A snowy landscape with a red barn and a red shed.

Winter Holiday Rentals

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Winter holiday rentals

Coffee/tea maker, fridge, microwave, oven

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

Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails.
Hawkins
10.0 out of 10, Exceptional, (23 reviews)
"Great hosts and location. "
United States
Paul H.
The price is HK$980
HK$1,199 total
includes taxes & fees
24 Jul - 25 Jul
Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails.
Property grounds

Red Pines - Elk Lake Efficiency #6A

Red Pines - Elk Lake Efficiency #6A
Phillips
9.6 out of 10, Exceptional, (12 reviews)
"Quiet, peaceful place that was perfect for a weekend getaway. The room was clean and well stocked. "
United States
Karan B.
The price is HK$1,096
HK$1,844 total
includes taxes & fees
18 Jul - 19 Jul
Red Pines - Elk Lake Efficiency #6A
Terrace/patio

Telemark Northwoods Lodging

Telemark Northwoods Lodging
3.5 star property
Cable
9.0 out of 10, Wonderful, (321 reviews)
"Great location for a fun Telemark event weekend."
United States
Ruth
The price is HK$1,340
HK$2,643 total
includes taxes & fees
12 Aug - 13 Aug
Telemark Northwoods Lodging
Property grounds

Rustic campground in Butternut

Rustic campground in Butternut
Butternut
The price is HK$353
HK$538 total
includes taxes & fees
28 Jul - 29 Jul
Rustic campground in Butternut
Exterior detail

Granny's Nest

Granny's Nest
Conrath
The price is HK$811
HK$1,435 total
includes taxes & fees
21 Jul - 22 Jul
Granny's Nest
WiFi, bed sheets

Chip-Wa Lodging Room 4

Chip-Wa Lodging Room 4
Hunter
10.0 out of 10, Exceptional, (1 review)
"Property exactly as described. Room was clean, comfortable and priced right. We will be back!"
United States
Sandra B.
The price is HK$901
HK$1,276 total
includes taxes & fees
28 Jul - 29 Jul
Chip-Wa Lodging Room 4
Smart TV

Cozy home in Wisconsin's recreational northwoods.

Cozy home in Wisconsin's recreational northwoods.
Butternut
8.0 out of 10, Very good, (4 reviews)
"Property was located just down the road from the snowmobiling trail and was easy and quick in/out access"
United States
Jake C.
The price is HK$862
HK$1,778 total
includes taxes & fees
14 Aug - 15 Aug
Cozy home in Wisconsin's recreational northwoods.
Property grounds

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

Lakefront cottage w/ convenient access to restaurants, atv and snowmobile trails
Phillips
9.6 out of 10, Exceptional, (31 reviews)
"Very nice place to stay!"
United States
Dina A.
The price is HK$1,686
HK$2,104 total
includes taxes & fees
25 Jul - 26 Jul
Lakefront cottage w/ convenient access to restaurants, atv and snowmobile trails
Living area

Lake Front Cabin, Media/Game Room, Kayaks, Multi-level deck--NEWLY REMODELED

Lake Front Cabin, Media/Game Room, Kayaks, Multi-level deck--NEWLY REMODELED
Hayward
10.0 out of 10, Exceptional, (14 reviews)
"Excellent property, exceptional hosts. "
United States
Michael H.
The price is HK$1,930
HK$3,838 total
includes taxes & fees
9 Aug - 10 Aug
Lake Front Cabin, Media/Game Room, Kayaks, Multi-level deck--NEWLY REMODELED
TV, fireplace

Northwoods Escape: Lakeside Retreat w/ Deck

Northwoods Escape: Lakeside Retreat w/ Deck
Stone Lake
10.0 out of 10, Exceptional, (3 reviews)
"We rented this property for our relatives visiting from Sweden. They were very happy with the accomadations."
United States
Jean C.
The price is HK$1,889
HK$4,581 total
includes taxes & fees
12 Aug - 13 Aug
Northwoods Escape: Lakeside Retreat w/ Deck
Smart TV, fireplace

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

Lakefront Cabin w/ Pool Table+Waterfall: Northwoods Nostalgia + Modern Amenities
Clam Lake
10.0 out of 10, Exceptional, (36 reviews)
"Stayed here for a snowmobile trip. Host helped us figure out the best way to access trails and was helpful with all questions we had. Very clean and easy to access place to stay with everything we were looking for!"
United States
Colten R.
The price is HK$2,783
HK$5,235 total
includes taxes & fees
9 Aug - 10 Aug
Lakefront Cabin w/ Pool Table+Waterfall: Northwoods Nostalgia + Modern Amenities
Property grounds

