Winter Holiday Rentals

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Holiday Rentals in Winter

Spacious Winter Retreat w/ River Access + Kayaks!
TV, fireplace, DVD player, table football
Spacious Winter Retreat w/ River Access + Kayaks!
9.0 out of 10, Wonderful, (17)
"This has been the second year we’ve been here. It’s a great place for a large group with plenty of space for everyone! This will continue to be our go to spot for years to come! "
Spacious Winter Retreat w/ River Access + Kayaks!
Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin
Exterior
Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin
8.8 out of 10, Excellent, (16)
"Newer owner is showing improvement to property."
Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin
Bears Den on the private lake
Interior
Bears Den on the private lake
9.6 out of 10, Exceptional, (26)
"The lake was great and the living situation for our large group was very comfortable. The only reason I give it 4 stars is because there was no hot water. The showers were absolutely freezing. Besides that everything was great."
Bears Den on the private lake
Telemark Northwoods Lodging
Deluxe Suite, 1 Bedroom, Kitchen | Terrace/patio
Telemark Northwoods Lodging
3.5 star property
9.0 out of 10, Wonderful, (256)
"Very clean and very comfortable "
The price is AU$209
includes taxes & fees
24 Nov - 25 Nov
Telemark Northwoods Lodging
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, (182)
"We decided last minute to get away for a quick, midweek relaxation trip. We now wish we’d booked this cabin for a week! Check-in was a breeze, the cabin was spotless, and the western facing view of the lake was gorgeous at every hour of the day. The cabin is set back on a picturesque, tree-framed road with little to no traffic. We enjoyed morning walks with our coffee, and late nights around the campfire with our cocktails. (All firewood was provided!) We just can’t say enough great things...
Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!
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, (241)
"We had a wonderful weekend relaxing in the cabin. Lots of time spent laughing, soaking in the hot tub, and playing games or painting inside while it rained. We would definitely come back."
Beautiful Ponderosa Pine Log Cabin - Northwoods Retreat On 10 Acres
Northwoods multiple family size cabin. ATV/UTV, snowmobile trail access and lake
Property grounds
Northwoods multiple family size cabin. ATV/UTV, snowmobile trail access and lake
9.6 out of 10, Exceptional, (25)
"We had a lovely and cozy stay! The backyard was just amazing and peaceful...had everything we could want. Only downfall was the mattresses in the bunkroom....very uncomfortable and one of the beds broke. Otherwise, a super place!"
Northwoods multiple family size cabin. ATV/UTV, snowmobile trail access and lake
Newly Built Trailside Chalet in The Brook - direct access to CAMBA/Birkie Trails
Exterior
Newly Built Trailside Chalet in The Brook - direct access to CAMBA/Birkie Trails
10.0 out of 10, Exceptional, (72)
"This was a perfect getaway. Near Hayward if you need anything, but still tucked away and secluded with access to trails. Very comfortable and clean."
The price is AU$442
includes taxes & fees
25 Nov - 26 Nov
Newly Built Trailside Chalet in The Brook - direct access to CAMBA/Birkie Trails
Round Lake Cabin Retreat
TV, fireplace, DVD player, books
Round Lake Cabin Retreat
9.4 out of 10, Exceptional, (63)
"no tv,one in basement nothing to hook up to.On crappy days and nights would of been useful'."
Round Lake Cabin Retreat
Peaceful cabin on the Flambeau River
Property grounds
Peaceful cabin on the Flambeau River
10.0 out of 10, Exceptional, (118)
"My family of 6 adults and 2 children stayed in Shannon’s cabin for a week for a family wedding and loved the location and space. The cabin is tucked back into the woods and on the river and very beautiful! Shannon was a great host and very helpful for accommodations. "
Peaceful cabin on the Flambeau River
Lakefront Wisconsin Cabin with Boat Dock!
TV, fireplace, DVD player
Lakefront Wisconsin Cabin with Boat Dock!
9.6 out of 10, Exceptional, (67)
"Very quiet and comfortable place to stay. I would like to return with friends to fish. The availability of renting the pontoon was fantastic. The whole family enjoyed our stay "
Lakefront Wisconsin Cabin with Boat Dock!
Pet-Friendly Lakeside Chalet w/ Kayaks and Canoe!
Interior
Pet-Friendly Lakeside Chalet w/ Kayaks and Canoe!
10.0 out of 10, Exceptional, (91)
"Our group of 9 friends had the best time at the Cattail Chalet. The space was beautiful, new & very clean. We fit comfortably & had lots a sleeping options. The big windows & view of the lake were spectacular. We saw lots of wildlife, including swans & playful little otter. The welcome binder was filled with thorough instructions for the house & helpful suggestions for the area. Brad was very responsive to all communication. We would definitely rent this space again."
Pet-Friendly Lakeside Chalet w/ Kayaks and Canoe!
Pet-Friendly Lakeside Cabin with Kayaks and Canoe!
Property grounds
Pet-Friendly Lakeside Cabin with Kayaks and Canoe!
10.0 out of 10, Exceptional, (116)
"My husband, two sons (16 and 18) our dog and I spent two nights at this gem. Our sons arrived about a half a hour before we did as we picked up groceries in Hayward (about 20 minutes away). They had already started playing ping pong before we arrived. Once we arrived, the canoe and kayaks were put in the water and were used the rest of our trip. We caught bass, bluegills and northerns and enjoyed the fall colors that surrounded the grounds. The setting is quite private, located at the end of a...
Pet-Friendly Lakeside Cabin with Kayaks and Canoe!
Lake Hayward. Private Lakefront Within Walking Distance To Downtown Hayward
Lake
Lake Hayward. Private Lakefront Within Walking Distance To Downtown Hayward
9.8 out of 10, Exceptional, (106)
"Overall it was a nice stay ,we were out exploring things so we were not at the house alot but when we were there it was comfortable. It had everything we needed for our stay there I wish the weather would’ve been warmer so we could experience the lake a little bit more, but it was still a nice stay"
Lake Hayward. Private Lakefront Within Walking Distance To Downtown Hayward
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
Interior
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
9.6 out of 10, Exceptional, (19)
"My stay in cabin 2 was great. Spent our time fishing and exploring the area. Be aware the water level is low this time of year. I would recommend this resort to a friend. "
The price is AU$166
includes taxes & fees
30 Nov - 1 Dec
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage
Hayward, Round Lake Retreat. 4 Season
Exterior
Hayward, Round Lake Retreat. 4 Season
10.0 out of 10, Exceptional, (53)
"2nd time at this property, and love how well appointed, stocked and furnished it is. There hasn’t been a single thing I needed in the kitchen that wasn’t available. Comfortable beds, cozy and clean. "
Hayward, Round Lake Retreat. 4 Season
Secluded River Retreat w/Hot Tub, WIFI, King Beds
Exterior
Secluded River Retreat w/Hot Tub, WIFI, King Beds
10.0 out of 10, Exceptional, (39)
"We booked this for a little family week getaway, it checked all of our boxes. Close to water, secluded, cozy, the hot tub, and enough space for all of us! The hosts are amazing and very communicative before and during your stay if you have any questions or feedback! We brought a couple extra kayaks, and used the ones on the property. There is a launch just up the road that gives you about 30 minutes, and another just a bit further that was just over an hour. The fire pit near the water was...
The price is AU$725
includes taxes & fees
4 Dec - 5 Dec
Secluded River Retreat w/Hot Tub, WIFI, King Beds
North Fork Flambeau River near Park Falls, 3BR, 1BA country home, on ATV route.
Interior
North Fork Flambeau River near Park Falls, 3BR, 1BA country home, on ATV route.
9.6 out of 10, Exceptional, (11)
"This was a nice location with a great view "
North Fork Flambeau River near Park Falls, 3BR, 1BA country home, on ATV route.
Charming Log Cabin with Wood Burning Fireplace – 1 mile from Downtown Hayward
Property grounds
Charming Log Cabin with Wood Burning Fireplace – 1 mile from Downtown Hayward
10.0 out of 10, Exceptional, (120)
"We came to Hayward for a long weekend to fish. The cabin was awesome. Clean and very well kept. Cozy but spacious. Quiet neighborhood too and plenty of deer sightings."
Charming Log Cabin with Wood Burning Fireplace – 1 mile from Downtown Hayward
6 Miles to Downtown Hayward! Full Recreation 500 Acre Lake; Quintessential Cabin
Property grounds
6 Miles to Downtown Hayward! Full Recreation 500 Acre Lake; Quintessential Cabin
9.8 out of 10, Exceptional, (54)
"Everything about the stay was consistent with the description and there were no surprises. Nice quiet lake perfect for relaxing on a pontoon boat. Cabin was comfortable and looked exactly like the photos."
6 Miles to Downtown Hayward! Full Recreation 500 Acre Lake; Quintessential Cabin
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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Other types of properties in Winter you may be interested in

