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
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Winter holiday rentals

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
26 Jul - 27 Jul
Chip-Wa Lodging Room 4
Interior

Lunar Lodge on Windfall Lake

Lunar Lodge on Windfall Lake
Exeland
The price is HK$1,410
HK$4,649 total
includes taxes & fees
26 Jul - 27 Jul
Lunar Lodge on Windfall Lake
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, (24 reviews)
"Great hosts and location. "
United States
Paul H.
The price is HK$980
HK$1,200 total
includes taxes & fees
31 Jul - 1 Aug
Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails.
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$5,008
HK$6,036 total
includes taxes & fees
26 Jul - 27 Jul
Secluded Riverfront Cabin | Hot Tub + Starlink
Property grounds

Rustic campground in Butternut

Rustic campground in Butternut
Butternut
The price is HK$353
HK$538 total
includes taxes & fees
25 Jul - 26 Jul
Rustic campground in Butternut
Property grounds

Motorsports Basecamp near lakes and forest

Motorsports Basecamp near lakes and forest
Hayward
9.8 out of 10, Exceptional, (32 reviews)
"The place was clean and we enjoyed our stay. "
United States
Chris P.
The price is HK$1,662
HK$2,961 total
includes taxes & fees
28 Jul - 29 Jul
Motorsports Basecamp near lakes and forest
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
30 Jul - 31 Jul
Chip-Wa Lodging Room 5
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$1,341
HK$2,644 total
includes taxes & fees
27 Jul - 28 Jul
Telemark Northwoods Lodging
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$1,949
HK$3,860 total
includes taxes & fees
9 Aug - 10 Aug
Lake Front Cabin, Media/Game Room, Kayaks, Multi-level deck--NEWLY REMODELED
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
8 Aug - 9 Aug
Chip-Wa Lodging Room 6
Property grounds

Red Pines - Elk Lake Efficiency #6A

Red Pines - Elk Lake Efficiency #6A
Phillips
9.6 out of 10, Exceptional, (13 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$1,802 total
includes taxes & fees
24 Aug - 25 Aug
Red Pines - Elk Lake Efficiency #6A
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
6 Aug - 7 Aug
Chip-Wa Lodging Room 1
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$863
HK$1,820 total
includes taxes & fees
3 Aug - 4 Aug
Cozy home in Wisconsin's recreational northwoods.
WiFi, bed sheets

Chip-Wa Lodging Room 2

Chip-Wa Lodging Room 2
Hunter
8.0 out of 10, Very good, (2 reviews)
"Excellent for a short fishing trip or short stay! Smaller rooms without all the frills. Very clean and easy process to check in and out. Cost was acceptable for the value. If you are looking for a basic stay this is it. Excellent value and location for anyone who’s experiencing the outdoors of the Northwoods. "
United States
Matthew
The price is HK$901
HK$1,276 total
includes taxes & fees
28 Jul - 29 Jul
Chip-Wa Lodging Room 2
Exterior detail

River's Edge Tiny Home | Expansive Deck

River's Edge Tiny Home | Expansive Deck
Park Falls
9.8 out of 10, Exceptional, (11 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$1,855
HK$3,886 total
includes taxes & fees
6 Aug - 7 Aug
River's Edge Tiny Home | Expansive Deck
Interior

Chip-Wa Lodging Room 3

Chip-Wa Lodging Room 3
Hunter
8.0 out of 10, Very good, (1 review)
The price is HK$901
HK$1,276 total
includes taxes & fees
28 Jul - 29 Jul
Chip-Wa Lodging Room 3
Exterior detail

Granny's Nest

Granny's Nest
Conrath
The price is HK$812
HK$1,435 total
includes taxes & fees
29 Jul - 30 Jul
Granny's Nest
Outdoor dining

Cozy Lakefront Cabin, Dock + Trails : Trails Lodge

Cozy Lakefront Cabin, Dock + Trails : Trails Lodge
Cable
10.0 out of 10, Exceptional, (32 reviews)
"Great cabin! Very enjoyable stay and excellent communication. Thank you!"
United States
Edward E.
The price is HK$2,111
HK$3,866 total
includes taxes & fees
22 Aug - 23 Aug
Cozy Lakefront Cabin, Dock + Trails : Trails Lodge
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$1,568
HK$1,966 total
includes taxes & fees
24 Aug - 25 Aug
Lakefront cottage w/ convenient access to restaurants, atv and snowmobile trails
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$3,929
HK$7,182 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
"I'll be back Thank you Great location The brown comforter is the one lol"
Rick 1-night trip
Posted 4 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.