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Winter Vacation Rentals

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Vacation Rentals in Winter

North Wisconsin Private Island Vacation Home!!

North Wisconsin Private Island Vacation Home!!

Winter, WI

Situated on the waterfront, this vacation home is 6.9 mi (11.1 km) from Chequamegon National Forest and 11.6 mi (18.7 km) from Lake Chippewa. Callahan Lake and ...

4.9/5Exceptional! (22 reviews)
Wonderful, relaxing stay.

"What a great place, we didn't want to leave and are already planning to come back. Agree with a few other reviews - clearing out some of the underbrush would provide better views of the water. And if you enjoy cooking like we do, the kitchen is sorely lacking in bakeware. We made do. Had an absolutely ..."…"

Reviewed on Oct 11, 2020

North Wisconsin Private Island Vacation Home!!
Beautiful 3 Bedroom Lake Home Near Winter, Wisconsin

Beautiful 3 Bedroom Lake Home Near Winter, Wisconsin

Winter, WI

Located on the waterfront, this family-friendly vacation home is 3.3 mi (5.3 km) from Chequamegon National Forest and 11.1 mi (17.8 km) from Lake Chippewa. Callahan ...

4.9/5Exceptional! (7 reviews)
Amazing Fall Trip

"My wife and I had to make some last minute changes to our fall trip, this place was available, so we gave it a try. We are so glad that we did. Christine was so great to work with, if we needed something she was quick to respond. The place was very nice and you can tell that they are in the middle ..."…"

Reviewed on Oct 16, 2020

Beautiful 3 Bedroom Lake Home Near Winter, Wisconsin
Bears Den on Private Lake

Bears Den on Private Lake

Winter, WI

Located on the waterfront, this family-friendly vacation home is 0.1 mi (0.1 km) from Chequamegon National Forest and 10.3 mi (16.6 km) from Lake Chippewa. Callahan ...

4.6/5Exceptional! (13 reviews)
Great

"Clean, comfy beds, and nice deck. Mosquitoes were thick everywhere up here. Great time!"…"

Reviewed on Sep 7, 2020

Bears Den on Private Lake
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Summer in Winter

Summer in Winter

Winter, WI

Situated on the waterfront, this cabin is 2.1 mi (3.4 km) from Chequamegon National Forest and 10.9 mi (17.6 km) from Lake Chippewa. Callahan Lake and Round ...

4.8/5Exceptional! (62 reviews)
Family vacation

"Great rental with a gorgeous view. Close Atv trails, fun water activities, and fishing. Cabin had lots of movies to watch. Good place to reconnect with the family."…"

Reviewed on Oct 20, 2020

Summer in Winter
Summer in Winter

Summer in Winter

Winter, WI

Situated in Winter, this golf cabin is 2.1 mi (3.4 km) from Chequamegon National Forest and 10.9 mi (17.6 km) from Lake Chippewa. Callahan Lake and Round Lake ...

4.7/5Exceptional! (53 reviews)
Recharged!

"We had a wonderful 6 days of nothing peace and quiet. The little cabin was just right. It was clean and comfortable. The bed was perfect for us to sleep in. It does really have everything you would need- besides your food, drink and clothing. We way overpacked. Our dogs enjoyed their stay as well. ..."…"

Reviewed on Nov 3, 2020

Summer in Winter
Amazing Sunsets, Peaceful, Well Maintained Lake Home on Beautiful, Barker Lake

Amazing Sunsets, Peaceful, Well Maintained Lake Home on Beautiful, Barker Lake

Winter, WI

Situated on the beach, this vacation home is 0.1 mi (0.1 km) from Chequamegon National Forest and 5.7 mi (9.2 km) from Lake Chippewa. Callahan Lake and Round ...

4.8/5Exceptional! (31 reviews)
Nice clean

"Great place to atay"…"

Reviewed on Oct 29, 2020

Amazing Sunsets, Peaceful, Well Maintained Lake Home on Beautiful, Barker Lake
Honey Bear Hideaway - Studio Cabin in the Heart of Hayward!

