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Town of Winter Rentals

$\Upscale Accommodations\ with an \Up North\ location!$
From $250 per night (USD)
VRBO
\"Upscale Accommodations\" with an \"Up North\" location!
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
No surprise cleaning fees!!! Welcome to "moxi Lodge!" This three bedroom one bath unit will be sure to keep you comfor ...
From $250 per night (USD)
VRBO
From $217 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 $217 per night (USD)
Expedia
$\Upscale Accommodations\ with an \Up North\ location!$
From $211 per night (USD)
VRBO
\"Upscale Accommodations\" with an \"Up North\" location!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
No surprise cleaning fees!!! Welcome to "moxi Lodge!" This two bedroom one bath upper level unit will be sure to keep y ...
From $211 per night (USD)
VRBO
From $185 per night (USD)
Expedia
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)
Expedia
From $334 per night (USD)
VRBO
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 $334 per night (USD)
VRBO
$\Upscale Accommodations\ with an \Up North\ location!$
From $225 per night (USD)
Expedia
\"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 comfort ...
From $225 per night (USD)
Expedia
From $351 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 $351 per night (USD)
VRBO
From $206 per night (USD)
Expedia
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 $206 per night (USD)
Expedia
From $192 per night (USD)
VRBO
Blue Bungalow on Lake Winter 4 seasons of family fun: Fish/ ATV/Snowmobile/Relax
Bedrooms:
1
Bathrooms:
3
Sleeps:
10
Experience Northern Wisconsin at its finest in this family-friendly bungalow nestled on the shores of Lake Winter. The B ...
From $192 per night (USD)
VRBO
From $157 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 $157 per night (USD)
Expedia
From $152 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 $152 per night (USD)
VRBO
From $300 per night (USD)
Expedia
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 $300 per night (USD)
Expedia
From $179 per night (USD)
VRBO
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 $179 per night (USD)
VRBO
From $348 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 $348 per night (USD)
VRBO
From $170 per night (USD)
VRBO
Summer in Winter (Unit 6)
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 $170 per night (USD)
VRBO
From $170 per night (USD)
Expedia
Summer in Winter (Unit 5)
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 $170 per night (USD)
Expedia
From $162 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 $162 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 $338 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 $338 per night (USD)
VRBO
From $536 per night (USD)
VRBO
Private Modern Home in Rustic Surroundings
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This home has the privacy you like and yet activities for all seasons. When you are done fishing on Barker Lake, you ca ...
From $536 per night (USD)
VRBO
From $170 per night (USD)
VRBO
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 $170 per night (USD)
VRBO
From $137 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 $137 per night (USD)
Expedia
From $1899 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 $1899 per night (USD)
VRBO
From $282 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 $282 per night (USD)
VRBO
From $789 per night (USD)
VRBO
Private Island on Lake Winter
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 An e ...
From $789 per night (USD)
VRBO
From $784 per night (USD)
Expedia
The Lodge on Lake of the Pines - enjoy the Northwoods in comfort!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
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 $784 per night (USD)
Expedia
From $370 per night (USD)
VRBO
Renewed Lakeside Retreat with Stunning View
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
Escape to our cozy cedar filled cabin nestled among tall pines overlooking Barber Lake near Winter, WI (not far from Hay ...
From $370 per night (USD)
VRBO
From $274 per night (USD)
VRBO
Welcome to The Hideaway on Highland.
Bedrooms:
1
Bathrooms:
4
Sleeps:
6
Welcome to our cozy 3 bedroom, 1 bathroom cabin(newly constructed), the perfect place for year-round fun! Nestled just 0 ...
From $274 per night (USD)
VRBO
From $400 per night (USD)
VRBO
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 $400 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 $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 $171 per night (USD)
Expedia
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 $171 per night (USD)
Expedia
From $115 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 $115 per night (USD)
VRBO
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Expedia
Bucktail Lodge Bayview Cabin, view of the East Fork of the Chippewa flowage
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This property is located just outside of Winter, Wisconsin on Barker Lake. No matter what you are looking for, Hunting, ...
Click For Pricing
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 $198 per night (USD)
VRBO
Northwoods Escape in Winter
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
The ultimate getaway for ATV/UTV enthusiasts and nature lovers! Located between Winter and Ojibwa, WI is family cabin is ...
From $198 per night (USD)
VRBO
From $123 per night (USD)
Expedia
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 $123 per night (USD)
Expedia
From $207 per night (USD)
VRBO
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 $207 per night (USD)
VRBO
From $180 per night (USD)
Expedia
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 $180 per night (USD)
Expedia
From $291 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 $291 per night (USD)
VRBO
From $120 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 $120 per night (USD)
VRBO

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Town of Winter Rentals

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Results: 42 Rentals