Winter Holiday Rentals

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Holiday Rentals in Winter

5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.
10.0 out of 10, Exceptional, (67)
"Excellent vacation home with all the amenities you would ever need!"
United States
Laura K.
5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.
Telemark Northwoods Lodging
3.5 star property
9.0 out of 10, Wonderful, (316)
"Great room excellent people to worh with."
United States
Doyle
The price is AU$477
includes taxes & fees
27 Nov - 28 Nov
Telemark Northwoods Lodging
LCO Lakefront Cabin - Discounted for the Fall, Winter, & Spring
10.0 out of 10, Exceptional, (31)
"We love the cabin. Amenities are great. This was our 3rd visit. Fishing is always fun! "
United States
Linda F.
LCO Lakefront Cabin - Discounted for the Fall, Winter, & Spring
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!
9.6 out of 10, Exceptional, (208)
"Nice property in a great location. Problem is there was no air conditioning and with the extensive heat at the beginning of our stay and the bad air quality due to the Canadian fires we were not able to enjoy the cabin as we would have liked. We ended up leaving one night early. "
United States
Jim H.
Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!
Hayward, Round Lake Retreat! Private dock, 3 kayaks, beautifully maintained!
10.0 out of 10, Exceptional, (75)
"Loved our stay for Birkie weekend!"
United States
Christine S.
Hayward, Round Lake Retreat! Private dock, 3 kayaks, beautifully maintained!
Big Sisu - Newly Remodeled Nordic Hideaway on Silverthorn Lake
10.0 out of 10, Exceptional, (17)
"Wonderful stay - very peaceful. Terrific communication with the host. "
United States
Jason
Big Sisu - Newly Remodeled Nordic Hideaway on Silverthorn Lake
Breezy Bay Beach On Round Lake
10.0 out of 10, Exceptional, (61)
"Family of nine thoroughly enjoyed our stay. Great accommodations and beach. Paddle boat was a treat. Great location for fireworks."
United States
Dan W.
Breezy Bay Beach On Round Lake
1940’s Charming Vintage Cabin
10.0 out of 10, Exceptional, (8)
"Did some river kayaking in the area. Perfect place to stay."
United States
Daniel F.
1940’s Charming Vintage Cabin
Executive Custom Log Lodge on Little Round Lake
10.0 out of 10, Exceptional, (101)
"An excellent place for our family. We enjoyed the many areas for our family to play board games, card games and plenty of places for quiet time for our group. The extra fridge space was a luxury for our family meals. Our group enjoyed the outdoor decks and fire pit! Everything was as expected or better. "
United States
Steph L.
Executive Custom Log Lodge on Little Round Lake
Hayward Lakefront - Gorgeous Cabin, Four Seasons of Fun for up to 21 guests
9.6 out of 10, Exceptional, (78)
"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
Modern Cabin located between Grindstone and Lac Courte Oreilles
10.0 out of 10, Exceptional, (76)
"Wonderful and extremely clean cabin! It had everything we needed for a great stay!"
United States
Brian F.
Modern Cabin located between Grindstone and Lac Courte Oreilles
Big Chip - 1 is in the heart of the Chippewa Flowage 20 minutes from Hayward, WI
10.0 out of 10, Exceptional, (7)
"Had a great time! Beautiful property. Maybe a motion light on outside when returning late at night it was so dark. Otherwise everything was perfect"
United States
Melissa G.
Big Chip - 1 is in the heart of the Chippewa Flowage 20 minutes from Hayward, WI
Charming 5-bedroom cabin just outside Hayward near OO, Tiger Cat,and Spider Lake
2.0 star property
10.0 out of 10, Exceptional, (9)
"Simple Checkin, Responsive Host, Nice Location and property equipped to host 20+ person. Stayed 2 memorable and fun nights...."
United States
SANTHOSH KUMAR M.
Charming 5-bedroom cabin just outside Hayward near OO, Tiger Cat,and Spider Lake
Round Lake Cabin Retreat
9.4 out of 10, Exceptional, (72)
"Great weather. Layout of cabin was perfect for our group. Great time. Nice swimming area. Caught fish off the dock. Air conditioning would be nice but we totally had a great time."
United States
Brad B.
Round Lake Cabin Retreat
Cozy Cabin on Secluded Peninsula
9.8 out of 10, Exceptional, (48)
"Nice place quiet location"
United States
Jerad H.
Cozy Cabin on Secluded Peninsula
Northwoods Hayward Haven. Private 3 bedroom 3 bath, sleeps 8 very comfortably.
10.0 out of 10, Exceptional, (3)
"Beautiful, beautiful home! Absolutely everything was provided, other than food. Soft water in the house, great TVs and furniture. Very comfortable! Rent the boat or bring your own, as you need to get out on that clean, clear water! Deer came through the yard morning and night, eating up the acorns, otters playing in the water out on the lake. Dave had the firepit ready to go for us, as well as the sauna tent. It's located on a back bay, so nice and quiet. Close to town, but not too...
United States
Diane H.
Northwoods Hayward Haven. Private 3 bedroom 3 bath, sleeps 8 very comfortably.
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!"
United States
Bobbi B.
Lake House & Cottage-2 Docks, Firepits, Kitchens
Rustic and Charming one Bedroom cabin. Upgraded pontoon!
9.8 out of 10, Exceptional, (97)
"This was our 3rd stay! We love it. "
United States
Paulina L.
Rustic and Charming one Bedroom cabin. Upgraded pontoon!
The Sylvan Chalet, Modern, Lakefront, Private, Refined, Close to Trails,
10.0 out of 10, Exceptional, (3)
"Lovey stay in a cozy cabin. The views are wonderful and being surrounded by nature refreshing. "
United States
Marco O.
The Sylvan Chalet, Modern, Lakefront, Private, Refined, Close to Trails,
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

Find out more about Winter

Everything you need to know about Winter holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winter holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winter holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winter holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winter. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winter holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winter holiday rentals we have selected for you start as low as AU$477 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winter rentals

At Expedia, we put the best Winter holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winter rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winter holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winter. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 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.