Search Winter hotels

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check Winter hotel prices

Tomorrow night
This weekend

Filter by

Guest rating
Guest rating
Property class

Top hotels and accommodation in Winter

Cobblestone Bed and Breakfast
3.0 star property
10.0 out of 10, Exceptional, (5)
"The owner was was very kind, friendly, and accommodating and had a cute gift shop. She also made a wonderful breakfast that started out with a baked apple! The yard and house were decorated very nicely for the holidays, complete with music to add to the ambiance. The room had everything we needed and included an amazing copper bath tub that was wonderful to soak in. Overall it was a great place to sleep and relax with much more character than a hotel room could ever have. "
The price is AU$301
includes taxes & fees
27 Nov - 28 Nov
Cobblestone Bed and Breakfast
Cozy Birchwood Retreat on UTV Trail w/ Hot Tub!
9.0 out of 10, Wonderful, (16)
"Good "
Cozy Birchwood Retreat on UTV Trail w/ Hot Tub!
Relax in our French Quarters Room at The Cobblestone Bed & Breakfast
10.0 out of 10, Exceptional, (1)
"Very interesting collection of furnishings and miscelania, lots of character (including hostess), terrific breakfast."
The price is AU$282
includes taxes & fees
29 Nov - 30 Nov
Relax in our French Quarters Room at The Cobblestone Bed & Breakfast
Charming 2-bedroom house located in Ojibwa WI just off the Tuscobia Trail.
2.0 star property
The price is AU$328
includes taxes & fees
24 Nov - 25 Nov
Charming 2-bedroom house located in Ojibwa WI just off the Tuscobia Trail.
Lakefront Efficiency Condo, Indoor Pool/Hot Tub-Tagalong Golf Resort Unit431B
10.0 out of 10, Exceptional, (30)
"We loved it - the condo was perfect. We went ATVing and the trails are very convenient to this area. The condo was extremely clean, comfortable and had everything we needed. I will definitely stay there again. Location was fantastic."
Lakefront Efficiency Condo, Indoor Pool/Hot Tub-Tagalong Golf Resort Unit431B
Lakeside cabin! Great fishing, on the ATV trail
8.4 out of 10, Very good, (5)
"We loved the location and serenity of your property. The yard could be cleaned up and interior was ok but not fancy. "
The price is AU$390
includes taxes & fees
24 Nov - 25 Nov
Lakeside cabin! Great fishing, on the ATV trail
Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin
8.8 out of 10, Excellent, (16)
"Newer owner is showing improvement to property."
Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin
Cozy Birchwood Condo on Tagalong Golf Course!
3.0 star property
Cozy Birchwood Condo on Tagalong Golf Course!
Bucktail Lodge Lakeview Cabin on Barker Lake in Winter, Wisconsin
8.0 out of 10, Very good, (3)
"Loved our stay at Bucktail Lodge! So beautiful. "
Bucktail Lodge Lakeview Cabin on Barker Lake in Winter, Wisconsin
Cozy Birchwood Condo on Tagalong Golf Course!
9.2 out of 10, Wonderful, (5)
"Beautiful property. Quiet, as golfing/boating/fishing seasons are over. (Too cold/rainy). Property is awesome for a winter conference or retreat. Views are amazing. Wade"
Cozy Birchwood Condo on Tagalong Golf Course!
Unit 312 1 BD/ 1 BA Condo
3.0 star property
10.0 out of 10, Exceptional, (1)
The price is AU$265
includes taxes & fees
15 Dec - 16 Dec
Unit 312 1 BD/ 1 BA Condo
Bill's Hideout
10.0 out of 10, Exceptional, (4)
"Was in town for a family gathering and only needed one night’s stay. The host was very accommodating. My family members and I were very satisfied with the property. Too bad we were only there for one night, we definitely would have liked to spend more time. Will keep this property in mind for next time in town to visit our family. "
The price is AU$462
includes taxes & fees
17 Dec - 18 Dec
Bill's Hideout
Relax in our English Garden King Suite at The Cobblestone Bed & Breakfast
2.0 star property
10.0 out of 10, Exceptional, (1)
"Breakfast was amazing. The owner was so kind, friendly and professional. We would gladly book this place again."
The price is AU$415
includes taxes & fees
29 Nov - 30 Nov
Relax in our English Garden King Suite at The Cobblestone Bed & Breakfast
Bucktail Lodge Pineview cabin on Winter, Wisconsin.
7.0 out of 10, Good, (4)
"The cabins are conveniently located by the water and well-maintained. The staff is welcoming, and the overall ambiance is laid-back. It's worth noting that the cabins, bar, and outbuildings are closely situated on the property. If you're seeking seclusion or a sense of being surrounded by wilderness, this might not be the ideal choice. However, the property is indeed surrounded by wilderness and offers a peaceful retreat far from city life."
Bucktail Lodge Pineview cabin on Winter, Wisconsin.
Relax in our Parlor Room at The Cobblestone Bed & Breakfast
The price is AU$280
includes taxes & fees
23 Nov - 24 Nov
Relax in our Parlor Room at The Cobblestone Bed & Breakfast
ATV riders! Private wooded lot, cottage access to trails! Dogs! Firepit!
10.0 out of 10, Exceptional, (22)
"We had a great trip. We put on 300 plus miles Got to see a bear and a wolf and and a bunch of turkeys and deer while out riding The cabin is set up very well plenty of room will look at staying there again in the future Thanks "
ATV riders! Private wooded lot, cottage access to trails! Dogs! Firepit!
Luxury Cabin, 800+ feet frontage, 733 acre Lake, Hot tub, Pontoon, Fireplace .
10.0 out of 10, Exceptional, (14)
"My husband and I stayed for a long weekend and the place is absolutely gorgeous, inside and out. Its by far the cleanest rental we've stayed at, eket you'd expect at a nice hotel. Beautiful fall colors enjoyed while kayaking and stargazing all night!"
Luxury Cabin, 800+ feet frontage, 733 acre Lake, Hot tub, Pontoon, Fireplace .
Relax in our Bear's Den Room in the Lower Lodge at The Cobblestone Bed & Breakfast
The price is AU$282
includes taxes & fees
29 Nov - 30 Nov
Relax in our Bear's Den Room in the Lower Lodge at The Cobblestone Bed & Breakfast
Unit 411a 1 BD/ 1 BA Condo
3.0 star property
10.0 out of 10, Exceptional, (3)
"Love the location. It is a large and beautiful condo. "
The price is AU$265
includes taxes & fees
15 Dec - 16 Dec
Unit 411a 1 BD/ 1 BA Condo
EAGLE LODGE - Cozy Cabin Overlooking the Beautiful E. Fork of the Chippewa River
9.8 out of 10, Exceptional, (10)
"Cabin was impeccable as always. Beautiful river front views. Pet friendly. "
EAGLE LODGE - Cozy Cabin Overlooking the Beautiful E. Fork of the Chippewa River
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.
Don't see what you're looking for?
See all available properties in Winter
Save an average of 15% on thousands of hotels when you're signed in
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