Honey Bear Hideaway - Studio Cabin in the Heart of Hayward!

Hayward, WI
The price is $79 per night from Dec 8 to Dec 9

Situated on a river, this cabin is within a 10-minute walk of Hayward Lake and National Fresh Water Fishing Hall of Fame and Museum. Lumberjack Bowl and Hayward ...

4.5/5Wonderful! (18 reviews)
It truly was so cute and clean relaxing! We just loved it recommended for anyone to get away and wa

"Was so relaxing quiet and so cozy! Thanks for letting us stay there we loved it!!! Thank you again for the cuteness of this place! We got treats in a stocking, candy and s’mores with sticks for fire pit right by a river beautiful!!!"…"

Reviewed on Nov 27, 2020

Honey Bear Hideaway - Studio Cabin in the Heart of Hayward!
Fancy Fireflies - Charming Studio Cabin Amidst the Trees Right on Lake Hayward!

Fancy Fireflies - Charming Studio Cabin Amidst the Trees Right on Lake Hayward!

Hayward, WI
The price is $79 per night from Dec 6 to Dec 7

Situated in Hayward, this cabin is within a 10-minute walk of Hayward Lake and National Fresh Water Fishing Hall of Fame and Museum. Lumberjack Bowl and Hayward ...

4.9/5Exceptional! (12 reviews)
Cute and Cozy

"Perfect get away for a couple !"…"

Reviewed on Oct 14, 2020

Fancy Fireflies - Charming Studio Cabin Amidst the Trees Right on Lake Hayward!
2 Bedroom Lakeside Cabin-family Fishing Resort-hayward Wi-chippewa Flowage

2 Bedroom Lakeside Cabin-family Fishing Resort-hayward Wi-chippewa Flowage

Hayward, WI

This family-friendly Hayward cabin is located on the waterfront, 2.9 mi (4.6 km) from Callahan Lake, and within 6 mi (10 km) of Round Lake and Chequamegon National ...

4.6/5Exceptional! (18 reviews)
Musky Joe’s Vrbo

"Older property/ resort but clean functional and reasonable will come again ."…"

Reviewed on Oct 2, 2020

2 Bedroom Lakeside Cabin-family Fishing Resort-hayward Wi-chippewa Flowage
Yellow Bike Chalet on Grindstone Lake Sleeps up to 14

Yellow Bike Chalet on Grindstone Lake Sleeps up to 14

Hayward, WI

Situated on the waterfront, this romantic cabin is 0.1 mi (0.1 km) from Grindstone Lake and 2 mi (3.2 km) from Lac Courte Oreilles. Hayward Lake and Schoolhouse ...

5/5Exceptional! (15 reviews)
YBC

"We had a great time at the yellow bike chalet. Steve and Janette were gracious hosts. So many beautiful memories from the trip!"…"

Reviewed on Oct 2, 2020

Yellow Bike Chalet on Grindstone Lake Sleeps up to 14
Telemark Vacation Condominiums

Telemark Vacation Condominiums

3.5 out of 5
15315 Nordmor Rd, Cable, WI
The price is $125 per night from Dec 2 to Dec 3

Situated in Cable, this condo building is 4.1 mi (6.6 km) from Cable Natural History Museum and 5.2 mi (8.4 km) from Chequamegon National Forest. American Birkebeiner ...

4.3/5Excellent! (60 reviews)
A little dated but clean

"A little dated but clean. Beautiful location"…"

Reviewed on Oct 21, 2020

Telemark Vacation Condominiums
Secluded Cabin on 13 Acres; Private 50 Acre Lake

Secluded Cabin on 13 Acres; Private 50 Acre Lake

Hayward, WI

Situated on a lake, this romantic cabin is 1.1 mi (1.8 km) from Round Lake and 2 mi (3.2 km) from Tiger Cat Flowage. American Birkebeiner Trail and Hayward Lake ...

