Monthly & Short Term Vacation Rentals in Winter, WI

Compare 380 available, short term lakefront holiday vacation home properties, starts from $55

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ACCOMMODATION TYPES

Cheap Monthly & Short Term Vacation Rentals in Winter, WI: Top Deals

Lucky Charlie Lodge 3 Bedroom Home by Redawning
Lucky Charlie Lodge 3 Bedroom Home by Redawning
Lucky Charlie Lodge 3 Bedroom Home by Redawning
Lucky Charlie Lodge 3 Bedroom Home by Redawning
Lucky Charlie Lodge 3 Bedroom Home by Redawning
Holiday home · 2 Guests · 1 Bedroom
$375 /night
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The Yellow House on the Lake. Private Waterfront Cabin in Hayward, WI.
The Yellow House on the Lake. Private Waterfront Cabin in Hayward, WI.
The Yellow House on the Lake. Private Waterfront Cabin in Hayward, WI.
The Yellow House on the Lake. Private Waterfront Cabin in Hayward, WI.
10 (4 reviews)
The Yellow House on the Lake. Private Waterfront Cabin in Hayward, WI.
Cabin · 2 Guests · 1 Bedroom
$195 /night*
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4 Season-3bed-2bath on Round Lake, close to Birkie and right on snowmobile trail
4 Season-3bed-2bath on Round Lake, close to Birkie and right on snowmobile trail
4 Season-3bed-2bath on Round Lake, close to Birkie and right on snowmobile trail
4 Season-3bed-2bath on Round Lake, close to Birkie and right on snowmobile trail
9.8 (27 reviews)
4 Season-3bed-2bath on Round Lake, close to Birkie and right on snowmobile trail
Holiday home · 2 Guests · 1 Bedroom
$170 /night*
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#1Lakeside Cabin W/Beautiful Views Of Moose Lake ~ Private Dock with Boat launch
#1Lakeside Cabin W/Beautiful Views Of Moose Lake ~ Private Dock with Boat launch
#1Lakeside Cabin W/Beautiful Views Of Moose Lake ~ Private Dock with Boat launch
#1Lakeside Cabin W/Beautiful Views Of Moose Lake ~ Private Dock with Boat launch
#1Lakeside Cabin W/Beautiful Views Of Moose Lake ~ Private Dock with Boat launch
Cabin · 2 Guests · 1 Bedroom
$250 /night*
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"Upscale Accommodations" with an "Up North" location!
"Upscale Accommodations" with an "Up North" location!
"Upscale Accommodations" with an "Up North" location!
"Upscale Accommodations" with an "Up North" location!
10 (14 reviews)
"Upscale Accommodations" with an "Up North" location!
Resort · 2 Guests · 1 Bedroom
$200 /night*
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New Listing Northwoods Rustic Lodge steps away from Round Lake in Richardson Bay
New Listing Northwoods Rustic Lodge steps away from Round Lake in Richardson Bay
New Listing Northwoods Rustic Lodge steps away from Round Lake in Richardson Bay
New Listing Northwoods Rustic Lodge steps away from Round Lake in Richardson Bay
9.6 (17 reviews)
New Listing Northwoods Rustic Lodge steps away from Round Lake in Richardson Bay
Lodge · 2 Guests · 1 Bedroom
$595 /night*
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English Cottage on Scenic Spring Lake
English Cottage on Scenic Spring Lake
English Cottage on Scenic Spring Lake
English Cottage on Scenic Spring Lake
10 (14 reviews)
English Cottage on Scenic Spring Lake
Holiday home · 2 Guests · 1 Bedroom
$205 /night*
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Private Cabin with Sand Beach on the Chippewa Flowage - Great Fishing!
Private Cabin with Sand Beach on the Chippewa Flowage - Great Fishing!
Private Cabin with Sand Beach on the Chippewa Flowage - Great Fishing!
Private Cabin with Sand Beach on the Chippewa Flowage - Great Fishing!
9.4 (17 reviews)
Private Cabin with Sand Beach on the Chippewa Flowage - Great Fishing!
Cabin · 2 Guests · 1 Bedroom
$450 /night*
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Lac Courte Oreilles*** Newly remodeled Waterfront Cottage Feet From The Lake
Lac Courte Oreilles*** Newly remodeled Waterfront Cottage Feet From The Lake
Lac Courte Oreilles*** Newly remodeled Waterfront Cottage Feet From The Lake
Lac Courte Oreilles*** Newly remodeled Waterfront Cottage Feet From The Lake
10 (59 reviews)
Lac Courte Oreilles*** Newly remodeled Waterfront Cottage Feet From The Lake
Cottage · 2 Guests · 1 Bedroom
$299 /night*
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Pristine View, Great Attention to Detail, All the extras. Just read our reviews!
Pristine View, Great Attention to Detail, All the extras. Just read our reviews!
Pristine View, Great Attention to Detail, All the extras. Just read our reviews!
Pristine View, Great Attention to Detail, All the extras. Just read our reviews!
10 (22 reviews)
Pristine View, Great Attention to Detail, All the extras. Just read our reviews!
Holiday home · 2 Guests · 1 Bedroom
$500 /night*
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Custom Built Luxury Home On Big Round Lake With Game Room and Open Floor Plan
Custom Built Luxury Home On Big Round Lake With Game Room and Open Floor Plan
Custom Built Luxury Home On Big Round Lake With Game Room and Open Floor Plan
Custom Built Luxury Home On Big Round Lake With Game Room and Open Floor Plan
9.8 (40 reviews)
Custom Built Luxury Home On Big Round Lake With Game Room and Open Floor Plan
Cabin · 2 Guests · 1 Bedroom
$375 /night*
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On the Edge of the Water-The Edgewater!
On the Edge of the Water-The Edgewater!
On the Edge of the Water-The Edgewater!
On the Edge of the Water-The Edgewater!
10 (7 reviews)
On the Edge of the Water-The Edgewater!
Cabin · 2 Guests · 1 Bedroom
$150 /night*
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Round Lake Hideaway
Round Lake Hideaway
Round Lake Hideaway
Round Lake Hideaway
9.2 (20 reviews)
Round Lake Hideaway
Cabin · 2 Guests · 1 Bedroom
$400 /night*
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Eaglesnest-Log home, on Lake Chippewa-Friday to Friday for Summer rentals
Eaglesnest-Log home, on Lake Chippewa-Friday to Friday for Summer rentals
Eaglesnest-Log home, on Lake Chippewa-Friday to Friday for Summer rentals
Eaglesnest-Log home, on Lake Chippewa-Friday to Friday for Summer rentals
10 (55 reviews)
Eaglesnest-Log home, on Lake Chippewa-Friday to Friday for Summer rentals
Holiday home · 2 Guests · 1 Bedroom
$399 /night*
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Northwood's Fish Haven on Beautiful Moose Lake WI ~ Stay for the Holidays
Northwood's Fish Haven on Beautiful Moose Lake WI ~ Stay for the Holidays
Northwood's Fish Haven on Beautiful Moose Lake WI ~ Stay for the Holidays
Northwood's Fish Haven on Beautiful Moose Lake WI ~ Stay for the Holidays
9.6 (81 reviews)
Northwood's Fish Haven on Beautiful Moose Lake WI ~ Stay for the Holidays
Holiday home · 2 Guests · 1 Bedroom
$333 /night*
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Lumberjack Lodge: 5 BR, 4.25 BA House in Hayward, Sleeps 14
Lumberjack Lodge: 5 BR, 4.25 BA House in Hayward, Sleeps 14
Lumberjack Lodge: 5 BR, 4.25 BA House in Hayward, Sleeps 14
Lumberjack Lodge: 5 BR, 4.25 BA House in Hayward, Sleeps 14
9.6 (17 reviews)
Lumberjack Lodge: 5 BR, 4.25 BA House in Hayward, Sleeps 14
Holiday home · 2 Guests · 1 Bedroom
$500 /night*
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YEAR-ROUND RENTAL CABIN $119.00 for 2/ Sleeps 6/ $20. extra person per stay
YEAR-ROUND RENTAL CABIN $119.00 for 2/ Sleeps 6/ $20. extra person per stay
YEAR-ROUND RENTAL CABIN $119.00 for 2/ Sleeps 6/ $20. extra person per stay
YEAR-ROUND RENTAL CABIN $119.00 for 2/ Sleeps 6/ $20. extra person per stay
9.8 (57 reviews)
YEAR-ROUND RENTAL CABIN $119.00 for 2/ Sleeps 6/ $20. extra person per stay
Cabin · 2 Guests · 1 Bedroom
$129 /night*
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Custom built Home on Round Lake
Custom built Home on Round Lake
Custom built Home on Round Lake
Custom built Home on Round Lake
9.6 (24 reviews)
Custom built Home on Round Lake
Holiday home · 2 Guests · 1 Bedroom
$600 /night*
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Family Lake Retreat on Lac Courte Oreilles
Family Lake Retreat on Lac Courte Oreilles
Family Lake Retreat on Lac Courte Oreilles
Family Lake Retreat on Lac Courte Oreilles
9.4 (19 reviews)
Family Lake Retreat on Lac Courte Oreilles
Holiday home · 2 Guests · 1 Bedroom
$250 /night*
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Lake Front Cabin steps off Big Sissabagama Lake with NEW Fitness Center & Sauna!
Lake Front Cabin steps off Big Sissabagama Lake with NEW Fitness Center & Sauna!
Lake Front Cabin steps off Big Sissabagama Lake with NEW Fitness Center & Sauna!
Lake Front Cabin steps off Big Sissabagama Lake with NEW Fitness Center & Sauna!
10 (20 reviews)
Lake Front Cabin steps off Big Sissabagama Lake with NEW Fitness Center & Sauna!
Cabin · 2 Guests · 1 Bedroom
$225 /night*
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Similar Inspirational Vacation Rental Destinations

