Town of Winter Rentals
From $343 per night (USD)VRBO
\"Upscale Accommodations\" with an \"Up North\" location!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
No surprise cleaning fees!!! Welcome to "moxi Lodge!" This three bedroom one bath unit will be sure to keep you comfor ...
From $343 per night (USD)VRBO
From $203 per night (USD)Expedia
Pets & kid Friendly ,direct access to ATV& snow trails, private dock
- Bedrooms:
- 0
- Bathrooms:
- 2
- Sleeps:
- 5
Cozy, clean, well-equipped & fully furnished, 4-season cottage on Lake of the Pines in the heart of the Flambeau River S ...
From $203 per night (USD)Expedia
From $185 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 $185 per night (USD)VRBO
From $332 per night (USD)Expedia
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 $332 per night (USD)Expedia
From $195 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 $195 per night (USD)VRBO
From $344 per night (USD)VRBO
Peaceful Cabin on Lake with Pontoon-Fall dates still open.
- 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 $344 per night (USD)VRBO
From $174 per night (USD)VRBO
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 $174 per night (USD)VRBO
From $174 per night (USD)Expedia
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 $174 per night (USD)Expedia
From $389 per night (USD)VRBO
Newer Luxury Getaway in a Tranquil Setting
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Bumblebee Cove! Families and children welcomed! Our newly built cabin is located on beautiful Black Dan Lak ...
From $389 per night (USD)VRBO
From $406 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 $406 per night (USD)VRBO
From $289 per night (USD)VRBO
The Lakeside - Hot Tub, Dog Friendly, Trail Acces - Pontoon Rental - 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 $289 per night (USD)VRBO
From $658 per night (USD)Expedia
Haven Island on Lake Winter - Private Island!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 14
*3 Night Minimum stay for the rest of the 2025 season!* Escape to Haven Island – Your Private Northwoods Paradise ...
From $658 per night (USD)Expedia
From $285 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 $285 per night (USD)VRBO
From $166 per night (USD)Expedia
Rustic Cabin on Private Lake
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
This property showcases Perch Lake in a panoramic view. Whether you are sitting on the deck or on the dock you can obser ...
From $166 per night (USD)Expedia
From $134 per night (USD)VRBO
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 $134 per night (USD)VRBO
From $305 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 $305 per night (USD)VRBO
From $618 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 $618 per night (USD)VRBO
From $383 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 $383 per night (USD)Expedia
From $307 per night (USD)VRBO
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 $307 per night (USD)VRBO
From $115 per night (USD)Expedia
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 $115 per night (USD)Expedia
From $115 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 $115 per night (USD)VRBO
From $233 per night (USD)Expedia
River retreat with excellent fishing & kayaking from dock.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Our Chippewa River retreat will offer a tranquil escape where hunting, fishing, 4 wheeling and swimming are a stones thr ...
From $233 per night (USD)Expedia
From $105 per night (USD)VRBO
EAGLE LODGE - Cozy Cabin Overlooking the Beautiful E. Fork of the Chippewa River
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This beautiful little cabin is 1 of 3 at Eagle Lodge Resort & Campground, has a great view of the river, your only about ...
From $105 per night (USD)VRBO
From $184 per night (USD)Expedia
EAGLE LODGE - Large log cabin on the E. Fork of Chippewa River
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 9
This 2 bedroom cabin (1 or 3 at Eagle Lodge Resort & Campground) is spacious for your whole family and offers 2 living r ...
From $184 per night (USD)Expedia
From $185 per night (USD)VRBO
EAGLE LODGE - River Retreat - amazing views of the East Fork of the Chippewa Rvr
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This is 1 of 3 log cabins situated within Eagle Lodge Resort & Campground. These cabins are within 50ft of the water, so ...
From $185 per night (USD)VRBO
From $294 per night (USD)VRBO
Three Little Birds Cabin
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Three Little Birds Cabin is a spacious retreat located on the Chippewa River near Winter, WI. This pet-friendly cabin ac ...
From $294 per night (USD)VRBO
From $115 per night (USD)VRBO
Charming 2-bedroom house near Loretta
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Get ready to relax in this 2-bedroom house just outside Loretta. This recently remodeled property features 1 king bed, 1 ...
From $115 per night (USD)VRBO