Lake Cabin · Hot Tub · Fire Pit · EV

Lake Cabin · Hot Tub · Fire Pit · EV
Hayward
9.8 out of 10, Exceptional, (22 reviews)
"Nice cabin, great beds. Really enjoyed our time. "
United States
Katie J.
The price is HK$8,229
HK$13,128 total
includes taxes & fees
28 Jul - 29 Jul
Lake Cabin · Hot Tub · Fire Pit · EV
Property grounds

15min to trailhead, King Bed, PacMan

15min to trailhead, King Bed, PacMan
Hayward
9.6 out of 10, Exceptional, (12 reviews)
"It was a good long weekend the stay was enjoyable with good neighbors and relaxing accommodations "
United States
Kevin K.
The price is HK$4,653
HK$5,825 total
includes taxes & fees
28 Jul - 29 Jul
15min to trailhead, King Bed, PacMan
Interior

Northwoods Escape: Lakeside Retreat w/ Deck

Northwoods Escape: Lakeside Retreat w/ Deck
3.0 star property
Stone Lake
The price is HK$2,328
HK$4,479 total
includes taxes & fees
9 Aug - 10 Aug
Northwoods Escape: Lakeside Retreat w/ Deck
WiFi, bed sheets

Chip-Wa Lodging Room 1

Chip-Wa Lodging Room 1
Hunter
10.0 out of 10, Exceptional, (3 reviews)
"Enjoyed our stay. Cozy and quaint."
United States
Thane B.
The price is HK$901
HK$1,276 total
includes taxes & fees
20 Jul - 21 Jul
Chip-Wa Lodging Room 1
WiFi, bed sheets

Chip-Wa Lodging Room 6

Chip-Wa Lodging Room 6
Hunter
10.0 out of 10, Exceptional, (1 review)
"Room was very clean. Property looks well kept and price was affordable."
United States
Kathy
The price is HK$901
HK$1,276 total
includes taxes & fees
21 Jul - 22 Jul
Chip-Wa Lodging Room 6
Terrace/patio

Secluded Riverfront Cabin | Hot Tub + Starlink

Secluded Riverfront Cabin | Hot Tub + Starlink
Ojibwa
10.0 out of 10, Exceptional, (47 reviews)
"We had such a good time! "
United States
Dan P.
The price is HK$5,223
HK$6,296 total
includes taxes & fees
27 Jul - 28 Jul
Secluded Riverfront Cabin | Hot Tub + Starlink
WiFi, bed sheets

Chip-Wa Lodging Room 5

Chip-Wa Lodging Room 5
Hunter
10.0 out of 10, Exceptional, (1 review)
"Place was defect for us. We are simple motel hotel people that want it clean, quiet, affordable. It was all of those things. And the owner was responsive and friendly and gave us the best recommendation for the perfect bar just around the corner. 😍"
United States
Heather
The price is HK$901
HK$1,276 total
includes taxes & fees
14 Aug - 15 Aug
Chip-Wa Lodging Room 5
Exterior detail

River's Edge Tiny Home | Expansive Deck

River's Edge Tiny Home | Expansive Deck
Park Falls
9.6 out of 10, Exceptional, (10 reviews)
"Stayed here for business trip. Much better than a hotel. Well kept property, nice outside spaces. "
United States
Dan O.
The price is HK$3,124
HK$5,420 total
includes taxes & fees
6 Aug - 7 Aug
River's Edge Tiny Home | Expansive Deck
TV, fireplace

Lakefront Cabin on LCO - The Sunset Escape

Lakefront Cabin on LCO - The Sunset Escape
Hayward
9.6 out of 10, Exceptional, (5 reviews)
"Very comfortable and great view of the lake."
United States
Jeffrey T.
The price is HK$3,742
HK$6,950 total
includes taxes & fees
13 Aug - 14 Aug
Lakefront Cabin on LCO - The Sunset Escape
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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Top Winter Hotel Reviews

Timber Inn

Timber Inn

10/10 Excellent
"Still in mid rehab. But even though there were esthetic icks , it didn’t not take away from the experience. Ive been coming here for years and I’m loving all the improvements!!"
Amy 2-night trip
Posted 19 hours ago
Timber Inn

Find out more about Winter

Search for holiday rentals in Winter on Expedia! You can easily find your home rentals, villas, holiday apartments in Winter using one of the methods below:

  • View our selection of featured holiday rentals in Winter
  • Use the map to find apartments and other holiday homes in the Winter neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winter while they last

Look no further and take a look at our great range of rental properties in Winter!

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?

5 bedroom 3- bath 8 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 Bears Den on the private lake as a favourite home for rent in Winter.

How many holiday rentals are there in Winter?

Choose from 12 Expedia holiday rentals in Winter for a memorable holiday.

What can I see and do in Winter?

Lake Winter and Perch Lake are a couple of lovely local spots to get outside and enjoy nature. Winter Town Hall 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.