Town of Winter Rentals
- 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 $171 per night (USD)
Expedia
Pets & kid Friendly ,direct access to ATV\/snow trail, clear lake, sandy bottom
- Bedrooms:
- 1
- 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 $171 per night (USD)Expedia
- From $110 per night (USD)
VRBO
Bungalow Trail
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Come stay in this 2 bedroom modern bungalow that puts you next to all the amenities that the Northwoods has to offer. Ac ...
From $110 per night (USD)VRBO
- From $200 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 $200 per night (USD)Expedia
- From $325 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 $325 per night (USD)VRBO
- From $200 per night (USD)
Expedia
\"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 $200 per night (USD)Expedia
- From $225 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 comfort ...
From $225 per night (USD)VRBO
- From $810 per night (USD)
VRBO
Exclusive PRIVATE ISLAND for your group on Lake Winter
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 14
This island is unique in that you don't share it will any other parties, just yours! Escape to Haven private Island! A s ...
From $810 per night (USD)VRBO
- From $488 per night (USD)
VRBO
6 bedroom 3- bath 16 people capacity pontoon included in Winter Wis.
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 16
Located on the East side of Barber lake. This 1 acre 6 bedroom 3 bath lake home holds up to 16 people max. Pontoon inclu ...
From $488 per night (USD)VRBO
- 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 $203 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 $203 per night (USD)VRBO
- From $149 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 $149 per night (USD)Expedia
- From $245 per night (USD)
VRBO
The Lakeside - Hot Tub, Dog Friendly, on Trails - 4BR - On Lake Winter *NEW*
- Bedrooms:
- 2
- 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 $245 per night (USD)VRBO
- From $250 per night (USD)
VRBO
A Family Vacation is still Affordable
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
This four bedroom cabin is located just 30' from the water's edge on this quiet sportsmen's lake. The call of the loon ...
From $250 per night (USD)VRBO
- From $147 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 $147 per night (USD)VRBO
- From $160 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 $160 per night (USD)Expedia
- From $150 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 $150 per night (USD)VRBO
- From $288 per night (USD)
VRBO
Peaceful Cabin on Lake with Pontoon-Memorial Wknd Still Available 2024
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
This is a "true" up north cabin, surrounded by nature, water and recreation. Cabin is located on 273 acre Lake of the Pi ...
From $288 per night (USD)VRBO
- From $385 per night (USD)
VRBO
Bring the Family to our Wonderful Log Cabin on Connors Lake!
- 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 $385 per night (USD)VRBO
- From $400 per night (USD)
VRBO
A little piece of heaven in northern wisconsin
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Our cabin is located on Conners Lake in the Flambeau Forest. Surrounded by beauty, lots of wildlife and located on 100's ...
From $400 per night (USD)VRBO
- From $349 per night (USD)
VRBO
Newer Luxury Getaway in a Tranquil Setting
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to Bumblebee Cove! Families and children welcomed! Our newly built cabin is located on beautiful Black Dan Lak ...
From $349 per night (USD)VRBO
- From $441 per night (USD)
VRBO
Private Modern Home in Rustic Surroundings
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
This home has the privacy you like and yet activities for all seasons. There is fishing on Barker Lake to catch Muskie, ...
From $441 per night (USD)VRBO
- From $145 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 $145 per night (USD)VRBO
- From $126 per night (USD)
Expedia
Bucktail Lodge Pineview cabin on Winter, Wisconsin.
- Bedrooms:
- 2
- 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 $126 per night (USD)Expedia
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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 ...
Click For PricingVRBO
- From $408 per night (USD)
Expedia
Winter retreat on Lake Winter. Minutes from Tuscobia trail.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Our peaceful retreat offers beautiful sunrises on Lake Winter. Our home has 5 bedrooms and 2.5 bathrooms, open yet space ...
From $408 per night (USD)Expedia
- From $240 per night (USD)
VRBO
Renewed Lakeside Retreat with Stunning View
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to our cozy cedar filled cabin nestled among tall pines overlooking Barber Lake near Winter, WI. Featuring modern ...
From $240 per night (USD)VRBO
- From $207 per night (USD)
Expedia
Beautiful sunsets, cozy renovated home, kayaks, peddle boat, Wi-Fi, small dogs
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Newly renovated 4 season cottage: lake fun, close to ATV trails, wi-fi, and pet friendly. Two bedroom, 1 bath, 1000 sq ...
From $207 per night (USD)Expedia
- From $225 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 $225 per night (USD)VRBO
- From $335 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 $335 per night (USD)Expedia
- From $550 per night (USD)
VRBO
It's summertime on Hunter Lake! Step out of winter...in Winter, WI!
- 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 $550 per night (USD)VRBO
- From $135 per night (USD)
Expedia
ATV\/Snowmobiling Cozy Retreat
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Newly Renovated WI cabin! This is a private setting with your own private driveway and yard, down the street there is a ...
From $135 per night (USD)Expedia
- From $100 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 $100 per night (USD)VRBO
- From $106 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 $106 per night (USD)Expedia
- From $106 per night (USD)
VRBO
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, ...
From $106 per night (USD)VRBO
- Click For Pricing
Expedia
Northwoods
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful cabin on 400+ acre Connors Lake in the Town of Winter. Located in the heart of the Flambeau River State Forest ...
Click For PricingExpedia
- Click For Pricing
Expedia
The Happy Porcupine Cottage - ATV, Hiking, Fishing, Relaxation and Supper Clubs!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Come explore the Wisconsin Northwoods! The Happy Porcupine Cottage is located near an abundant amount of lakes, rivers a ...
Click For PricingExpedia
- Click For Pricing
Expedia
Motel in Sawyer County in Wisconsin on ATV and snowmobile trails.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Fischers’ Trap and Fish Motel is located near Trail #5. Located under 20 minutes from the beautiful Chippewa Flowage. Y ...
Click For PricingExpedia
- Click For Pricing
Expedia
Motel in Sawyer County in Wisconsin on ATV\/Snowmobile trails.
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 0
Fischers’ Trap and Fish Motel has a studio room available with queen bed, Kitchenette and medium size refrigerator. W ...
Click For PricingExpedia
- From $165 per night (USD)
Expedia
The Happy Porcupine Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to The Happy Porcupine Cottage, your charming retreat nestled in the heart of Sawyer County, serving as the perf ...
From $165 per night (USD)Expedia
- From $250 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 $250 per night (USD)VRBO
- From $200 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 $200 per night (USD)Expedia
- From $106 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 $106 per night (USD)VRBO
- From $100 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 $100 per night (USD)Expedia
- From $100 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 $100 per night (USD)VRBO
- From $100 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 $100 per night (USD)Expedia
- Click For Pricing
VRBO
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 ...
Click For PricingVRBO
- From $125 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 $125 per night (USD)Expedia
- From $225 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 $225 per night (USD)VRBO
- From $200 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 $200 per night (USD)Expedia
- From $211 per night (USD)
VRBO
Sleeps 12, Allows Dogs! Minutes from Chippewa Flowage Boat Landing!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
This great cabin is located at the head of the Chippewa river below the dam of the Chippewa flowage. The boat ramp is lo ...
From $211 per night (USD)VRBO