Winter Holiday Rentals

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Check prices for these dates

In two weeks
5 Dec - 7 Dec
In two months
16 Jan - 18 Jan
In three months
13 Feb - 15 Feb
In four months
13 Mar - 15 Mar

Holiday Rentals in Winter

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

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

Winter
10.0 out of 10, Exceptional, (68)
"This was our third year staying at this property and every year keeps getting better and better! Our kids love it here and so do the adults. The firepit and screened in porch were enjoyed the most. "
United States
Luke C.
5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.
Property grounds
Hayward, Round Lake Retreat! Private dock, 3 kayaks, beautifully maintained!

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

Hayward
10.0 out of 10, Exceptional, (75)
"It was very relaxed, peaceful and easy to find. "
United States
Christine V.
Hayward, Round Lake Retreat! Private dock, 3 kayaks, beautifully maintained!
Dining
Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!

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

Hayward
9.6 out of 10, Exceptional, (211)
"By far the best cabin we’ve stayed in - very clean, necessities stocked, perfect view and access to the lake. Woke to the song of the loons, watched the eagles fish and the otters swim from the porch. Oh and the fishing wasn’t bad either! Highly recommend if you are looking for a relaxing vacation. A big thanks to hosts for sharing a little piece of paradise."
United States
Atsuko T.
Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!
Outdoor dining
Modern Cabin located between Grindstone and Lac Courte Oreilles

Modern Cabin located between Grindstone and Lac Courte Oreilles

Northwoods Beach
10.0 out of 10, Exceptional, (76)
"Very nice cabin. Extremely quiet and peaceful. Great place to sit out by the camp fire and relax."
United States
Tom H.
Modern Cabin located between Grindstone and Lac Courte Oreilles
Terrace/patio
Telemark Northwoods Lodging

Telemark Northwoods Lodging

3.5 star property
Cable
9.0 out of 10, Wonderful, (316)
"Colors of the trees were beautiful, staff helpful, trails plentiful and walkable."
United States
Kenneth
The price is HK$1,149
HK$2,425 total
includes taxes & fees
27 Nov - 28 Nov
Telemark Northwoods Lodging
Fridge, microwave, oven, stovetop
Beautiful Ponderosa Pine Log Cabin - Northwoods Retreat On 10 Acres

Beautiful Ponderosa Pine Log Cabin - Northwoods Retreat On 10 Acres

Ladysmith
10.0 out of 10, Exceptional, (267)
"Great communication and such a cozy place to stay!"
United States
Caitlyn
Beautiful Ponderosa Pine Log Cabin - Northwoods Retreat On 10 Acres
Bar (on property)
Executive Custom Log Lodge on Little Round Lake

Executive Custom Log Lodge on Little Round Lake

Hayward
10.0 out of 10, Exceptional, (102)
"Lovely home, spotless, perfect location, well-stocked kitchen, close to Hayward and golf, What’s not to love for a family vacation? "
United States
Linda J.
Executive Custom Log Lodge on Little Round Lake
Property grounds
LCO Lakefront Cabin - Discounted for the Fall, Winter, & Spring

LCO Lakefront Cabin - Discounted for the Fall, Winter, & Spring

Northwoods Beach
10.0 out of 10, Exceptional, (32)
"The cabin was perfect. One of the best weeks of the year! "
United States
Casie M.
LCO Lakefront Cabin - Discounted for the Fall, Winter, & Spring
Dining
Grand View Lodge -New Listing With Room For The Family

Grand View Lodge -New Listing With Room For The Family

Hayward
9.4 out of 10, Exceptional, (11)
"Over all it was a very nice stay the lake was a little over run with weeds but we enjoyed none the less!"
United States
Allan J.
Grand View Lodge -New Listing With Room For The Family
Exterior
Big Sisu - Newly Remodeled Nordic Hideaway on Silverthorn Lake

Big Sisu - Newly Remodeled Nordic Hideaway on Silverthorn Lake

Hayward
10.0 out of 10, Exceptional, (18)
"Beautiful and peaceful property to connect with loved ones and play with our grandchildren on the lake. "
United States
Michelle A.
Big Sisu - Newly Remodeled Nordic Hideaway on Silverthorn Lake
Interior
Hayward Lakefront - Gorgeous Cabin, Four Seasons of Fun for up to 21 guests

Hayward Lakefront - Gorgeous Cabin, Four Seasons of Fun for up to 21 guests

Hayward
9.6 out of 10, Exceptional, (79)
"Great location, lots of room, and cute cabins."
United States
Stephanie C.
Hayward Lakefront - Gorgeous Cabin, Four Seasons of Fun for up to 21 guests
Outdoor dining
Northwoods Hayward Haven. Private 3 bedroom 3 bath, sleeps 8 very comfortably.

