Winter Vacation Rentals from ￥16,085: Search Short-Term Rentals

Q: What's the top vacation rental in Winter?

Bears Den on the private lake : This Winter vacation home rental is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

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Vacation 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."

￥22,344 total

includes taxes & fees

Aug 10 - Aug 11

Enjoy serene views of the water from this deck.

"Loved our stay for Birkie weekend!"

￥87,098 total

includes taxes & fees

Aug 25 - Aug 26

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"

￥45,928 total

includes taxes & fees

Aug 20 - Aug 21

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.

"Our first time staying here. Perfect cabin for our weekend of fishing. Wish we had booked a couple more days. Walleye fishing was excellent. We will be back."

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

"Beautiful place to 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!!"

Relax in a warm, inviting space with a central sofa, matching armchair, and large mirror.

"My partner and I stayed there for 3 nights in the middle of April. The cabin was very cozy, and the location was in the middle of a little bit of everything. Our favorite things were the screened in porch and the convince of the canoe. "

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Top Winter Hotel Reviews

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

10/10 Excellent

"This property is amazing, well appointed, good location, very clean, excellent sandy beach and a top-notch host. The host was helpful, engaged, and responsive. We intend to be back in the near future. "

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."

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

Search for holiday rentals in Winter on Expedia! You can easily find your home rentals, villas, holiday apartments in Winter using one of the methods below:

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Look no further and take a look at our great range of rental properties in Winter!

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All accommodation types in Winter

Frequently asked questions

Can I find a vacation rental in Winter?

Yes, you can find vacation rentals near top attractions in Winter, or you can choose a more secluded option if you're looking for relaxation.

What's the top vacation rental in Winter?

Bears Den on the private lake: This Winter vacation home rental is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Winter?

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

What can I see and do in Winter?

Lake Winter and Bluegill 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 vacation rentals like in Winter?

Vacation rentals are privately owned accommodations you can stay in for several days or longer in Winter. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll have a home away from home. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for a small group gathering.

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Winter Vacation Rentals

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Vacation Rentals in Winter

Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

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.

Telemark Northwoods Lodging

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

Round Lake Cabin Retreat

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

Victory Heights Haven – Sandy Shoreline on LCO

Moose Lake Hayward WI

Breezy Bay Beach On Round Lake

Modern Cabin located between Grindstone and Lac Courte Oreilles

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

Executive Custom Log Lodge on Little Round Lake

Lakefront Wisconsin Cabin with Boat Dock!

Lake Hayward. Private Lakefront Within Walking Distance To Downtown Hayward

" The Cabernet Cabin"

Round Lake Hideaway

Beautiful Craftsman Style Lake Home

The fishing is great! Trails are close by. Enjoy summer in the Northwoods!

Top Winter Hotel Reviews

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

Holiday Inn Express & Suites Hayward by IHG

AmeriVu Inn

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

Modern Cabin located between Grindstone and Lac Courte Oreilles

Round Lake Cabin Retreat

Northwoods Motels

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

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

Find out more about Winter

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Frequently asked questions