Winter Vacation Rentals

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Vacation Rentals in Winter

Spacious Winter Retreat w/ River Access + Kayaks!
8.6 out of 10, Excellent, 7 reviews
"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!
Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin
8.4 out of 10, Very good, 11 reviews
"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
Bears Den on the private lake
9.6 out of 10, Exceptional, 24 reviews
"Everything went smooth. Nice place. Very involved owner that insured a pleasant stay."
Bears Den on the private lake
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GREAT PLACE OPENS JULY 7
6.0 out of 10, 6 reviews
"/ 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
Telemark Northwoods Lodging
3.5 star property
9.0 out of 10, Wonderful, 203 reviews
"Loved the location -very quiet and off the beaten path, but close to Cable. Just a short walk from your door to the Birkebeiner trails for a beautiful walk or bike ride. It was great to have a fully equipped kitchen!"
The price is CA $164
CA $180 total
includes taxes & fees
Jun 18 - Jun 19
Telemark Northwoods Lodging
Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!
9.6 out of 10, Exceptional, 167 reviews
"What a wonderful cottage with an outstanding lake view! All kinds of wildlife - geese, loons, mallards, herons, turtles, and beaver. A young bald eagle visited the property several times. The cottage was very clean and comfortable. WiFi test indicated 20MB download - no problems streaming on our Roku."
Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!
Northwoods multiple family size cabin. ATV/UTV, snowmobile trail access and lake
10.0 out of 10, Exceptional, 22 reviews
"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
Peaceful cabin on the Flambeau River
10.0 out of 10, Exceptional, 108 reviews
"An amazing place to stay. Clean, comfortable, secluded but convenient to town. This place is a winner!"
Peaceful cabin on the Flambeau River
Newly Built Trailside Chalet in The Brook - direct access to CAMBA/Birkie Trails
10.0 out of 10, Exceptional, 61 reviews
"Could not have chosen a nicer rental for a long weekend. Absolute peace and privacy, yet also close to town. Cabin was immaculate and comfortable. Watching turkeys run by while having morning coffee. Highest recommendation!"
Newly Built Trailside Chalet in The Brook - direct access to CAMBA/Birkie Trails
North Fork Flambeau River near Park Falls, 3BR, 1BA country home, on ATV route.
10.0 out of 10, Exceptional, 2 reviews
"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.
Pet-Friendly Lakeside Cabin with Kayaks, Canoe, and Pedal Boat!
10.0 out of 10, Exceptional, 102 reviews
"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!
Hayward Cabin on Grindstone Lake: Bring Your Boat!
8.2 out of 10, Very good, 24 reviews
"Lake Grindstone is a beautiful lake. I kayaked and played off the dock with my Welsh Terrier. That said, the cabin doesn’t make a good first impression as the deck is dirty and in need of a blowing off. The deck would not be safe for small children as there are gaps in the spindles. Could crawl and fall 8-10 feet. Couldn’t close the screen on the deck door off the LR; but was able to get it on the track using a butter knife. Satellite TV didn’t work. Nice kitchen and living space. Host contact...
Hayward Cabin on Grindstone Lake: Bring Your Boat!
Cozy Cabin on Secluded Peninsula
9.8 out of 10, Exceptional, 27 reviews
"Very nice cabin. Quiet location. Book it you will love it."
Cozy Cabin on Secluded Peninsula
Phillips Cabin w/ Lake Views & Private Dock!
10.0 out of 10, Exceptional, 10 reviews
"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!
Charming Butternut Lake Getaway w/ Deck & Dock!
Charming Butternut Lake Getaway w/ Deck & Dock!
Pet-Friendly Lakeside Chalet with Kayaks, Canoe, and Pedal Boat!
10.0 out of 10, Exceptional, 81 reviews
"Wonderful property we looked our weekend their."
Pet-Friendly Lakeside Chalet with Kayaks, Canoe, and Pedal Boat!
Sauna Rental, Game Table, Fireplace, 2 King Beds
10.0 out of 10, Exceptional, 33 reviews
"We had a great stay and hosts were great with communication. The property is just as described. Beautiful setting on the Chippewa River. The new hot tub was a big hit with our family. Very relaxing. We enjoyed playing some of the provided games and even ordered a couple we really liked. We had our 1 yr old grandson with and was so thankful to have the high chair, toys, etc available. Sitting by the double sided fire to wrap up and start our days was wonderful. Would like to stay again in...
The price is CA $695
CA $831 total
includes taxes & fees
Jul 2 - Jul 3
Sauna Rental, Game Table, Fireplace, 2 King Beds
Cozy log home on 6 acres - Hayward
10.0 out of 10, Exceptional, 106 reviews
"This is a great place to stay with friends or family. There is great trails all around to ride. The cabin was so clean and relaxing, perfect for our trip!"
Cozy log home on 6 acres - Hayward
Lake Hayward. Private Lakefront Within Walking Distance To Downtown Hayward
9.8 out of 10, Exceptional, 95 reviews
"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
Family Friendly Cottage w/Spectacular Views of Round Lake-Hayward, WI
10.0 out of 10, Exceptional, 102 reviews
"Great house. Awesome 3 seasons room."
Family Friendly Cottage w/Spectacular Views of Round Lake-Hayward, WI
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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

Spacious Winter Retreat w/ River Access + Kayaks!
8.6 out of 10, Excellent, 7 reviews
"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!
Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin
8.4 out of 10, Very good, 11 reviews
"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
Bears Den on the private lake
9.6 out of 10, Exceptional, 24 reviews
"Everything went smooth. Nice place. Very involved owner that insured a pleasant stay."
Bears Den on the private lake
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.

Everything you need to know about Winter vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winter vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winter vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winter vacation rentals we have selected for you start as low as CA $164 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 vacation 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 vacation.

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 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?

Spacious Winter Retreat w/ River Access + Kayaks!: Visitors give good reviews to this Winter vacation home rental, which offers a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games. Our travelers also rate Bears Den on the private lake as a favorite home for rent in Winter.

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?

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

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.

Recent reviews of Winter properties
Expedia verified reviews