Northwoods Hayward Haven. Private 3 bedroom 3 bath, sleeps 8 very comfortably.

Hayward
10.0 out of 10, Exceptional, (3)
"Dave was an amazing host, he had the property setup for us. Had a ton of little xtras and everything labeled and easy to understand and use. "
United States
Jeff H.
Northwoods Hayward Haven. Private 3 bedroom 3 bath, sleeps 8 very comfortably.
Interior
Cozy Cabin on Secluded Peninsula

Cozy Cabin on Secluded Peninsula

Hayward
9.8 out of 10, Exceptional, (48)
"We were in the area for a family reunion. The location was great. "
United States
Katie V.
Cozy Cabin on Secluded Peninsula
Interior
Updated, Tranquil Retreat on Round Lake - 3 Bed, 3 Bath with Sleeping Loft

Updated, Tranquil Retreat on Round Lake - 3 Bed, 3 Bath with Sleeping Loft

Hayward
10.0 out of 10, Exceptional, (10)
"Beautiful views, great location!"
United States
Aaron A.
Updated, Tranquil Retreat on Round Lake - 3 Bed, 3 Bath with Sleeping Loft
Smart TV, fireplace, books
Modern Cabin with Classic Northwoods Experience...Close to Trails

Modern Cabin with Classic Northwoods Experience...Close to Trails

Hayward
10.0 out of 10, Exceptional, (35)
"Excellent cabin!"
United States
Eric J.
Modern Cabin with Classic Northwoods Experience...Close to Trails
Interior
Sandalwood Retreat on Round Lake - Waterfront property with screened porch 

Sandalwood Retreat on Round Lake - Waterfront property with screened porch 

Hayward
10.0 out of 10, Exceptional, (41)
"Our family has been coming up to the northern woods for the past 35 years. We enjoy renting houses on different lakes. SandalWood and Round Lake are by far the best! We would love to stay there again!"
United States
Bill J.
Sandalwood Retreat on Round Lake - Waterfront property with screened porch 
Terrace/patio
Lake House & Cottage-2 Docks, Firepits, Kitchens

Lake House & Cottage-2 Docks, Firepits, Kitchens

Hayward
9.8 out of 10, Exceptional, (18)
"The house was perfect for a weekend get away up north!"
United States
Bobbi B.
Lake House & Cottage-2 Docks, Firepits, Kitchens
Exterior
Charming 5-bedroom cabin just outside Hayward near OO, Tiger Cat,and Spider Lake

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

2.0 star property
Hayward
10.0 out of 10, Exceptional, (9)
"Thanks for a wonderful stay! "
United States
Daniel K.
Charming 5-bedroom cabin just outside Hayward near OO, Tiger Cat,and Spider Lake
Smart TV, fireplace, DVD player
Rustic and Charming one Bedroom cabin. Upgraded pontoon!

Rustic and Charming one Bedroom cabin. Upgraded pontoon!

Hayward
9.8 out of 10, Exceptional, (97)
"Had a wonderful time in this wonderful cabin! Would stay again!"
United States
Nikki V.
Rustic and Charming one Bedroom cabin. Upgraded pontoon!
Smart TV, fireplace, DVD player, books
Breezy Bay Beach On Round Lake

Breezy Bay Beach On Round Lake

Hayward
10.0 out of 10, Exceptional, (62)
"We had a week stay with our family at this place and it was perfect! "
United States
Kelli C.
Breezy Bay Beach On Round Lake
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

Breezy Bay Beach On Round Lake

Breezy Bay Beach On Round Lake

10/10 Excellent
"Great property perfect for families"
Mary C. 3-night trip
Posted 4 days ago
Breezy Bay Beach On Round Lake

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.

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. Fishtrap Lake and Chequamegon National Forest 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.