Winter Holiday Rentals from AU$234: Search Short-Term Rentals

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

Breezy Bay Beach On Round Lake : This holiday home rental outside of Winter is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

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Holiday Rentals in Winter

Set against a serene lake, this cabin features a unique star-shaped window and a well-maintained lawn.

"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! "

Relax in this cabin-style room with a dining table, comfortable sofa, and seating areas for socializing and relaxation.

"Great cabin! Loved being by freinds . Love this campground."

Enjoy a peaceful retreat in this cabin surrounded by nature, with a porch perfect for dining and taking in the serene surroundings.

Enjoy the serene forest view from the comfort of your room, where two wicker chairs invite you to sit and take in the natural scenery.

"Perfect lodging option in a wonderful location."

includes taxes & fees

5 Aug - 6 Aug

Enjoy serene views of the water from this deck.

"Loved our stay for Birkie weekend!"

includes taxes & fees

25 Aug - 26 Aug

Relax in a cabin-style room with a large window offering a view of the surrounding trees and deck.

"Loves the location and beautiful Round Lake! Our family could all be together and relax with plenty of space!"

Enjoy meals in this cabin's spacious dining area with a large table and comfortable seating for all.

"Everything was very comfortable. It is BYOW(bring your own whisk) but thats it. Movie selection was great too"

includes taxes & fees

20 Aug - 21 Aug

Enjoy cooking in this well-equipped kitchen with a central island and bar stools.

Cozy cabin-style room with a rustic ambiance, featuring a wooden floor and walls, wicker chairs, and large windows offering forest views.

"It was an amazing stay. The lake was beautiful even frozen. Quiet, cozy, comfortable. All around relaxing and Amazing stay. Will 100% stay again."

Relax in a cozy living area with a fireplace, comfortable seating, and scenic views of the surrounding forest.

"Beautiful place to stay."

Kitchen features an oven, microwave, and sink with a window above.

"Beautiful, comfortable stay."

Enjoy meals and relaxation on the deck with a round table, bench, and dining area.

"This property was PERFECTION. Highly recommend and so grateful! "

Cozy retreat with a large bed, wooden paneling, and a window offering a view of the outdoors.

"Wonderful home and location."

Relax in Adirondack chairs by the serene lake, with a dock extending into the water for boating or fishing.

"Our large group stayed at the cabin while in town for a Men’s Hockey Tournament. The cabin was perfect for our group, good location for Stone Lake and Hayward, and easy access. There was plenty of space and the coordination of the cabin by Cassidy was great. Location was quiet, yet accessible. Would highly recommend, it was perfect for our group."

Relax in a cozy cabin-like setting with a rustic bar and comfortable seating.

"Comfortable, beautiful property!"

Cozy cabin features a high ceiling, large windows, a sofa, dining table, flat-screen TV, and a fireplace.

"This was a great property. We are hoping to retire when the weather warms. "

Enjoy meals in this well-equipped kitchen with a central island and dining area.

"Very nice property on a lake great for paddle boarding. We had a great time."

Cozy dining area with a round table and two chairs, a lamp, and a kitchen in the background.

"Beautiful place to take a family"

Cozy retreat with a comfortable seating area, TV, and decorative touches.

"Location was great; the kayaks and paddle boards were very nice. The living room furniture could use an upgrade .Overall it was a wonderful family trip!"

Enjoy cooking in this well-equipped kitchen with a central island, gas stove, oven, and microwave.

"Our group loved this property and location! Would definitely book again for both the house and the biking!!"

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Top Winter Hotel Reviews

Holiday Inn Express & Suites Hayward by IHG

10/10 Excellent

"The door to my room didn't close properly. It was sticky and required some force to close/"

Big Chip Lodge. Awesome view. Dock 50' away. Authentic Historical Wisconsin.

10/10 Excellent

"This was our second year at the chip lodge. we liked it so much the first year that we had to come back. the first year we showed up there was maybe 15 people and the house easily accommodated us. its a rustic vibe. things are old and perhaps that is the charm and what we like about it. the highlight for us is definitely the slow cruises on the pontoon boat as we explored the lake. The kitchen is huge and designed to feed a lot of people. Gary is a nice guy. He lives right next door which is helpful if you have any questions about the lake, boats, lures, fishing, and everything else. The view from the large deck is exceptional. Enjoy your stay here. I'd recommend this place for any large group."

