Holiday Homes in Winter

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Featured Holiday Homes in Winter

Our top choices for Winter holiday homes

Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails

2.0 star property
9.8 out of 10, Exceptional, (12)
"Was a nice and quiet place. Was very impressed with the place!!!!"
The price is AU$237
includes taxes & fees
1 Sept - 2 Sept
Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails

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

9.8 out of 10, Exceptional, (61)
"We had a wonderful time during our stay. The home was excellent for a large family. The waterfront was amazing with a great shoreline."
500' Lakeshore, 2 Docks, Sand Beach, Sleeps 10, A/C, Pontoon Boat for Rent

Paradise Shores & Fish Galore ~your own private beach & dock!

10.0 out of 10, Exceptional, (112)
"Very nice house great place to stay "
Paradise Shores & Fish Galore ~your own private beach & dock!

Executive Custom Log Lodge on Little Round Lake

10.0 out of 10, Exceptional, (99)
"Great space, well organized. So many options for things to do together as a family. Our large family of 22 people make it an annual trip there. It perfect for us"
Executive Custom Log Lodge on Little Round Lake

Breezy Bay Beach On Round Lake

10.0 out of 10, Exceptional, (58)
"Beautiful place to stay."
Breezy Bay Beach On Round Lake

Lakeshore Pines | Peaceful, Lakefront Seclusion | 2 Bedroom

10.0 out of 10, Exceptional, (21)
"Nice and clean, great sandy swimming area for little ones in the family"
Lakeshore Pines | Peaceful, Lakefront Seclusion | 2 Bedroom

5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.

10.0 out of 10, Exceptional, (63)
"Very nice property, lovely location, easy communication."
5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.

Cozy new cabin on Lac Courte Oreilles!!

9.6 out of 10, Exceptional, (40)
"Very clean cozy cabin in a great location!"
Cozy new cabin on Lac Courte Oreilles!!

Red Pines - Elk Lake #6A | Studio, 1 Bath

9.4 out of 10, Exceptional, (8)
"It was nice. Missed the sink in the bathroom, but for a quick stay, the kitchenette sink worked fine!"
The price is AU$235
includes taxes & fees
31 Aug - 1 Sept
Red Pines - Elk Lake #6A | Studio, 1 Bath

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

9.6 out of 10, Exceptional, (98)
"Great location- went up to snowmobile and very close to trail system."
Northwood's Fish Haven on Beautiful Moose Lake; 2 kayaks, Lilly pad & game-room

Charming 2-bedroom house located in Ojibwa WI just off the Tuscobia Trail.

2.0 star property
10.0 out of 10, Exceptional, (6)
"Excellent home, clean, exactly as described. Right off Tuscobia Trail. Lovely!"
The price is AU$305
includes taxes & fees
9 Sept - 10 Sept
Charming 2-bedroom house located in Ojibwa WI just off the Tuscobia Trail.

Sandalwood Retreat on Round Lake - Waterfront property with screened porch 

10.0 out of 10, Exceptional, (41)
"The house is clean, large enough for our entire family and a great location on Round Lake. We will for sure be staying here again! "
Sandalwood Retreat on Round Lake - Waterfront property with screened porch 

Private, secluded 2-bedroom house with King, Queen beds near Cable with WiFi, AC

9.4 out of 10, Exceptional, (3)
"My family of five rented this cabin for 4 days during the summer. We were very comfortable during our stay. The beds and pillows were new and comfortable and my daughter slept on the futon in the living room and said it was nice. The kitchen had all of the necessities to cook in. Paper products were provided which was a nice touch and the host even had snacks for us when we arrived. Overall we enjoyed our time here and would rent again. "
Private, secluded 2-bedroom house with King, Queen beds near Cable with WiFi, AC

Paradise on the Pixley

9.8 out of 10, Exceptional, (81)
"We had a lot of fun in the beautiful woods! We love it here and will keep coming back. "
Paradise on the Pixley

Elk Lodge on Fir, beautiful home with lake access

10.0 out of 10, Exceptional, (7)
"Had a great time"
Elk Lodge on Fir, beautiful home with lake access

Edgewater Retreat | 2 Bed, 2 Bath

10.0 out of 10, Exceptional, (8)
"Very comfortable stay. Sunset was gorgeous! Very nice home on the flowage. So quiet!"
Edgewater Retreat | 2 Bed, 2 Bath

Spruce Haven on Round Lake - Summer 2025 weeks available

9.6 out of 10, Exceptional, (13)
"We had a great time at this property. Very clean and newly renovated. Highly recommend!"
Spruce Haven on Round Lake - Summer 2025 weeks available

Breathe! A Beautiful Cabin | 2 Bed, 1 Bath

10.0 out of 10, Exceptional, (10)
"Great stay peaceful nice getaway"
Breathe! A Beautiful Cabin | 2 Bed, 1 Bath

Lake Hayward. Private Lakefront Within Walking Distance To Downtown Hayward

9.8 out of 10, Exceptional, (111)
"Very nice property on a lake great for paddle boarding. We had a great time."
Lake Hayward. Private Lakefront Within Walking Distance To Downtown Hayward

New cabin on Lac Courte Oreilles!!

10.0 out of 10, Exceptional, (37)
"A cute cabin on the lake. It was very clean and we enjoyed our stay."
New cabin on Lac Courte Oreilles!!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winter Hotel Reviews

Find out more about Winter

Find out more about Winter

Winter Holiday Homes information

Number of reviews
Accommodation
155 Holiday Homes
Lowest Price
AU$235
Highest Price
AU$305

Explore a world of travel with Expedia

Explore a world of travel with Expedia