Spacious Winter Retreat w/ River Access + Kayaks!
TV, fireplace, DVD player, table football
Spacious Winter Retreat w/ River Access + Kayaks!
9.0 out of 10, Wonderful, (17)
"This has been the second year we’ve been here. It’s a great place for a large group with plenty of space for everyone! This will continue to be our go to spot for years to come! "
Spacious Winter Retreat w/ River Access + Kayaks!
Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin
Exterior
Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin
8.8 out of 10, Excellent, (16)
"Newer owner is showing improvement to property."
Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin
Bears Den on the private lake
Interior
Bears Den on the private lake
9.6 out of 10, Exceptional, (26)
"The lake was great and the living situation for our large group was very comfortable. The only reason I give it 4 stars is because there was no hot water. The showers were absolutely freezing. Besides that everything was great."
Bears Den on the private 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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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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?

Spacious Winter Retreat w/ River Access + Kayaks!: This highly rated holiday home rental in Winter offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 7 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 Bears Den on the private lake as a favourite home for rent in Winter.

How many holiday rentals are there in Winter?

Choose from 14 Expedia holiday rentals in Winter for a memorable holiday.

What can I see and do in Winter?

Lake Winter and Ojibwa State Park are a couple of lovely local spots to get outside and enjoy nature. Barber Lake 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.