Winter Holiday Rentals

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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Winter holiday rentals

Property grounds

Rustic campground in Butternut

Rustic campground in Butternut
Butternut
The price is HK$353
HK$537 total
includes taxes & fees
2 Jun - 3 Jun
Rustic campground in Butternut
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$1,227
HK$2,519 total
includes taxes & fees
3 Jun - 4 Jun
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
10.0 out of 10, Exceptional, (21 reviews)
"Great hosts and location. "
United States
Paul H.
The price is HK$980
HK$1,199 total
includes taxes & fees
2 Jun - 3 Jun
Discover Hawkins charm in our 3-bedroom retreat near ATV & 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, (15 reviews)
"Very clean. Beds were comfortable. The host was friendly. "
United States
Anne S.
The price is HK$980
HK$1,654 total
includes taxes & fees
30 Jun - 1 Jul
Charming 2-bedroom house located in Ojibwa WI just off the Tuscobia Trail.
Interior

Northwoods Escape: Lakeside Retreat w/ Deck

Northwoods Escape: Lakeside Retreat w/ Deck
3.0 star property
Stone Lake
The price is HK$2,398
HK$4,768 total
includes taxes & fees
2 Jun - 3 Jun
Northwoods Escape: Lakeside Retreat w/ Deck
WiFi, bed sheets

Chip-Wa Lodging Room 4

Chip-Wa Lodging Room 4
Hunter
The price is HK$901
HK$1,276 total
includes taxes & fees
7 Jun - 8 Jun
Chip-Wa Lodging Room 4
Interior

Lunar Lodge on Windfall Lake

Lunar Lodge on Windfall Lake
Exeland
The price is HK$1,239
HK$4,451 total
includes taxes & fees
2 Jun - 3 Jun
Lunar Lodge on Windfall Lake
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$2,516
HK$3,814 total
includes taxes & fees
9 Jun - 10 Jun
Renovated cabin on Lac Courte Oreilles Lake - minutes from trails!
Shower, hair dryer, towels, soap

Ultimate Hayward Trailhead Cabin

Ultimate Hayward Trailhead Cabin
Hayward
Ultimate Hayward Trailhead Cabin
Property grounds

Motorsports Basecamp near lakes and forest

Motorsports Basecamp near lakes and forest
Hayward
9.8 out of 10, Exceptional, (31 reviews)
"The place was clean and we enjoyed our stay. "
United States
Chris P.
The price is HK$983
HK$2,106 total
includes taxes & fees
2 Jun - 3 Jun
Motorsports Basecamp near lakes and forest
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$1,826 total
includes taxes & fees
8 Jun - 9 Jun
Red Pines - Elk Lake Efficiency #6A
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$1,153
HK$2,704 total
includes taxes & fees
3 Jun - 4 Jun
Cozy Lakefront Cabin, Dock + Trails : Trails Lodge
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, (32 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$2,116
HK$4,398 total
includes taxes & fees
7 Jun - 8 Jun
Lakefront Cabin w/ Pool Table+Waterfall: Northwoods Nostalgia + Modern Amenities
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$3,756
HK$4,705 total
includes taxes & fees
21 Jun - 22 Jun
15min to trailhead, King Bed, PacMan
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$2,735
HK$5,692 total
includes taxes & fees
9 Jun - 10 Jun
Lakefront Cabin on LCO - The Sunset Escape
TV, fireplace

Northwoods Escape: Lakeside Retreat w/ Deck

Northwoods Escape: Lakeside Retreat w/ Deck
Stone Lake
The price is HK$2,139
HK$4,875 total
includes taxes & fees
2 Jun - 3 Jun
Northwoods Escape: Lakeside Retreat w/ Deck
Exterior detail

Cozy Riverside Retreat | Sauna + Deck

Cozy Riverside Retreat | Sauna + 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$1,261
HK$3,146 total
includes taxes & fees
2 Jun - 3 Jun
Cozy Riverside Retreat | Sauna + Deck
Terrace/patio

Secluded Riverfront Cabin | Hot Tub + Starlink

Secluded Riverfront Cabin | Hot Tub + Starlink
Ojibwa
10.0 out of 10, Exceptional, (47 reviews)
"This cabin was a perfect fit for our family of five and our dog. Everything was clean and comfortable, and the hot tub was a highlight of our stay. The location made it easy to get on the snowmobile trails, and the hosts were wonderful to work with and very responsive."
United States
Jennifer P.
The price is HK$4,245
HK$5,115 total
includes taxes & fees
7 Jun - 8 Jun
Secluded Riverfront Cabin | Hot Tub + Starlink
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$1,873
HK$2,300 total
includes taxes & fees
27 Jun - 28 Jun
Lakefront cottage w/ convenient access to restaurants, atv and snowmobile trails
Terrace/patio

Dual Cabins-Hot Tub, 3 Kings, 2 Kitchens

Dual Cabins-Hot Tub, 3 Kings, 2 Kitchens
Hayward
9.8 out of 10, Exceptional, (18 reviews)
"Great property with every amenity needed."
United States
Mitchell D.
The price is HK$8,590
HK$10,744 total
includes taxes & fees
10 Jun - 11 Jun
Dual Cabins-Hot Tub, 3 Kings, 2 Kitchens
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

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

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

8/10 Good
"Was nice and clean, had a fresh look to it. Easy check in."
Nancy 2-night trip
Posted 7 hours ago
Lakefront cottage w/ convenient access to restaurants, atv and snowmobile trails

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 11 Expedia holiday rentals in Winter for a memorable holiday.

What can I see and do in Winter?

Perch Lake and Barker Lake are a couple of lovely local spots to get outside and enjoy nature. Chequamegon National Forest and Flambeau River 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.