Winter Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Winter holiday rentals

Interior

Fisher's Retreat: Hayward Home, Near ATV Trails!

Fisher's Retreat: Hayward Home, Near ATV Trails!
3.0 star property
Hayward
10.0 out of 10, Exceptional, (3 reviews)
"Great communication. Easy check in. Great location. Love the vintage vibe, home has clearly been well cared for. Would stay again. "
United States
Lisa
The price is HK$815
HK$2,637 total
includes taxes & fees
18 Apr - 19 Apr
Fisher's Retreat: Hayward Home, Near ATV Trails!
Interior

2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage

2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
Hayward
9.4 out of 10, Exceptional, (22 reviews)
"Cabin was clean. Everything 2 guys needed for a few days fishing."
United States
Tom N.
The price is HK$783
HK$1,072 total
includes taxes & fees
28 Apr - 29 Apr
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
Terrace/patio

Telemark Northwoods Lodging

Telemark Northwoods Lodging
3.5 star property
Cable
9.0 out of 10, Wonderful, (318 reviews)
"Beautiful setting, relaxing stay, comfortable and clean accommodations, super nice staff."
United States
Sarah
The price is HK$740
HK$1,986 total
includes taxes & fees
18 Apr - 19 Apr
Telemark Northwoods Lodging
Fridge, microwave, oven, stovetop

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
9.8 out of 10, Exceptional, (20 reviews)
"Great hosts and location. "
United States
Paul H.
The price is HK$979
HK$1,198 total
includes taxes & fees
17 Apr - 18 Apr
Discover Hawkins charm in our 3-bedroom retreat near ATV & Snowmobile Trails.
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, (28 reviews)
"Very nice place to stay!"
United States
Dina A.
The price is HK$909
HK$1,167 total
includes taxes & fees
18 Apr - 19 Apr
Lakefront cottage w/ convenient access to restaurants, atv and snowmobile trails
Interior

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

Charming 2-bedroom house located in Ojibwa WI just off the Tuscobia Trail.
Ojibwa
9.8 out of 10, Exceptional, (14 reviews)
"Very cozy, perfect for a family. Had everything we needed. "
United States
Erica C.
The price is HK$881
HK$1,525 total
includes taxes & fees
22 Apr - 23 Apr
Charming 2-bedroom house located in Ojibwa WI just off the Tuscobia Trail.
Exterior

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$1,079
HK$1,816 total
includes taxes & fees
18 Apr - 19 Apr
Red Pines - Elk Lake Efficiency #6A
Property grounds

Rustic campground in Butternut

Rustic campground in Butternut
Butternut
The price is HK$353
HK$537 total
includes taxes & fees
17 Apr - 18 Apr
Rustic campground in Butternut
Interior

Lunar Lodge on Windfall Lake

Lunar Lodge on Windfall Lake
Exeland
The price is HK$1,033
HK$3,762 total
includes taxes & fees
17 Apr - 18 Apr
Lunar Lodge on Windfall Lake
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$1,559
HK$4,214 total
includes taxes & fees
28 Apr - 29 Apr
Lakefront Cabin on LCO - The Sunset Escape
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$689
HK$1,612 total
includes taxes & fees
17 Apr - 18 Apr
Cozy home in Wisconsin's recreational northwoods.
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$900
HK$1,275 total
includes taxes & fees
17 Apr - 18 Apr
Chip-Wa Lodging Room 6
Outdoor dining

Cozy Lakefront Cabin, Dock + Trails : Trails Lodge

Cozy Lakefront Cabin, Dock + Trails : Trails Lodge
Cable
10.0 out of 10, Exceptional, (31 reviews)
"Everything was perfect! Very clean and cozy. We would definitely stay again."
United States
Kari G.
The price is HK$1,153
HK$2,721 total
includes taxes & fees
17 Apr - 18 Apr
Cozy Lakefront Cabin, Dock + Trails : Trails Lodge
Living area

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

Renovated cabin on Lac Courte Oreilles Lake - minutes from trails!
Northwoods Beach
10.0 out of 10, Exceptional, (24 reviews)
"Our second time staying and we love it! We especially enjoyed the addition of the front/lake facing deck "
United States
ANN M.
The price is HK$1,559
HK$2,711 total
includes taxes & fees
28 Apr - 29 Apr
Renovated cabin on Lac Courte Oreilles Lake - minutes from trails!
Interior

The Bunkhouse, cozy studio in adorable Ladysmith. Escape to the Northwoods!

The Bunkhouse, cozy studio in adorable Ladysmith. Escape to the Northwoods!
Ladysmith
10.0 out of 10, Exceptional, (1 review)
"Great place to stay at. Host was accommodating. It was clean and cozy. I would book again"
United States
Nathan H.
The price is HK$830
HK$1,041 total
includes taxes & fees
22 Apr - 23 Apr
The Bunkhouse, cozy studio in adorable Ladysmith. Escape to the Northwoods!
Interior

Northwoods Escape: Lakeside Retreat w/ Deck

Northwoods Escape: Lakeside Retreat w/ Deck
3.0 star property
Stone Lake
The price is HK$1,340
HK$3,651 total
includes taxes & fees
28 Apr - 29 Apr
Northwoods Escape: Lakeside Retreat w/ Deck
Property grounds

Time to Hideout in Hayward!

Time to Hideout in Hayward!
Hayward
The price is HK$1,058
HK$3,028 total
includes taxes & fees
19 Apr - 20 Apr
Time to Hideout in Hayward!
Interior

2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage

2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
Hayward
8.6 out of 10, Excellent, (9 reviews)
"Quiet resort. I really enjoyed spending time with my family and just getting away for a week."
United States
Shelli H.
The price is HK$783
HK$1,072 total
includes taxes & fees
19 Apr - 20 Apr
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
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, (9 reviews)
"Excellent property, exceptional hosts. "
United States
Michael H.
The price is HK$835
HK$2,467 total
includes taxes & fees
28 Apr - 29 Apr
Lake Front Cabin, Media/Game Room, Kayaks, Multi-level deck--NEWLY REMODELED
Exterior

2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage

2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
Hayward
8.4 out of 10, Very good, (18 reviews)
"Thank you for the great stay! I had everything I needed."
United States
Mark B.
The price is HK$979
HK$1,297 total
includes taxes & fees
19 Apr - 20 Apr
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winter Hotel Reviews

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

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

10/10 Excellent
"This Cabin was incredible!! Everything you need... towels, soaps, blow dryer, extra bedding and pillows, cleaning supplies, laundry soaps, even seasonings and coffee pods. It has kayaks, life jackets, games books, great wifi service, pool table!! The setting was beautiful!! Nice dock area and a bridge over a cascade waterfall! The hosts were also awesome!! Nicest place I have ever stayed!!!"
Diane A. 5-night trip
Posted 11 days ago
Lakefront Cabin w/ Pool Table+Waterfall: Northwoods Nostalgia + Modern Amenities

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?

Amazing Sunsets, Peaceful, Well Maintained Lake home on Beautiful, Barker lake: This highly rated holiday home rental in Winter is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 Black Dan Lake 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.