4.9/5Exceptional! (70 reviews)
Beautiful cabin by lake

"Cabin was nicer even than expected. Great common space. Open feeling. Wonderful deck and dock to relax Screened in porch fantastic for doing yoga and watching nature. Lake was perfect. We even caught a fish!!!"…"

Reviewed on Oct 18, 2020

Secluded Cabin on 13 Acres; Private 50 Acre Lake
Authentic German Log Cabin in Hayward!!

Authentic German Log Cabin in Hayward!!

Hayward, WI

Located in the heart of Hayward, this cabin is within a 10-minute walk of Hayward Lake and National Fresh Water Fishing Hall of Fame and Museum. Lumberjack Bowl ...

4.8/5Exceptional! (17 reviews)
Great location and stay!

"This was a great location for a family looking for a lot to do! It was right on the water, walking distance from the beach, parks & downtown, the fishing hall of fame, the amusement center, and very close to the wilderness walk zoo. The cabin itself was cozy for a family of 4, but the outdoor aspect ..."…"

Reviewed on Aug 12, 2020

Authentic German Log Cabin in Hayward!!
Sunset On The Bay 3 Bedroom Hotel Room

Sunset On The Bay 3 Bedroom Hotel Room

3 out of 5
12669 Small Road, Unit H7, Hayward, WI

Situated in Hayward, this aparthotel is 0.1 mi (0.1 km) from Nelson Lake and within 9 mi (15 km) of American Birkebeiner Trail and Park Theater. Hayward Information ...

Sunset On The Bay 3 Bedroom Hotel Room
Newly Remodeled-gorgeous View-family Fishing Resort-hayward Wi-chippewa Flowage

Newly Remodeled-gorgeous View-family Fishing Resort-hayward Wi-chippewa Flowage

Hayward, WI
The price is $63 per night from Dec 7 to Dec 8

This Hayward cabin is on the beach, 2.9 mi (4.6 km) from Callahan Lake, and within 6 mi (10 km) of Round Lake and Chequamegon National Forest. Tiger Cat Flowage ...

3.9/5Good! (8 reviews)
Fall Fishing on the Flowage

"I went for a Musky Fishing long weekend. I was able to find the place and its proximity to Hayward was good. The Duplex was in very good shape as it was recently renovated! Very nice to find a good clean place."…"

Reviewed on Sep 23, 2020

Newly Remodeled-gorgeous View-family Fishing Resort-hayward Wi-chippewa Flowage
Rustic and Charming Cabin in Richardson Bay on Round Lake

Rustic and Charming Cabin in Richardson Bay on Round Lake

Hayward, WI

Situated in Hayward, this cabin is 0.1 mi (0.1 km) from Round Lake and within 6 mi (10 km) of Callahan Lake and Tiger Cat Flowage. Grindstone Lake and Hayward ...

5/5Exceptional! (12 reviews)
Excellent Northwood Ambience

"Charming, well-furnished, comfortable cabin, tastefully decorated in Northwoods decor. All of our needs were met perfectly. Will plan to return. Thank you, Jean!"…"

Reviewed on Oct 15, 2020

Rustic and Charming Cabin in Richardson Bay on Round Lake
Get Away From it all at Tranquility on Beautiful Teal Lake "the Quiet Lake"

Get Away From it all at Tranquility on Beautiful Teal Lake "the Quiet Lake"

Hayward, WI

Situated on the waterfront, this romantic cabin is steps from Chequamegon National Forest and Teal Lake. Teal Wing Golf Club is 0.7 mi (1.1 km) away.

