Town of Winter Rentals
From $413 per night (USD)VRBO
Log cabin on beautiful clear lake perfect for your family retreat.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This family friendly log cabin is for those who truly want to avoid the crowds. At the end of a dead-end paved road the ...
From $413 per night (USD)VRBO
From $417 per night (USD)Expedia
Luxury Getaway in a Tranquil Setting
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Bumblebee Cove! Families and children welcomed! Our custom built cabin is located on beautiful Black Dan La ...
From $417 per night (USD)Expedia
From $257 per night (USD)VRBO
Amazing Sunsets, Peaceful, Well Maintained Lake home on Beautiful, Barker lake
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 12
This is a two bedroom, four season lake home. It has a large extra room that we use as an extra living room and bunk h ...
From $257 per night (USD)VRBO
From $506 per night (USD)Expedia
Bears Den on the private lake
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
The Bears Den is a private cabin, located on a private lake that does not have public boat access. There are neighbors o ...
From $506 per night (USD)Expedia
From $320 per night (USD)VRBO
Peaceful Cabin on Lake
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This is a "true" up north cabin, surrounded by nature, water and recreation. Cabin is located on 273 acre Lake of the Pi ...
From $320 per night (USD)VRBO
From $203 per night (USD)Expedia
Cozy cabin on Island Lake
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Fantastic 3 Season Rental on Island Lake just northeast of Winter, WI and approximately 30 minutes east of Hayward, WI. ...
From $203 per night (USD)Expedia
From $203 per night (USD)VRBO
Cozy cabin on Island Lake
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Great 3 Season Cabin available for rent on Island Lake just northeast of Winter, WI and approximately 30 minutes east of ...
From $203 per night (USD)VRBO
From $239 per night (USD)VRBO
Cabin in the Woods Near Big Chip and Hayward
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Secluded cabin near the Chippewa Flowage and Hayward. Modern 2 bedroom plus loft on 80 acres with direct access to ATV t ...
From $239 per night (USD)VRBO
From $378 per night (USD)VRBO
5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 10
Located on the East side of Barber lake. This 1 acre 4 bedroom 3 bath lake home holds up to 8 people per Sawyer County r ...
From $378 per night (USD)VRBO
From $235 per night (USD)VRBO
Great 4 Season Family Getaway! Quiet, yet full of Fun!
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 10
This one's got it all at an affordable price! Awesome views of the clear water lake from the porch and full front deck! ...
From $235 per night (USD)VRBO
From $148 per night (USD)VRBO
Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Two Bedroom Cabin with a beautiful view of Barker Lake and the Eastern Fork of the Chippewa Flowage. Trails for Snowmobi ...
From $148 per night (USD)VRBO
From $481 per night (USD)Expedia
Park and Ride-Lucky Charlie is on ATV/Snowmobile trail and fish Lake Winter.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Lucky Charlie Lodge is a 3-bedroom 2-bath vacation home on Lake Winter. This Vacation Home has it all; an open layout wi ...
From $481 per night (USD)Expedia
From $252 per night (USD)VRBO
Rustic Cabin on Private Lake
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This property showcases Perch Lake in a panoramic view. Whether you are sitting on the deck or on the dock you can obser ...
From $252 per night (USD)VRBO
From $164 per night (USD)Expedia
Bucktail Lodge Pineview cabin on Winter, Wisconsin.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 10
Pineview Cabin is our largest cabin at Bucktail Lodge out of four cabins, with the ability to sleep up to 10. Beautiful ...
From $164 per night (USD)Expedia
From $157 per night (USD)VRBO
Winter Nights Cottages: Cottage 3 Winter, Wisconsin vacation rental.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to our cozy one-bedroom humble abode! This cottage is nestled away in the quiet town of WInter, WI. During your ...
From $157 per night (USD)VRBO
From $146 per night (USD)Expedia
Winter Nights Cottages: Cottage 1 Winter, Wisconsin vacation rental.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 7
Welcome to our cozy one-bedroom humble abode! This cottage is nestled away in the quiet town of WInter, WI. During your ...
From $146 per night (USD)Expedia
From $156 per night (USD)VRBO
Winter Nights Cottages: Cottage 5 Winter, Wisconsin vacation rental.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Welcome to your home away from home! Our one-bedroom, one-bathroom cozy cottage will make you and your guests never want ...
From $156 per night (USD)VRBO
From $163 per night (USD)Expedia
Winter Nights Cottages: Cottage 4 Winter, Wisconsin vacation rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 7
ou’ve never “glamped” like this before! Our one-bedroom, one-bathroom cozy, secluded, little cottage will have you feeli ...
