Winter Holiday Rentals

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Holiday Rentals in Winter

Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

8.8 out of 10, Excellent, (17)
"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! "
Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

Luxury Cabin, 800+ feet frontage, 733 acre Lake, Hot tub, Pontoon, Fireplace .

10.0 out of 10, Exceptional, (19)
"Highly recommend for a Wisconsin North Woods getaway. Luxurious accommodations in a serene environment, very close to a village with basic amenities "
Luxury Cabin, 800+ feet frontage, 733 acre Lake, Hot tub, Pontoon, Fireplace .

6 bedroom 3- bath 16 people capacity pontoon included in Winter Wis.

9.8 out of 10, Exceptional, (53)
"WILL NEED TO GO BACK IN THE SUMMER TO ENJOY THE LAKE "
6 bedroom 3- bath 16 people capacity pontoon included in Winter Wis.

Bears Den on the private lake

9.6 out of 10, Exceptional, (26)
"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."
Bears Den on the private lake

Spacious Winter Retreat w/ River Access + Kayaks!

9.2 out of 10, Wonderful, (19)
"Perfect cabin in the woods! Has a great scenic spot on the river and plenty of space for guests. Awesome game room and bar area as advertised. Teresa was a great host and was very helpful throughout the process. Would definitely come back! "
Spacious Winter Retreat w/ River Access + Kayaks!

Telemark Northwoods Lodging

3.5 star property
9.0 out of 10, Wonderful, (268)
"A hidden gem!"
The price is NZ$256
includes taxes & fees
4 May - 5 May
Telemark Northwoods Lodging

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

9.8 out of 10, Exceptional, (186)
"We have rented this cabin before and have always been very happy with everything about it. Plan to rent again in the future."
Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!

Round Lake Cabin Retreat

9.4 out of 10, Exceptional, (64)
"Great space for guiding a yoga class on the main floor. Had a blanket of snow fall so we had a great time with our snowshoes and cross country skis. Prepared some delicious meals using the kitchen. My friends enjoyed the space."
Round Lake Cabin Retreat

Backyard Trails and Lake Hayward with Canoe!

9.4 out of 10, Exceptional, (23)
"Great landing spot for our time in Hayward competing in a youth hockey tournament. "
Backyard Trails and Lake Hayward with Canoe!

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

9.8 out of 10, Exceptional, (26)
"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."
Northwoods multiple family size cabin. ATV/UTV, snowmobile trail access and lake

Rustic and Charming one Bedroom cabin. Upgraded pontoon!

9.8 out of 10, Exceptional, (86)
"This was our 3rd stay! We love it. "
Rustic and Charming one Bedroom cabin. Upgraded pontoon!

Book your summer cabin now! Between 2 Great Lakes outside of Hayward!

9.0 out of 10, Wonderful, (18)
"Location was perfect for the race and the price was right. Listing said room for 6, which was technically accurate but it was difficult to see that the beds were not very private. Only one bed has privacy. Other than that I found the place a fantastic deal and the host was wonderful at communicating. Had a nice patio and fire pit to relax"
Book your summer cabin now! Between 2 Great Lakes outside of Hayward!

Beautiful Ponderosa Pine Log Cabin - Northwoods Retreat On 10 Acres

10.0 out of 10, Exceptional, (251)
"we enjoyed our 3 night stay hot tube was nice was a chilly rainy snowy weekend fireplace was awesome to sit around stay warm would go back and stay again "
Beautiful Ponderosa Pine Log Cabin - Northwoods Retreat On 10 Acres

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

9.6 out of 10, Exceptional, (11)
"Your place worked great for our group on our last night in the Northwoods!"
The price is NZ$237
includes taxes & fees
20 Apr - 21 Apr
Lakefront cottage w/ convenient access to restaurants, atv and snowmobile trails

Remodeled Lakefront Cabin w/ Pool Table: Northwoods Nostalgia + Modern Amenities

2.0 star property
10.0 out of 10, Exceptional, (13)
"We had 2 family’s and it was a perfect fit for us. The owners were great at communicating with us and very accommodating to our requests. We would definitely highly recommend. "
Remodeled Lakefront Cabin w/ Pool Table: Northwoods Nostalgia + Modern Amenities

Phillips Cabin w/ Lake Views & Private Dock!

9.8 out of 10, Exceptional, (22)
"Property was exactly as advertised. Everything was clean and well organized. Fish weren’t biting but oh well…"
Phillips Cabin w/ Lake Views & Private Dock!

Cabin with private dock and large yard space!

9.6 out of 10, Exceptional, (44)
"Very good location for fishing. Lucas was ver easy to work with. We had a very good fishing trip.Thank you"
Cabin with private dock and large yard space!

Lena's Northern Pines Resort

3.0 star property
8.0 out of 10, Very good, (1)
"Nice location near the lake only downside was mold on wall in bathroom and couldn't get tv remote to work "
The price is NZ$254
includes taxes & fees
3 May - 4 May
Lena's Northern Pines Resort

Cozy, Rustic Luxury Cabin on Round Lake, with all of the modern conveniences!

9.8 out of 10, Exceptional, (22)
"Great place! Lots of room for 2 families. Easy in and out for the races. Great kitchen for cooking and two really nice bathrooms. "
Cozy, Rustic Luxury Cabin on Round Lake, with all of the modern conveniences!

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

10.0 out of 10, Exceptional, (55)
"Loved our stay for Birkie weekend!"
The price is NZ$994
includes taxes & fees
1 May - 2 May
Hayward, Round Lake Retreat! Private dock, 3 kayaks, beautifully maintained!
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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Other types of properties in Winter you may be interested in

Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

8.8 out of 10, Excellent, (17)
"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! "
Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

Luxury Cabin, 800+ feet frontage, 733 acre Lake, Hot tub, Pontoon, Fireplace .

10.0 out of 10, Exceptional, (19)
"Highly recommend for a Wisconsin North Woods getaway. Luxurious accommodations in a serene environment, very close to a village with basic amenities "
Luxury Cabin, 800+ feet frontage, 733 acre Lake, Hot tub, Pontoon, Fireplace .

6 bedroom 3- bath 16 people capacity pontoon included in Winter Wis.

9.8 out of 10, Exceptional, (53)
"WILL NEED TO GO BACK IN THE SUMMER TO ENJOY THE LAKE "
6 bedroom 3- bath 16 people capacity pontoon included in Winter Wis.
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.

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?

6 bedroom 3- bath 16 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. Some other homes for rent in Winter include Bears Den on the private lake and Spacious Winter Retreat w/ River Access + Kayaks!.

How many holiday rentals are there in Winter?

Choose from 11 Expedia holiday rentals in Winter for a memorable holiday.

What can I see and do in Winter?

Lake Winter and Chequamegon National Forest are a couple of lovely local spots to get outside and enjoy nature. Flambeau River and Ojibwa State Park 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.