Winter Holiday Rentals

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Holiday Rentals in Winter

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 .

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

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!

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

Telemark Northwoods Lodging

3.5 star property
9.0 out of 10, Wonderful, (268)
"A hidden gem!"
The price is NZ$266
includes taxes & fees
13 Apr - 14 Apr
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!

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

9.6 out of 10, Exceptional, (25)
"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

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

9.6 out of 10, Exceptional, (76)
"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."
Hayward Lakefront - Gorgeous Cabin, Four Seasons of Fun for up to 21 guests

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!

Ackwood Lodge - The Lodge, LARGE, Private Lakeshore Estate. Perfect for Family Reunions

10.0 out of 10, Exceptional, (18)
"We stayed at Ackwood Lodge for a long weekend celebrating my sister’s bachelorette. The accommodations were perfect for a larger party. Adam was great with communication and responded quickly. I would stay here again in a heartbeat!!"
Ackwood Lodge - The Lodge, LARGE, Private Lakeshore Estate. Perfect for Family Reunions

Beautiful Ponderosa Pine Log Cabin - Northwoods Retreat On 10 Acres

10.0 out of 10, Exceptional, (247)
"We had a very relaxing time. We wanted a winter getaway and this was perfect! We enjoyed the hot tub, relaxing by the fire and spending quality time together. Check in was easy and communication was great. We would stay again. "
Beautiful Ponderosa Pine Log Cabin - Northwoods Retreat On 10 Acres

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!

Charming 5 bedroom Lodge on Private Lake, Pet Friendly

9.8 out of 10, Exceptional, (23)
"Property was very big for 9 mid aged guys. Had plenty room for 3 trucks and trailers. Was very close to the snowmobile trails. Only issue was that I didn't read the rental agreement that said they didn't supply towels. Would definitely stay here again."
Charming 5 bedroom Lodge on Private Lake, Pet Friendly

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

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!

500' Lakeshore, 2 Docks, Sand Beach, Sleeps 10, A/C, Pontoon Boat for Rent

9.8 out of 10, Exceptional, (55)
"Nice roomy property for 6 fishermen to enjoy a few days on the water."
500' Lakeshore, 2 Docks, Sand Beach, Sleeps 10, A/C, Pontoon Boat for Rent

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!

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!

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

10.0 out of 10, Exceptional, (55)
"Loved our stay for Birkie weekend!"
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

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 .

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!

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
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. Our travellers also rate Spacious Winter Retreat w/ River Access + Kayaks! as a favourite home for rent in Winter.

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 Black Dan 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.