From $163 per night (USD)Expedia
From $424 per night (USD)VRBO
Welcome to The Hideaway on Highland.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our cozy 3 bedroom, 1 bathroom cabin(newly constructed), the perfect place for year-round fun! Nestled just 0 ...
From $424 per night (USD)VRBO
From $738 per night (USD)VRBO
Hunter Lake Lodge awaits...
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 13
Our gorgeous lodge nestled in the pines boasts an open floorplan with a beautiful 2-story wall of windows looking out on ...
From $738 per night (USD)VRBO
From $2084 per night (USD)VRBO
Historic prohibition Lodge next to golf course with private beach
- Bedrooms:
- 5
- Bathrooms:
- 10
- Sleeps:
- 45
Legacy Lodge is an eloquent historic lodge with an additional five cabins on the property! Offering accommodations for u ...
From $2084 per night (USD)VRBO
From $249 per night (USD)Expedia
Bobbers Cabin on Perch Lake
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
About this space: This cozy cabin is tucked away in the woods and offers an easy approach and spectacular lake views of ...
From $249 per night (USD)Expedia
From $148 per night (USD)VRBO
Bucktail Lodge Lakeview Cabin on Barker Lake in Winter, Wisconsin
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Just off a 260+ acre lake and part of the East Fork of the Chippewa Flowage. This two bedtime cabin has plenty of lake a ...
From $148 per night (USD)VRBO
From $318 per night (USD)VRBO
Pfaff Winter Retreat on Lake Winter. Minutes from Tuscobia trail.
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Our peaceful retreat offers beautiful sunrises on Lake Winter. Our home has 5 bedrooms and 2.5 bathrooms. Enjoy fishing ...
From $318 per night (USD)VRBO
From $613 per night (USD)VRBO
The Lakeside - Hot Tub, Dog Friendly, Trail Acces - On Lake Winter
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Discover `The Lakeside` on Lake Winter! Perfect for 8 guests across 4 bedrooms, this retreat is your ideal escape. Unwin ...
From $613 per night (USD)VRBO
From $416 per night (USD)Expedia
Luxury Cabin, 800+ feet frontage, 733 acre Lake, Hot tub, Pontoon, Fireplace .
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Öur Cabin was originally built in 1979 using the butt-and pass method with full logs. In 2022 the Magnuson family fully ...
From $416 per night (USD)Expedia
From $211 per night (USD)VRBO
Private, Pet Friendly Lakefront Cabin
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This year-round 2 bedroom, 1 bath cabin is the perfect getaway for a family vacation, a couple's long weekend or a frien ...
From $211 per night (USD)VRBO
From $238 per night (USD)Expedia
Right on the Tuscobia Trail Cozy 2-bedroom cabin in Winter with WiFi, AC
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This memorable cabin is the perfect home base for your trip to Winter. Lake Winter public access is 5 min away, and it s ...
From $238 per night (USD)Expedia
From $806 per night (USD)VRBO
Private Island on Lake Winter
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 14
*Flexible three night stays for the rest of the 2026 season! 2027 Summer calendar open, Saturday check in and Saturday c ...
From $806 per night (USD)VRBO
From $699 per night (USD)Expedia
The Lodge on Lake of the Pines - enjoy the Northwoods in comfort!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
The Lodge was newly constructed in 2024 and offers 4 bedrooms, including all 4 rooms with a queen bed and 2 rooms with 2 ...
From $699 per night (USD)Expedia
From $231 per night (USD)VRBO
Classic Rustic Lakeside Cabin Retreat. Sleeps 6. Pets allowed.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Bluegill Cabin is the quintessential northern Wisconsin cabin; cozy, private, with lots of rustic charm. Situated on ne ...
From $231 per night (USD)VRBO
From $271 per night (USD)Expedia
Cozy 3 bedroom home in heart of Winter WI…Pet Budget and Family Friendly!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy a peaceful stay at this 3-bedroom house in Winter. The space features one king bed and three queen beds, perfect f ...
From $271 per night (USD)Expedia
From $303 per night (USD)VRBO
Cozy 2-bedroom cabin on beautiful Connor’s Lake w/ AC and WiFi, UTV trails near
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Unwind on Connor’s Lake at this charming cabin. With two cozy bedrooms featuring queen beds, plus a living room with a f ...
From $303 per night (USD)VRBO
From $366 per night (USD)Expedia
Sunset Point on Winter Lake
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 10
Escape to Winter Lake! This private 3-acre retreat features 175' of frontage on a premier Class A musky and walleye lake ...
From $366 per night (USD)Expedia