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Compare 149 Vacation Homes in Winter with updated reviews, rates, and availability.

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

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

Club Suite Recreational Retreat

10.0 out of 10, Exceptional, (16)
"Very clean and well appointed. We will stay again."
Club Suite Recreational Retreat

Little house in the woods but only 5 minutes from town!

9.8 out of 10, Exceptional, (20)
"Mandi’s up north cabin is a great place for a quite getaway but still plenty to do in the area. The cabin is very clean, updated and very roomy. We had a great New Year’s Eve bonfire. Thanks so much!!!"
Little house in the woods but only 5 minutes from town!

Lakeshore Pines | Peaceful, Lakefront Seclusion | 2 Bedroom

9.8 out of 10, Exceptional, (15)
"This is our third time staying at this cozy wonderful cabin! We’ve been owners of two rentals in the past so we know about running a great facility and this one incredible!!! Our only suggestion would be to have some basic condiments.. THANK YOU!!!"
Lakeshore Pines | Peaceful, Lakefront Seclusion | 2 Bedroom

Northwood's Fish Haven on Beautiful Moose Lake; 2 kayaks, Lilly pad & game-room

9.6 out of 10, Exceptional, (90)
"The house was clean and beautifully set up for a great vacation! Fishing was a little rough but we landed enough to have a good meal. Overall my wife and I had a nice, relaxing lake home vacation."
Northwood's Fish Haven on Beautiful Moose Lake; 2 kayaks, Lilly pad & game-room

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.

North Fork Flambeau River near Park Falls, 3BR, 1BA country home, on ATV route.

9.6 out of 10, Exceptional, (11)
"This was a nice location with a great view "
North Fork Flambeau River near Park Falls, 3BR, 1BA country home, on ATV route.

Paradise Shores & Fish Galore ~private small beach & dock!

10.0 out of 10, Exceptional, (103)
"Wonderful place - clean, bright, full of everything we needed. The beds were comfortable, kitchen full of everything I needed to cook meals and in a beautiful setting! Thank you for sharing your beautiful home with us! "
Paradise Shores & Fish Galore ~private small beach & dock!

THE 1852 LOG HOUSE.

10.0 out of 10, Exceptional, (31)
"The hosts were wonderful and the cabin was excellently appointed to be able to properly cook great meals. Everything in the kitchen you could need is there for use. Be mindful that this cabin sits on regulaly travelled road, so expect some quick road traffic"
THE 1852 LOG HOUSE.

New cabin on Lac Courte Oreilles!!

9.8 out of 10, Exceptional, (29)
"Couldn’t have been happier with this cozy cabin. We enjoyed the stars on the dock, had a fire in the firepit, and loved the accommodations. The beds were really comfy and the vintage details were great! Would definitely come back again!"
New cabin on Lac Courte Oreilles!!

"Ol Man Wavin Haven" home that has road access to UTV, ATV and snowmobile trails

9.8 out of 10, Exceptional, (11)
"Place was very clean. Lots of room. Will stay again."
"Ol Man Wavin Haven" home that has road access to UTV, ATV and snowmobile trails

Wooded Lakefront Home: Nestled in the natural beauty of Birchwood, Wisconsin

10.0 out of 10, Exceptional, (9)
"A beautiful winter location and property. Spacious, inviting and comfortable home. Friendly, helpful and responsive hosts."
Wooded Lakefront Home: Nestled in the natural beauty of Birchwood, Wisconsin

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

Lakefront Cabin on LCO - The Sunset Escape

10.0 out of 10, Exceptional, (2)
"Was exactly what it said it was. Had a great time and everything was very nice. My girlfriend and I had a great time."
The price is SAR 686
SAR 1,936 total
includes taxes & fees
7 Apr - 8 Apr
Lakefront Cabin on LCO - The Sunset Escape

Executive Custom Log Lodge on Little Round Lake

10.0 out of 10, Exceptional, (91)
"We ALL LOVED your place!!!! Absolutely BEAUTIFUL, comfortable, so much space! We were a group of 9 couples and were very pleased! Would definitely stay here again!!!!"
Executive Custom Log Lodge on Little Round Lake

Secluded Log Home in the NATIONAL FOREST. ATV TRAILS CROSS OUR PROPERTY

9.6 out of 10, Exceptional, (138)
"This will be 25 yrs + for our group of guys annual hunting and fishing trip staying in the area. This is our 2nd year here and all the guys commented that this is the best place so far. It is close to all our favorite hunting and fishing spots and is the most spacious place we have ever stayed with plenty of room for all our gear and to spread out. The huge yard and endless woods to explore at the back door is amazing as well as the beautiful Ghost Creek that leads you to the Chippewa. This...
Secluded Log Home in the NATIONAL FOREST. ATV TRAILS CROSS OUR PROPERTY

Upscale Lake Home on Beautiful 915 Acre Solberg Lake, Phillips WI

9.8 out of 10, Exceptional, (131)
"Stayed with a bunch of friends for an icefishing weekend. Great fishing on solberg and excellent cabin. "
Upscale Lake Home on Beautiful 915 Acre Solberg Lake, Phillips WI

Elk Lodge on Fir, beautiful home with lake access

10.0 out of 10, Exceptional, (6)
"This house was such a great spot for our family weekend away. We had kids and adults who were able to spread out and have their own space or come together for meals and games. The huge kitchen and living space upstairs was so nice and open and the game room downstairs was a great activity option. I would highly recommend this place. "
Elk Lodge on Fir, beautiful home with lake access

Renovated cabin on Lac Courte Oreilles Lake - minutes from trails!

10.0 out of 10, Exceptional, (15)
"Incredible place to stay for a cozy weekend full of snow activities with our family. Beautiful cabin and fully furnished kitchen with everything we needed for meals in, cards/board games (for all ages) to help unplug and incredible views of the lake! Great communication from host before, during, and after our stay! Couldn't ask for a better place to stay. "
The price is SAR 563
SAR 1,410 total
includes taxes & fees
13 Apr - 14 Apr
Renovated cabin on Lac Courte Oreilles Lake - minutes from trails!
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 property types 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 .

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!
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.