Winter Holiday Rentals from NZ$267: Search Short-Term Rentals

Q: 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. Our travellers also rate Bears Den on the private lake as a favourite home for rent in Winter.

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Holiday Rentals in Winter

TV, fireplace, DVD player, table football

"This has been the second year we’ve been here. It’s a great place for a large group with plenty of space for everyone! This will continue to be our go to spot for years to come! "

"The lake was great and the living situation for our large group was very comfortable. The only reason I give it 4 stars is because there was no hot water. The showers were absolutely freezing. Besides that everything was great."

"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! "

Deluxe Suite, 1 Bedroom, Kitchen | Terrace/patio

"Excellent property for a ski weekend! "

includes taxes & fees

4 Feb - 5 Feb

"I and a friend had a lovely writers' retreat on this lakeside cabin with a beautiful view and a fireplace. The host responded quickly to our questions, and we felt as comfortable as if we were at home. A beautiful view from the porch and within easy driving distance from the Twin Cities. "

"We stayed here on a bitterly cold weekend in January, and this cozy cabin was perfect for a weekend getaway for my family of four. Despite the cold, we enjoyed skiing on the neighborhood trails just out the cabin door. We warmed up quickly in front of the gas stove afterwards. Will definitely keep this cabin on our list of places to go back to. "

includes taxes & fees

22 Feb - 23 Feb

"We had a lovely and cozy stay! The backyard was just amazing and peaceful...had everything we could want. Only downfall was the mattresses in the bunkroom....very uncomfortable and one of the beds broke. Otherwise, a super place!"

"2nd time at this property, and love how well appointed, stocked and furnished it is. There hasn’t been a single thing I needed in the kitchen that wasn’t available. Comfortable beds, cozy and clean. "

"Loved the properties, lots of space indoors and outdoors.Wildlife prints on and around the properties. Daughter seen a black bear cub, on and around the property . So we were caution and enjoyed are stay."

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

"We had a perfect weekend staying at the cabin. Collin was really helpful. Checking in was a breeze and the cabin is well equipped with everything you could want. The cabin is located at the end of a pennisula, which makes it very private and the perfect place for some time in the North Woods!"

"First night we got there they had all the lights on for us and the fireplace going! Welcomed us with a wine basket and chocolates! Very clean and great location! We will definitely book a trip with them again! "

"We had a wonderful time at the Cattail Cabin! The fireplace was toasty, the outdoor walks were relaxing, the cabin was very clean and we all LOVED the games. Brad was very communicative so we felt we could reach out if we needed anything at all. But, everything went so smoothly that we really didn't need anything. Thanks for the wonderful stay!"

"This was a lovely stay in a beautiful area. The home was very clean, the beds & pillows comfortable. The kitchen was extremely well-stocked with pans, utensils, flatware -- for someone who loves to cook, there was plenty of equipment to produce great meals. The home is located down a long tree-lined driveway, and have the feeling of being alone, even though it's a busy, well-populated area. My husband enjoyed playing horseshoes in the yard every night. There is a nice pier over the water,...

"Excellent lake front property with excellent views! The small bunk bed room has comfortable beds for adults! Well stocked kitchen with grill tools and fire starter. 70-80’s decor but if it was modern they probably wouldn’t allow pets. I have traveled the world and really enjoyed my time here with family and friends. Good fire pit too"

"no tv,one in basement nothing to hook up to.On crappy days and nights would of been useful'."

"We booked this for a little family week getaway, it checked all of our boxes. Close to water, secluded, cozy, the hot tub, and enough space for all of us! The hosts are amazing and very communicative before and during your stay if you have any questions or feedback! We brought a couple extra kayaks, and used the ones on the property. There is a launch just up the road that gives you about 30 minutes, and another just a bit further that was just over an hour. The fire pit near the water was...

includes taxes & fees

4 Feb - 5 Feb

"Our group of five Seniors had a wonderful time. We rented both the cabin and the bunkhouse, so that we would have more space. The deck is a great area to socialize, dine, and enjoy the views. We sat on the dock and watched an Eagle “go fishing” for its breakfast. There are basic model kayaks and a canoe. We enjoyed the short drive to nearby hiking trails and Hayward. Patrick, the host, is very quick to respond to phone calls and messages. "

"This was our second time staying here and we will be back! Such an accommodating cabin. The views of the lake are beautiful, so serene and quiet.It’s immaculately, clean and stashed with anything we could possibly need. There are drawers with board games.The sunroom is a perfect spot to play games and read as a family. The basement ping pong table and dart board are an added bonus. Greta is a wonderful host and we can’t wait to be back!"

"This was a nice location with a great view "

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Other types of properties in Winter you may be interested in

"This has been the second year we’ve been here. It’s a great place for a large group with plenty of space for everyone! This will continue to be our go to spot for years to come! "

"The lake was great and the living situation for our large group was very comfortable. The only reason I give it 4 stars is because there was no hot water. The showers were absolutely freezing. Besides that everything was great."

"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! "

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 favorite 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 depends 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 NZ$267 per night. Entering your travel dates in the search wizard you might find 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.

Recent reviews of Winter properties

Newly Built Trailside Chalet in The Brook - direct access to CAMBA/Birkie Trails

5/5 Excellent

Cozy cabin getaway

"We stayed here on a bitterly cold weekend in January, and this cozy cabin was perfect for a weekend getaway for my family of four. Despite the cold, we enjoyed skiing on the neighborhood trails just out the cabin door. We warmed up quickly in front of the gas stove afterwards. Will definitely keep this cabin on our list of places to go back to. "

A verified traveller from Madison, WI stayed at Newly Built Trailside Chalet in The Brook - direct access to CAMBA/Birkie Trails

Posted 2 days ago

5/5 Excellent

"We had late check in due to family issues and they called us direct to check on us and make sure we could get keys late. CLEAN and tidy, well appointed room. We did not love the driveway as it snowed and was slippery but that was not their fault that it snowed unexpectedly. "

A verified traveller stayed at Telemark Northwoods Lodging

Posted 5 days ago

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

5/5 Excellent

Charming cabin on quiet lake

"I and a friend had a lovely writers' retreat on this lakeside cabin with a beautiful view and a fireplace. The host responded quickly to our questions, and we felt as comfortable as if we were at home. A beautiful view from the porch and within easy driving distance from the Twin Cities. "

A verified traveller stayed at Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!

