Winter Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Winter

Interior
Spacious Winter Retreat w/ River Access + Kayaks!
8.6 out of 10, Excellent, (7)
"This was a great place to stay for a group of friends. The game room and bar area was a lot of fun. The property manager responded very quickly and was easy to work with. My only critique is that the kitchen area could use a bit of filling out, with effectively no consumables or spices available and an odd scattering of kitchen tools/pans, with heavy wear."
Spacious Winter Retreat w/ River Access + Kayaks!
Dining
Bears Den on the private lake
9.6 out of 10, Exceptional, (24)
"Everything went smooth. Nice place. Very involved owner that insured a pleasant stay."
Bears Den on the private lake
Exterior
Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin
8.4 out of 10, Very good, (11)
"A family owned business, the owner and his family made me feel very welcomed and looked after. It was a perfect place to relax and recharge."
Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin
Save an average of 15% on thousands of hotels when you're signed in
TV, fireplace, DVD player, books
GREAT PLACE OPENS JULY 7
6.0 out of 10, (6)
"/ My mother and I booked this property to celebrate her 65th birthday, get away from the Hussle and bustle of daily life and to enjoy the peace and quiet . we drive over 4 hours to a place without cell phone service so we could have peace. The day before bill called me and when I told him it would be after 7pm when we would be there he offered on his own to prepare dinner for us so we wouldn't have to cook. That was the last good thing I can say about our stay. The cabin grounds were...
GREAT PLACE OPENS JULY 7
Deluxe Suite, 1 Bedroom, Kitchen | Terrace/patio
Telemark Northwoods Lodging
3.5 star property
9.0 out of 10, Wonderful, (198)
"I had an amazing stay. The property was nestled into a quiet wooded lot and was a relaxing space. The room was clean and welcoming with all the amenities I needed for a weekend stay. I enjoyed having a kitchen to prepare my own food. The proximity to Cable made the location convenient. "
The price is NZ$187
includes taxes & fees
26 May - 27 May
Telemark Northwoods Lodging
Dining
Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!
9.6 out of 10, Exceptional, (165)
"My boyfriend and I stayed at this cabin for our anniversary trip. The cabin was in a beautiful location right on the lake with only 1 visible neighbor. Neighborhood was quiet. Cabin very clean and had everything you need in a cabin. Beds very comfy! Only about 10 mins outside of town for easy access. Cozy, relaxing, romantic. So romantic that my boyfriend decided to propose to me on this trip 😀 This spot will forever hold a special place in our hearts. Highly recommend!"
Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!
Property grounds
Northwoods multiple family size cabin. ATV/UTV, snowmobile trail access and lake
10.0 out of 10, Exceptional, (22)
"This cabin was a perfect fit for our family of 14, ranging in age from 1 to 60. There was plenty of room for all of us, the yard was HUGE, and the hosts were so responsive and friendly. Sand Lake was fun for fishing and the sandbar at the dock made for a great place for all our young ones to play in the water safely. They had everything we needed for a great vacation."
Northwoods multiple family size cabin. ATV/UTV, snowmobile trail access and lake
Interior
Cozy Cabin on Secluded Peninsula
9.8 out of 10, Exceptional, (27)
"Very nice cabin. Quiet location. Book it you will love it."
Cozy Cabin on Secluded Peninsula
Fridge, microwave, oven, stovetop
Solitude and seclusion welcome you to this modern chalet nestled in the woods
10.0 out of 10, Exceptional, (38)
"Place is great. Right on the trail. If peace and quiet are what you need there is all kinds of that at this place. Will stay here again!"
Solitude and seclusion welcome you to this modern chalet nestled in the woods
Property grounds
Peaceful cabin on the Flambeau River
10.0 out of 10, Exceptional, (108)
"An amazing place to stay. Clean, comfortable, secluded but convenient to town. This place is a winner!"
Peaceful cabin on the Flambeau River
Property grounds
Spacious Lake Home near Ladysmith, with a private dock on the Dairyland Flowage!
10.0 out of 10, Exceptional, (12)
"We enjoyed our stay in this home. The lake view we had was beautiful and even more beautiful because of the snow. We were in town for some family emergency services but we still enjoyed our time and felt very relaxed even with the family circumstances. We took lots of pictures and enjoyed every minute we could. The home is well stocked with pans and supplies."
Spacious Lake Home near Ladysmith, with a private dock on the Dairyland Flowage!
Fridge, microwave, oven, stovetop
North Fork Flambeau River near Park Falls, 3BR, 1BA country home, on ATV route.
10.0 out of 10, Exceptional, (2)
"The property, though older, has been well maintained and was spotless. There was plenty of space, and the view out the huge picture window over the water was spectacular. Communication with the host was great, and Michelle was so kind, especially when we couldn't get the door opened the first time. Other than coffee and wine, kitchen amenities are limited, but we had everything we needed to make simple meals. I have never seen so many bath amenities in my life. I enjoyed two soaks in the tub. My...
North Fork Flambeau River near Park Falls, 3BR, 1BA country home, on ATV route.
Exterior
Sauna Rental, Game Table, Fireplace, 2 King Beds
10.0 out of 10, Exceptional, (31)
"My mom and I had a wonderful time our 10 days there. Smooth check-in, exceptionally clean and all the amenities at our fingertips. We loved that it was secluded—not another person in sight. We looooved the wood burning fireplace the most and enjoyed many fires. There were so many extra things that we didn’t take advantage of, but love if we come back in warmer weather—kayak, canoe, outdoor firepit with comfy Adirondack chairs, and even the Bags yard game. Any questions we had were answered...
The price is NZ$635
includes taxes & fees
28 May - 29 May
Sauna Rental, Game Table, Fireplace, 2 King Beds
Lake
Lake Hayward. Private Lakefront Within Walking Distance To Downtown Hayward
9.8 out of 10, Exceptional, (95)
"Great house, clean, comfortable bed, well-stocked, can’t beat the location, deer in the front yard & lake right out the back door! Good communication! Highly recommend!"
Lake Hayward. Private Lakefront Within Walking Distance To Downtown Hayward
Property grounds
Burns Lake Cabin w/ Dock, Fire Pit, Rowboat & More
8.6 out of 10, Excellent, (29)
"Secluded enough from other neighbors but close to Hayward for short day trips. The cabin is well equipped with everything we needed, and very reasonable house rules. This was our second stay at this property (two years in a row) and will definitely consider again."
Burns Lake Cabin w/ Dock, Fire Pit, Rowboat & More
Exterior
Pet-Friendly Lakeside Cottage with Kayaks and a Canoe!
10.0 out of 10, Exceptional, (39)
"We had our entire family (6 adults and our 14 month old Granddaughter) had such a wonderful time! We kayaked, fished and just enjoyed the natural splendor! For a small little lake holy smokes it was so much fun watching the fishing activity! Loved everything! Brad our property owner was so highly communicative and I certainly appreciate everything he did for us! I honestly wish that there was a higher level we could give! 👍"
Pet-Friendly Lakeside Cottage with Kayaks and a Canoe!
Fridge, microwave, stovetop, dishwasher
Phillips Cabin w/ Lake Views & Private Dock!
10.0 out of 10, Exceptional, (10)
"We had a wonderful time property was over and above expected. Very clean, beautiful property, everything we needed."
Phillips Cabin w/ Lake Views & Private Dock!
Dining
Scenic Hayward Lake View Retreat w/ Fire Pit
10.0 out of 10, Exceptional, (3)
"We had our girls weekend ( 11 of us ) wonderful property !!!"
Scenic Hayward Lake View Retreat w/ Fire Pit
Fridge, microwave, oven, stovetop
Pet-Friendly Lakeside Chalet with Kayaks, Canoe, and Pedal Boat!
10.0 out of 10, Exceptional, (81)
"Wonderful property we looked our weekend their."
Pet-Friendly Lakeside Chalet with Kayaks, Canoe, and Pedal Boat!
Property grounds
Pet-Friendly Lakeside Cabin with Kayaks, Canoe, and Pedal Boat!
10.0 out of 10, Exceptional, (101)
"Every year we take a trip up this way, this cabin was perfect our kids loved the game room!"
Pet-Friendly Lakeside Cabin with Kayaks, Canoe, and Pedal Boat!
Don't see what you're looking for?
See all available properties in Winter
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.