What's the best place to stay in Winter?

Cobblestone Hotels & Suites – Ladysmith, located 25.4 mi (41 km) from the heart of Winter, is a top choice for your stay, based on our traveller data. Two other choices for your trip to the area are Holiday Inn Express & Suites Hayward, an IHG Hotel and Telemark Northwoods Lodging. See all available top hotels, or vacation rentals in Winter.

What are some of the best holiday rentals that Winter has to offer?

Spacious Winter Retreat w/ River Access + Kayaks!: This highly rated holiday home rental in Winter offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. Another good choice for your trip to Winter is Bears Den on the private lake. See all vacation rentals in Winter.

If I need to cancel my hotel reservation in Winter, will I receive a refund?

Yes! Most room reservations are refundable if you cancel before the hotel’s cancellation deadline, which is often 24 or 48 hours before your check-in date. If you have a non-refundable reservation, you might still have the option to cancel and receive a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Winter.

What's the best accommodation option for a family trip to Winter?

"Upscale Accommodations" with an "Up North" location! is a resort with in-room kitchens and free WiFi, and it's a top choice on Expedia for families. Other good choices to stay with the children include Historic prohibition Lodge next to golf course with private beach and "Upscale Accommodations" with an "Up North" location! . Find more child-friendly accommodations in Winter.

What are some accommodation options with pools in Winter?

Cobblestone Hotels & Suites – Ladysmith: Features daily, an indoor pool and free self parking. Holiday Inn Express & Suites Hayward, an IHG Hotel and AmericInn by Wyndham Ladysmith are two additional hotels that feature an on-site pool. View all hotels with pools in Winter.

What's it like staying in Winter?

Those travelling to Winter will definitely enjoy the sights to see and things to do. In Winter, there are 51 hotels and other accommodation options to choose from. Find out more about Winter.

What should I see while I'm in Winter?

Natural beauty is on display at Lake Winter, Ojibwa State Park and Barber Lake. A couple of additional sights to add to your itinerary are Black Dan Lake and Fishtrap Lake. Take a look at what more there is to see and do in Expedia's Winter guide.

What's the seasonal weather like in Winter?

The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -8°C. The snowiest months in Winter are April, March, January and February, with each month seeing an average of 26 cm of snowfall.