Posted 2 weeks ago

Lake Hayward. Private Lakefront Within Walking Distance To Downtown Hayward

5/5 Excellent

Beautiful, comfortable, clean northwoods vacation

"This was a lovely stay in a beautiful area. The home was very clean, the beds & pillows comfortable. The kitchen was extremely well-stocked with pans, utensils, flatware -- for someone who loves to cook, there was plenty of equipment to produce great meals. The home is located down a long tree-lined driveway, and have the feeling of being alone, even though it's a busy, well-populated area. My husband enjoyed playing horseshoes in the yard every night. There is a nice pier over the water, with a 90 turn at the end, and an attached bench for 2. We spent every evening in the back yard, and sitting on the pier. The house is probably 50-60 yrs old, well-built, and appeared to have had some updating in the bathroom. The master bedroom has a whole wall of built-in wooden drawers that's just beautiful. There are lots of big windows looking out over the lake, and a nice huge pass-through counter between the kitchen & living room that allows a good view of the lake from the large kitchen, even though it's on the opposite side of the house. The owners/managers responded to email/text within a couple of hours -- we had several questions about the area. A bonus was that they could recommend several good old-fashioned Wisconsin Supper Clubs that we certainly enjoyed. Even though it's taken me 3 months to submit a review, this was a totally lovely stay, and I wanted to give appropriate "raves" about this property. We would certainly like to stay again!"

A verified traveller stayed at Lake Hayward. Private Lakefront Within Walking Distance To Downtown Hayward

Posted 3 weeks ago

Pet-Friendly Lakeside Cabin with Kayaks and Canoe!

5/5 Excellent

Wonderful Stay

"We had a wonderful time at the Cattail Cabin! The fireplace was toasty, the outdoor walks were relaxing, the cabin was very clean and we all LOVED the games. Brad was very communicative so we felt we could reach out if we needed anything at all. But, everything went so smoothly that we really didn't need anything. Thanks for the wonderful stay!"

A verified traveller from Fridley, MN stayed at Pet-Friendly Lakeside Cabin with Kayaks and Canoe!

Posted 2 months ago

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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?

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. Our travellers also rate Bears Den on the private 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 Perch Lake are a couple of lovely local spots to get outside and enjoy nature. Fishtrap Lake and Chequamegon National Forest 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

Plan, book, stay with confidence

Check prices for these dates

Holiday Rentals in Winter

Spacious Winter Retreat w/ River Access + Kayaks!

Spacious Winter Retreat w/ River Access + Kayaks!

Bears Den on the private lake

Bears Den on the private lake

Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

Telemark Northwoods Lodging

Telemark Northwoods Lodging

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

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

Newly Built Trailside Chalet in The Brook - direct access to CAMBA/Birkie Trails

Newly Built Trailside Chalet in The Brook - direct access to CAMBA/Birkie Trails

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

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

Hayward, Round Lake Retreat. 4 Season

Hayward, Round Lake Retreat. 4 Season

Hayward Lakefront - Gorgeous Cabin, Four Seasons of Fun for up to 21 guests

Hayward Lakefront - Gorgeous Cabin, Four Seasons of Fun for up to 21 guests

Lakefront Wisconsin Cabin with Boat Dock!

Lakefront Wisconsin Cabin with Boat Dock!

Cozy Cabin on Secluded Peninsula

Cozy Cabin on Secluded Peninsula

On a 3200 acre lake with 400 ft of frontage. Great fishing kayaking boating fun

On a 3200 acre lake with 400 ft of frontage. Great fishing kayaking boating fun

Pet-Friendly Lakeside Cabin with Kayaks and Canoe!

Pet-Friendly Lakeside Cabin with Kayaks and Canoe!

Lake Hayward. Private Lakefront Within Walking Distance To Downtown Hayward

Lake Hayward. Private Lakefront Within Walking Distance To Downtown Hayward

Phillips Cabin w/ Lake Views & Private Dock!

Phillips Cabin w/ Lake Views & Private Dock!

Round Lake Cabin Retreat

Round Lake Cabin Retreat

Avail. Valentine's w/Hot Tub, WIFI, King Beds

Avail. Valentine's w/Hot Tub, WIFI, King Beds

Lakeside cabin retreat; perfect getaway for winter sports, four seasons of fun

Lakeside cabin retreat; perfect getaway for winter sports, four seasons of fun

Family Friendly Cottage w/Spectacular Views of Round Lake-Hayward, WI

Family Friendly Cottage w/Spectacular Views of Round Lake-Hayward, WI

North Fork Flambeau River near Park Falls, 3BR, 1BA country home, on ATV route.

North Fork Flambeau River near Park Falls, 3BR, 1BA country home, on ATV route.

Other types of properties in Winter you may be interested in

Spacious Winter Retreat w/ River Access + Kayaks!

Spacious Winter Retreat w/ River Access + Kayaks!

Bears Den on the private lake

Bears Den on the private lake

Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

Find out more about Winter

Find out more about Winter

Recent reviews of Winter properties

Recent reviews of Winter properties

Newly Built Trailside Chalet in The Brook - direct access to CAMBA/Birkie Trails

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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