Other types of properties in Winter you may be interested in

Interior
Spacious Winter Retreat w/ River Access + Kayaks!
8.6 out of 10, Excellent, (7)
"This was a great place to stay for a group of friends. The game room and bar area was a lot of fun. The property manager responded very quickly and was easy to work with. My only critique is that the kitchen area could use a bit of filling out, with effectively no consumables or spices available and an odd scattering of kitchen tools/pans, with heavy wear."
Spacious Winter Retreat w/ River Access + Kayaks!
Dining
Bears Den on the private lake
9.6 out of 10, Exceptional, (24)
"Everything went smooth. Nice place. Very involved owner that insured a pleasant stay."
Bears Den on the private lake
TV, fireplace, DVD player, books
GREAT PLACE OPENS JULY 7
6.0 out of 10, (6)
"/ My mother and I booked this property to celebrate her 65th birthday, get away from the Hussle and bustle of daily life and to enjoy the peace and quiet . we drive over 4 hours to a place without cell phone service so we could have peace. The day before bill called me and when I told him it would be after 7pm when we would be there he offered on his own to prepare dinner for us so we wouldn't have to cook. That was the last good thing I can say about our stay. The cabin grounds were...
GREAT PLACE OPENS JULY 7
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Winter holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Winter. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Winter. Seeing all the best attractions is bound to make you fall in love with Winter. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Winter short-term rentals, that won’t be hard to do.

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 13 Expedia holiday rentals in Winter for a memorable holiday.

What can I see and do in Winter?

Chequamegon National Forest and Flambeau River are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find Ojibwa State Park and Lake Chippewa.

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.

Recent reviews of Winter properties
Expedia verified reviews