Search Vacation Homes in Winter

  • 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

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

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, (17)
"Good location, plenty of space for everyone."
Ackwood Lodge - The Lodge, LARGE, Private Lakeshore Estate. Perfect for Family Reunions

Club Suite Recreational Retreat

10.0 out of 10, Exceptional, (16)
"We really enjoyed our stay. It was perfect for what we needed for size and all the extra things that are there for guests is great! "
Club Suite Recreational Retreat

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

9.8 out of 10, Exceptional, (20)
"Location was amazing, the house was very cabin like which my family liked. "
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)
"Nice and clean, great sandy swimming area for little ones in the family"
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)
"Annual fishing trip. Good dock space, close to water, very private."
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, (54)
"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)
"Very clean and spacious- well stocked property perfect for family to spread out."
Paradise Shores & Fish Galore ~private small beach & dock!

THE 1852 LOG HOUSE.

10.0 out of 10, Exceptional, (31)
"This is our second stay at the cabin. It's a wonderful place to stay with easy access to Hayward and all the local lakes. Great clean place with tons of supplies for cooking. We especially love it as a place to stay while visiting our kids at camp."
THE 1852 LOG HOUSE.

New cabin on Lac Courte Oreilles!!

9.8 out of 10, Exceptional, (29)
"Great little lake cabin!"
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

Birchwood Haven-Wooded Lakefront Cabin Retreat on Lake Chetac, Birchwood WI

10.0 out of 10, Exceptional, (9)
"We had a great time on our family vacation week at this home! The home was perfect for 3 families and was as advertised. We also very much enjoyed the lake and Birchwood area. Lots to do for the adults and children. We would definitely stay here again! "
The price is AED 2,075
AED 3,608 total
includes taxes & fees
8 Jun - 9 Jun
Birchwood Haven-Wooded Lakefront Cabin Retreat on Lake Chetac, Birchwood WI

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 AED 798
AED 2,062 total
includes taxes & fees
12 May - 13 May
Lakefront Cabin on LCO - The Sunset Escape

Executive Custom Log Lodge on Little Round Lake

10.0 out of 10, Exceptional, (91)
"Comfortable, beautiful property!"
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)
"It was a very enjoyable stay, and the house was very homely."
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)
"We have stayed at this property several times and really love the place, its location and all the amenities. Highly recommend!"
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)
"Had a great time"
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, (16)
"Nice, cozy and clean cabin in a perfect location."
The price is AED 643
AED 1,492 total
includes taxes & fees
9 May - 10 May
Renovated cabin on Lac Courte Oreilles Lake - minutes from trails!

2 cozy, secluded cabins on beautiful waterfront acreage with epic game room

10.0 out of 10, Exceptional, (5)
"This cabin was a great find and was perfect for what we were looking for. The hosts were amazing with communication and the game room is fantastic! Very kid friendly place if you have kiddos. This was perfect for a getaway and we played camp games for a bachelorette party. "
2 cozy, secluded cabins on beautiful waterfront acreage with epic game room
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.
Don't see what you're looking for?
See all available properties in Winter
Save an average of 15% on thousands of hotels when you're signed in

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

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

9.8 out of 10, Exceptional, (54)
"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)
"Well outfitted cabin - had a group of 10 and had plenty of space, cooking-ware, and plates. Hosts were very responsive. Kids enjoyed splashing in the water and swimming back and forth from the swim platform. Would stay again."
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.