5/5Exceptional! (13 reviews)
Peace and tranquillity

"Got very lucky with beautiful weather in November! Cabin was spacious, clean, and with everything I needed. Beautiful view of the lake. Peaceful walks along the golf course. Highly recommend!"…"

Reviewed on Nov 12, 2020

Get Away From it all at Tranquility on Beautiful Teal Lake "the Quiet Lake"
Cabin W/dock on Lake Chetac - 30 Mins to Hayward!

Cabin W/dock on Lake Chetac - 30 Mins to Hayward!

Birchwood, WI

Situated on the waterfront, this cabin is 0.1 mi (0.1 km) from Lake Chetac and 10.5 mi (16.9 km) from Lac Courte Oreilles. Schoolhouse Lake and Grindstone Lake ...

4.8/5Exceptional! (25 reviews)
Fun girls weekend trip

"Location and home itself was great. Beautiful deck overlooking the lake and we were fortunate enough to have perfect weather. Only a couple negatives. The TV in the man seating area did not work. We reported this shortly after our arrival and were told there is no ‘TV’ at the property, only Netflix, ..."…"

Reviewed on Oct 6, 2020

Cabin W/dock on Lake Chetac - 30 Mins to Hayward!
Family Cabin on Burns Lake W/dock & Kayak Rental!

Family Cabin on Burns Lake W/dock & Kayak Rental!

Hayward, WI

Located in Hayward, this family-friendly cabin is 0.3 mi (0.5 km) from Tiger Cat Flowage, and within 9 mi (15 km) of Round Lake and Callahan Lake. Lost Land ...

4.9/5Exceptional! (15 reviews)
Relaxing Get Away

"Well stocked property! Everything we needed for making meals while staying and a great selection for games and entertainment"…"

Reviewed on Nov 2, 2020

Family Cabin on Burns Lake W/dock & Kayak Rental!
Pamper Yourself With Rare Comfort!

Pamper Yourself With Rare Comfort!

Hayward, WI

This family-friendly Hayward chalet is located on the waterfront, within 1 mi (2 km) of Lac Courte Oreilles and Grindstone Lake. Schoolhouse Lake and Round Lake ...

4.9/5Exceptional! (56 reviews)
Great house and swimming beach. Great lake for boating and a couple good restaurants accessible by

"would do this one again"…"

Reviewed on Aug 28, 2020

Pamper Yourself With Rare Comfort!
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See all available properties in Winter
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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.

Vacation Rentals in Winter

Search for Vacation Rentals in Winter on Expedia.com! You can easily find your home rentals, villas, short-term apartments for rent in Winter using one of the methods below: 

  • View our selection of featured home rentals in Winter
  • Use the map to find apartments and other vacation rentals in the Winter neighbourhood you prefer
  • Enter your travel dates to view the best deals on vacation 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 vacation rental in Winter?
Yes, you can find vacation rentals near top attractions in Winter, or you can choose a more secluded option if you’re looking for relaxation.
What's the top vacation rental in Winter?
North Wisconsin Private Island Vacation Home!!: Visitors give good reviews to this Winter vacation home rental, which is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and a hot tub. Our travelers also rate Beautiful 3 bedroom lake home near Winter, Wisconsin. as a favorite home for rent in Winter.
How many vacation rentals are there in Winter?
Choose from 5 Expedia vacation rentals in Winter for a memorable vacation.
What can I see and do in Winter?
Chequamegon National Forest and Lake Chippewa are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find Teal Wing Golf Club and Tiger Cat Flowage.
What are vacation rentals like in Winter?
Vacation rentals are privately owned accommodations you can stay in for several days or longer in Winter. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you’ll have a home away from home. If you’re concerned about cleanliness, vacation rentals can offer a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you a great travel experience. You’ll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for a small group gathering.

Other types of properties in Winter you may be interested in

North Wisconsin Private Island Vacation Home!!

North Wisconsin Private Island Vacation Home!!

Winter, WI
North Wisconsin Private Island Vacation Home!!
Bears Den on Private Lake

Bears Den on Private Lake

Winter, WI
Bears Den on 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.