Which Price Range Is Considered As A Good Deal in Winter, WI Area?
Vacation Cabin & House Rental Price Information in Winter, WI
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The graph shows the percentages of vacation homes in each price bucket. Winter has the largest percentage (28.04%) of homes in $100 - $150 price range.
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$500 +
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How Many Accommodations Are Pets Allowed in Winter, WI?
Percentage of Pet Friendly Rental Properties in Winter, WI
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35.79% of vacation homes in Winter are pet friendly. Either you bring your loved pets on vacation or you have pet allergies, make sure to select the homes by applying the right filters.
Is Winter, WI a convenient place to stay?
The Convenience of Winter, WI
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Winter, WI is a great place for monthly rentals. It has a low crime rate compared to other cities in the US and is close to many public transportation options, amenities, business centers, and healthcare facilities. Additionally, there are plenty of grocery stores, pharmacies, restaurants, and other essential amenities within walking distance.

  • Eau Claire Amtrak Station: 45 miles
  • Harmony Co-op Grocery Store: 0.3 miles
  • Hammond Business Center: 2.9 miles
  • St. Joseph's Hospital: 6.4 miles
What Are The Must-Visit Places in Winter, WI?
Destinations To Visit During the Month in Winter, WI
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When you have only limited times to spend in Winter, WI, we highly recommend you to visit those famous places:

Other Vacation Rentals Ideas

* The displayed nightly rate may be estimated based on a future travel date. Narrow down your search with checkin and checkout dates to see the exact price.
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