Winter Holiday Rentals

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Check prices for these dates

In two weeks
24 Oct - 26 Oct
In one month
7 Nov - 9 Nov
In two months
5 Dec - 7 Dec
In three months
2 Jan - 4 Jan

Holiday Rentals in Winter

Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin
Exterior

Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

8.4 out of 10, Very good, (27)
"Everyone was polite and very according definitely going again this summer"
Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin
5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.
Property grounds

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

10.0 out of 10, Exceptional, (65)
"Everything you need and more for all ages"
5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.
Amazing Sunsets, Peaceful, Well Maintained Lake home on Beautiful, Barker lake
Outdoor dining

Amazing Sunsets, Peaceful, Well Maintained Lake home on Beautiful, Barker lake

9.8 out of 10, Exceptional, (59)
"Nice place! We had a wonderful experience, would definitely come back some day!"
Amazing Sunsets, Peaceful, Well Maintained Lake home on Beautiful, Barker lake
Telemark Northwoods Lodging
Terrace/patio

Telemark Northwoods Lodging

3.5 star property
9.0 out of 10, Wonderful, (309)
"Perfect lodging option in a wonderful location."
The price is HK$1,149
HK$1,258 total
includes taxes & fees
8 Oct - 9 Oct
Telemark Northwoods Lodging
A-frame Cabin w/ Private Boat Dock!
Interior

A-frame Cabin w/ Private Boat Dock!

3.0 star property
A-frame Cabin w/ Private Boat Dock!
Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!
Dining

Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!

9.6 out of 10, Exceptional, (204)
"Clean, had all the things for a comfortable stay. "
The price is HK$1,044
HK$2,645 total
includes taxes & fees
8 Oct - 9 Oct
Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!
Hayward, Round Lake Retreat! Private dock, 3 kayaks, beautifully maintained!
Property grounds

Hayward, Round Lake Retreat! Private dock, 3 kayaks, beautifully maintained!

10.0 out of 10, Exceptional, (72)
"Loved our stay for Birkie weekend!"
Hayward, Round Lake Retreat! Private dock, 3 kayaks, beautifully maintained!
Round Lake Cabin Retreat
TV, fireplace, DVD player, books

Round Lake Cabin Retreat

9.4 out of 10, Exceptional, (72)
"Loves the location and beautiful Round Lake! Our family could all be together and relax with plenty of space!"
Round Lake Cabin Retreat
Executive Custom Log Lodge on Little Round Lake
Bar (on property)

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

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

9.8 out of 10, Exceptional, (62)
"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
Beautiful Ponderosa Pine Log Cabin - Northwoods Retreat On 10 Acres
Fridge, microwave, oven, stovetop

Beautiful Ponderosa Pine Log Cabin - Northwoods Retreat On 10 Acres

10.0 out of 10, Exceptional, (260)
"we enjoyed our 3 night stay hot tube was nice was a chilly rainy snowy weekend fireplace was awesome to sit around stay warm would go back and stay again "
Beautiful Ponderosa Pine Log Cabin - Northwoods Retreat On 10 Acres
Charming 5-bedroom cabin just outside Hayward near OO, Tiger Cat,and Spider Lake
Exterior

Charming 5-bedroom cabin just outside Hayward near OO, Tiger Cat,and Spider Lake

2.0 star property
10.0 out of 10, Exceptional, (8)
"Simple Checkin, Responsive Host, Nice Location and property equipped to host 20+ person. Stayed 2 memorable and fun nights...."
Charming 5-bedroom cabin just outside Hayward near OO, Tiger Cat,and Spider Lake
Modern Cabin located between Grindstone and Lac Courte Oreilles
Outdoor dining

Modern Cabin located between Grindstone and Lac Courte Oreilles

10.0 out of 10, Exceptional, (74)
"The screened porch was amazing"
Modern Cabin located between Grindstone and Lac Courte Oreilles
Lake Hayward. Private Lakefront Within Walking Distance To Downtown Hayward
Dining

Lake Hayward. Private Lakefront Within Walking Distance To Downtown Hayward

9.8 out of 10, Exceptional, (113)
"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
Grand View Lodge -New Listing With Room For The Family
Dining

Grand View Lodge -New Listing With Room For The Family

9.2 out of 10, Wonderful, (9)
"Over all it was a very nice stay the lake was a little over run with weeds but we enjoyed none the less!"
Grand View Lodge -New Listing With Room For The Family
Breezy Bay Beach On Round Lake
Smart TV, fireplace, DVD player, books

Breezy Bay Beach On Round Lake

10.0 out of 10, Exceptional, (60)
"We had a week stay with our family at this place and it was perfect! "
Breezy Bay Beach On Round Lake
Cozy Cabin on Secluded Peninsula
Interior

Cozy Cabin on Secluded Peninsula

9.8 out of 10, Exceptional, (45)
"Beautiful location. Excellent communication. Thanks for a great week. "
Cozy Cabin on Secluded Peninsula
Charming 2-bedroom Hayward Cabin on Lac Courte Oreilles
Smart TV, fireplace

Charming 2-bedroom Hayward Cabin on Lac Courte Oreilles

10.0 out of 10, Exceptional, (18)
"Exactly as described, wonderful lake/ cabin get away. Beautiful swimming area for children."
Charming 2-bedroom Hayward Cabin on Lac Courte Oreilles
Moose Lake Hayward WI
Terrace/patio

Moose Lake Hayward WI

2.0 star property
9.8 out of 10, Exceptional, (10)
"Our first time staying here. Perfect cabin for our weekend of fishing. Wish we had booked a couple more days. Walleye fishing was excellent. We will be back."
Moose Lake Hayward WI
Lake House & Cottage-2 Docks, Firepits, Kitchens
Terrace/patio

Lake House & Cottage-2 Docks, Firepits, Kitchens

9.8 out of 10, Exceptional, (18)
"The house was perfect for a weekend get away up north!"
Lake House & Cottage-2 Docks, Firepits, 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

Telemark Northwoods Lodging

Telemark Northwoods Lodging

10/10 Excellent
"A little outdated, but it did the job and was comfortable and clean. Loved the biking!"
Ricky 1-night trip
Posted 4 days ago
Telemark Northwoods Lodging

Find out more about Winter

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!

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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 Amazing Sunsets, Peaceful, Well Maintained Lake home on Beautiful, Barker lake as a favourite home for rent in Winter.

How many holiday rentals are there in Winter?

Choose from 13 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. 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.