Winter Holiday Rentals from AU$374: Search Short-Term Rentals

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Our top choices for Winter holiday rentals

1. Secluded Riverfront Cabin | Hot Tub + Starlink

Ojibwa

Dan P.

includes taxes & fees

30 Sept - 1 Oct

A view through a window of a grassy yard with a pond, trees, and a small building.

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

Hayward

Katie L.

includes taxes & fees

8 Oct - 9 Oct

A room with two beds, a desk, a chair, and a window.

3. Chip-Wa Lodging Room 4

Hunter

Charles

includes taxes & fees

8 Oct - 9 Oct

A spacious living area with a wooden floor, a sofa, a coffee table, and a kitchen area with a large window.

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

Northwoods Beach

ANN M.

An outdoor seating area with Adirondack chairs and a fire pit, surrounded by a forested landscape.

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

Hayward

Chelsie H.

includes taxes & fees

27 Sept - 28 Sept

A cozy log cabin interior with a wooden ceiling, a ceiling fan, a large arched window, a leather sofa, a coffee table, and a small side table.

6. Lakefront Cabin on LCO - The Sunset Escape

Hayward

Jeffrey T.

includes taxes & fees

28 Sept - 29 Sept

A wooden deck with two wicker chairs and a table, overlooking a forest with autumn foliage.

7. Telemark Northwoods Lodging

Cable

Adam

includes taxes & fees

22 Oct - 23 Oct

A wooden cabin interior with a large dining table, chairs, and a view of a lake through large windows.

8. Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!

Hayward

Eric Z.

includes taxes & fees

28 Sept - 29 Sept

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Top Winter Hotel Reviews

Timber Inn

8/10 Good

"New owners have remarkable turn things around looking pretty good after a lot of clean up"

AmericInn by Wyndham Ladysmith

8/10 Good

"The hotel is older, but in good condition and clean. The staff were helpful. I would probably have stayed again, but the day I left, my credit card was hacked. I was in Ladysmith for a few days before I checked out and had no issues when I used the credit card at other places, but the day I checked out, I was hacked and had to get a new card. Since I've not stayed there before and have not had this happen before, I may consider it a coincidence."

Quality Inn Ladysmith

10/10 Excellent

"Everything was just so cozy from the front office decor to the bed and bedding itself and the lighting by the bed when I walked into the room. The shower was relaxing and all amenities were available which was convenient that I didnt need to bring an iron with me and was able to make my first cup of coffee in the morning. The airiconditioning was nice and cool. The room was spacious. I watched a little TV before bed. I slept so very comfortably until my morning alarm! Easy and quick check out and super nice staff! I highly recommend staying here!"

Charming 2-bedroom Hayward Cabin on Lac Courte Oreilles

10/10 Excellent

"Just a little fishing trip by myself. Very relaxing, fish didn’t cooperate but that’s fishing. If I’m still around next year I’ll be staying again. Brandon was very helpful when I couldn’t get the keurig machine to work, but there was another that he told me where it was, so had my coffee in the mornings. Everything else was fine."

Find out more about Winter

Everything you need to know about Winter holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winter holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winter holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Winter holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winter. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winter holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winter holiday rentals we have selected for you start as low as AU$374 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winter rentals

At Expedia, we put the best Winter holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winter rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winter holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winter. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a holiday rental in Winter?

Yes, there are holiday rentals close to the most popular sights in Winter, or you can select a more secluded option if you're looking for a relaxing stay.

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

5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.: This highly rated holiday home rental in Winter is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 6 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. Our travellers also rate Amazing Sunsets, Peaceful, Well Maintained Lake home on Beautiful, Barker lake as a favourite home for rent in Winter.

How many holiday rentals are there in Winter?

Choose from 12 Expedia holiday rentals in Winter for a memorable holiday.

What can I see and do in Winter?

Lake Winter and Lake Chippewa are a couple of lovely local spots to get outside and enjoy nature. Chequamegon National Forest and Flambeau River are other places to visit while you're in town.

What are holiday rentals like in Winter?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winter. Holiday rentals feature extras like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for a small group gathering.

Winter Holiday Rentals

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Treat yourself

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Check prices for these dates

Our top choices for Winter holiday rentals

1. Secluded Riverfront Cabin | Hot Tub + Starlink

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

3. Chip-Wa Lodging Room 4

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

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

6. Lakefront Cabin on LCO - The Sunset Escape

7. Telemark Northwoods Lodging

8. Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!

9. 2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage

10. Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails.

11. Lake Front Cabin, Media/Game Room, Kayaks, Multi-level deck--NEWLY REMODELED

12. Ultimate Hayward Trailhead Cabin

13. Chip-Wa Lodging Room 6

14. Chip-Wa Lodging Room 5

15. Blissful cozy, year round, lakeside cabin on Butternut Lake. Dogs welcome.

16. Chip-Wa Lodging Room 1

17. 15min to trailhead, King Bed, PacMan

18. The Blue Musky Golf, UTV & Snowmobile Escape

19. Lakefront cottage w/ convenient access to restaurants, atv and snowmobile trails

20. Chip-Wa Lodging Room 2

Find holiday rentals that suit your style

Top Winter Hotel Reviews

Timber Inn

Find out more about Winter

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