inn Express & Suites Hayward by IHG
Hayward

10/10 Excellent

Highly recommend.
Canada
Harkiran
Reviewed September 16, 2025
Holiday Inn Express & Suites Hayward by IHG

Frequently Asked Questions

Searching for B&Bs in Winter?

If you want to find an accommodation with a small number of rooms and a cozy environment, a bed and breakfast may be the perfect thing for your trip to Winter. If you're interested in playing some golf on your trip, Barker Lake Golf Course is a good spot to tee off.

Are you thinking about a B&B instead of a traditional hotel?

With attentive service, opportunities to mingle with other guests, and delectable breakfasts, B&Bs offer a truly one-of-a-kind environment.

When should I stay at a B&B in Winter?

When you're dreaming of a trip to Winter, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 64°F, while the coldest months are January and February with an average of 18°F. The snowiest months in Winter are April, March, January, and February, with each month seeing an average of 10 inches of snowfall.

What is there to do in Winter?

When you want to spend some time in the great outdoors, Lake Winter and Barker Lake are some notable spots. You might put Lake Chippewa and Chequamegon National Forest on your list if you want to see more of the area.

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