Winter Holiday Rentals

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Holiday Rentals in Winter

Telemark Northwoods Lodging

3.5 star property
Cable
9.0 out of 10, Wonderful, (316)
"Great room excellent people to worh with."
United States
Doyle
The price is NZ$548
includes taxes & fees
27 Nov - 28 Nov
Telemark Northwoods Lodging

Charming 2-bedroom house located in Ojibwa WI just off the Tuscobia Trail.

2.0 star property
Ojibwa
10.0 out of 10, Exceptional, (12)
"Very cozy, perfect for a family. Had everything we needed. "
United States
Erica C.
The price is NZ$344
includes taxes & fees
19 Nov - 20 Nov
Charming 2-bedroom house located in Ojibwa WI just off the Tuscobia Trail.

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

2.0 star property
Hawkins
9.8 out of 10, Exceptional, (16)
"Was a nice and quiet place. Was very impressed with the place!!!!"
United States
Hannah
The price is NZ$269
includes taxes & fees
18 Nov - 19 Nov
Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails.

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

Hayward
8.8 out of 10, Excellent, (27)
"Kind of run down, needing some updating. Shower worked but not in good condition."
United States
Kathy L.
The price is NZ$241
includes taxes & fees
18 Nov - 19 Nov
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage

Red Pines - Elk Lake #6A | Studio, 1 Bath

Phillips
9.4 out of 10, Exceptional, (10)
"Very clean and comfortable place to stay"
United States
Melane O.
The price is NZ$267
includes taxes & fees
1 Dec - 2 Dec
Red Pines - Elk Lake #6A | Studio, 1 Bath

Chip-Wa Lodging Room 1

Hunter
10.0 out of 10, Exceptional, (2)
"Great"
United States
James L.
The price is NZ$286
includes taxes & fees
2 Dec - 3 Dec
Chip-Wa Lodging Room 1

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

Phillips
9.4 out of 10, Exceptional, (21)
"Beautiful waterfront property that is very spacious and well maintained. Great location close to restaurant/bar."
United States
Judi M.
The price is NZ$217
includes taxes & fees
18 Nov - 19 Nov
Lakefront cottage w/ convenient access to restaurants, atv and snowmobile trails

Motorsports Basecamp near lakes and forest

Hayward
9.8 out of 10, Exceptional, (29)
"This was a nice cabin. We brought up spices for our meals but there were many additional ones for us to use in cooking. Plenty of pots/pans/dishes. Fire pit is great on a chilly night."
United States
Jenni K.
The price is NZ$475
includes taxes & fees
18 Nov - 19 Nov
Motorsports Basecamp near lakes and forest

Rustic campground in Butternut

1.0 star property
Butternut
The price is NZ$121
includes taxes & fees
18 Nov - 19 Nov
Rustic campground in Butternut

Rock Garden Wisconsin Concrete Park | 3 Beds, comfortable and clean

2.0 star property
Phillips
9.6 out of 10, Exceptional, (5)
"We enjoyed our stay very much. Nice deck to sit and enjoy the outdoors. Very peaceful looking at the trees out back."
United States
Carol D.
Rock Garden Wisconsin Concrete Park | 3 Beds, comfortable and clean

Ladysmith Cozy Cottage - Copper Tub - Waterfront

2.0 star property
Ladysmith
10.0 out of 10, Exceptional, (2)
"Booked this place for me and my girlfriend to get away, relax, and recharge after the holidays. This Cozy Cottage was just the thing. We had a fantastic time and everything was as advertised. Would recommend this place to anyone looking to visit the Ladysmith, WI area."
United States
Jesse K.
The price is NZ$439
includes taxes & fees
18 Nov - 19 Nov
Ladysmith Cozy Cottage - Copper Tub - Waterfront

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

Butternut
10.0 out of 10, Exceptional, (74)
"Ice fishing, snowmobiling or just relaxing is all that and a bag of chips!"
United States
Dev B.
The price is NZ$559
includes taxes & fees
18 Nov - 19 Nov
Blissful cozy, year round, lakeside cabin on Butternut Lake. Dogs welcome.

Red Pines - Elk Lake Condo #4 | 2 Bed, 1 Bath

Phillips
10.0 out of 10, Exceptional, (1)
"We had a very short stay but it was great from check-in to check-out. Great communication, extremely clean and very cozy. A true Northwoods experience!"
United States
Rachel K.
The price is NZ$370
includes taxes & fees
18 Nov - 19 Nov
Red Pines - Elk Lake Condo #4 | 2 Bed, 1 Bath

Lake Front Cabin, Media/Game Room, Connects to Trails--NEWLY REMODELED

Hayward
10.0 out of 10, Exceptional, (8)
"Excellent property, exceptional hosts. "
United States
Michael H.
The price is NZ$635
includes taxes & fees
18 Nov - 19 Nov
Lake Front Cabin, Media/Game Room, Connects to Trails--NEWLY REMODELED

NEW|AvailableThanksgiving-King Bed, Pacman, EV

Hayward
9.6 out of 10, Exceptional, (11)
"Beautiful "
United States
Tammy R.
The price is NZ$630
includes taxes & fees
18 Nov - 19 Nov
NEW|AvailableThanksgiving-King Bed, Pacman, EV

Red Pines - Elk Lake Condo #1 | 3 Bedroom, 1.5 Bath

Phillips
10.0 out of 10, Exceptional, (13)
"Fantastic Place !!!!!! It was great and exactly what we needed!"
United States
Ryan
The price is NZ$370
includes taxes & fees
1 Dec - 2 Dec
Red Pines - Elk Lake Condo #1 | 3 Bedroom, 1.5 Bath

The Bunkhouse, cozy studio in adorable Ladysmith. Escape to the Northwoods!

2.0 star property
Ladysmith
The price is NZ$260
includes taxes & fees
1 Dec - 2 Dec
The Bunkhouse, cozy studio in adorable Ladysmith. Escape to the Northwoods!

Wiggle Weigel Lodges

Ladysmith
9.6 out of 10, Exceptional, (4)
"Nice quiet area in a good location."
United Kingdom
Jeff R.
The price is NZ$681
includes taxes & fees
18 Nov - 19 Nov
Wiggle Weigel Lodges

Lady Lake Retreat on Cavanaugh Bay w/Hot Tub&Sauna

2.0 star property
Hayward
The price is NZ$980
includes taxes & fees
18 Nov - 19 Nov
Lady Lake Retreat on Cavanaugh Bay w/Hot Tub&Sauna

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

Hayward
8.8 out of 10, Excellent, (8)
"The property is beautiful and secluded from the hustle and bustle. The family running it are working hard to make improvements to the property and I think they will enhance the overall experience. If there were any negatives, the wifi signal didn't work. It wouldn't have been an issue but we didn't have a Verizon signal either so it wasn't as relaxing of an experience because I was worried about work (I work at an emergency response company and being disconnected is difficult). On the other...
United States
Andrew G.
The price is NZ$241
includes taxes & fees
18 Nov - 19 Nov
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
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.
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Top Winter Hotel Reviews

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$548 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. 

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.

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 Fishtrap 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.