Modern Cabin located between Grindstone and Lac Courte Oreilles

10/10 Excellent

"We loved this cabin and enjoyed our stay. The cabin was so clean and had little extras like super fluffy towels. We especially loved the screen porch. We spent so much of our time on the porch playing games, reading, and having fun. It was also pretty warm our last evening there, and the porch provided a little breeze so it wasn’t quite as warm. The only drawback in the summer is that the cabin is not air conditioned, but we knew this when we booked our stay, so we made the best of it. We would definitely book here again! "

Northwoods Motels

10/10 Excellent

"The room was comfortable/tastefully decorated. Their website stated that breakfast was provided. In checking in, I was told that they are no longer providing breakfast. The ice machine is not working but if you ask, a bag of ice will be provided. The cleanliness could be improved. I wiped a spill off from the bathroom floor and the tissue was black. There were also black areas on the edges of the shower curtain as if a mechanic with greasy hands had handled it. I wiped off a spot of dried blood from the wall where the toilet paper was hanging. The property could certainly use some TLC. I'm thankful to have been able to stay there seeing that everything in Ladysmith was booked up."

Hayward, Round Lake Retreat! Private dock, 3 kayaks, beautifully maintained!

10/10 Excellent

"We arrived mid afternoon on Saturday 7/12. Check in was seamless, code for entrance was sent the week before. Cabin was spotless up and down. Beautiful bedrooms with very comfy beds. View of the lake from the cabin and deck were perfect! Very well equipped kitchen, with tons of extras. Liz was wonderful to communicate with and very quick to respond to all questions and concerns. Very nice, sturdy dock with plenty of room for a 24' pontoon boat. Would give the cabin, and Liz more stars if possible. We have stayed at several properties on Round Lake. This was easily the nicest! We're looking forward to our next stay."

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

10/10 Excellent

"Great stay at this little gem! Very tidy and comfortable. Had a visit from a friendly doe each evening. Cabin well equipped with everything we needed. Bonsey (dog) loooved surveying his vacation kingdom from the little dock!!"

EAGLE LODGE - Cozy Cabin Overlooking the Beautiful E. Fork of the Chippewa River

10/10 Excellent

"The cabin was simple comfort for a couple and their dog, with all the necessities. The view of the river was beautiful and the fishing right out the door was great too. Excellent truck and trailer parking, with a plug in to charge the boat batteries. Great Lakes to fish within a 40 mile or less radius. We would definitely stay again!"

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$234 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.

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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?

Breezy Bay Beach On Round Lake: This holiday home rental outside of Winter is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Winter?

Choose from 13 Expedia holiday rentals in Winter for a memorable holiday.

What can I see and do in Winter?

Lake Winter and Perch Lake 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.

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Winter Holiday Rentals

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Holiday Rentals in Winter

Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

EAGLE LODGE - Cozy Cabin Overlooking the Beautiful E. Fork of the Chippewa River

EAGLE LODGE - Cozy Cabin Overlooking the Beautiful E. Fork of the Chippewa River

Vintage log cabin located in the Chequamegon National Forest on Blaisdell Lake.

Vintage log cabin located in the Chequamegon National Forest on Blaisdell Lake.

Telemark Northwoods Lodging

Telemark Northwoods Lodging

Hayward, Round Lake Retreat! Private dock, 3 kayaks, beautifully maintained!

Hayward, Round Lake Retreat! Private dock, 3 kayaks, beautifully maintained!

Round Lake Cabin Retreat

Round Lake Cabin Retreat

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

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

Victory Heights Haven – Sandy Shoreline on LCO

Victory Heights Haven – Sandy Shoreline on LCO

Moose Lake Hayward WI

Moose Lake Hayward WI

Breezy Bay Beach On Round Lake

Breezy Bay Beach On Round Lake

Phillips Cabin w/ Lake Views & Private Dock!

Phillips Cabin w/ Lake Views & Private Dock!

Modern Cabin located between Grindstone and Lac Courte Oreilles

Modern Cabin located between Grindstone and Lac Courte Oreilles

Exclusive Home On Chippewa Flowage- 3.6 acres with sand beach and two Private docks

Exclusive Home On Chippewa Flowage- 3.6 acres with sand beach and two Private docks

Northwoods multiple family size cabin. ATV/UTV, snowmobile trail access and lake

Northwoods multiple family size cabin. ATV/UTV, snowmobile trail access and lake

Executive Custom Log Lodge on Little Round Lake

Executive Custom Log Lodge on Little Round Lake

Lakefront Wisconsin Cabin with Boat Dock!

Lakefront Wisconsin Cabin with Boat Dock!

Lake Hayward. Private Lakefront Within Walking Distance To Downtown Hayward

Lake Hayward. Private Lakefront Within Walking Distance To Downtown Hayward

" The Cabernet Cabin"

" The Cabernet Cabin"

Round Lake Hideaway

Round Lake Hideaway

Beautiful Craftsman Style Lake Home

Beautiful Craftsman Style Lake Home

Top Winter Hotel Reviews

Holiday Inn Express & Suites Hayward by IHG

Find out more about Winter

Find out more about Winter

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