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Winter Vacation Rentals

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50 rentals in Winter.
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Beautiful 3 bedroom lake home near Winter, Wisconsin., vacation rental in Winter
Beautiful 3 bedroom lake home near Winter, Wisconsin., vacation rental in Winter
Beautiful 3 bedroom lake home near Winter, Wisconsin., vacation rental in Winter

Beautiful 3 bedroom lake home near Winter, Wisconsin.

Rental Home
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Bring the Family to our Wonderful Log Cabin on Connors Lake!, vacation rental in Winter
Bring the Family to our Wonderful Log Cabin on Connors Lake!, vacation rental in Winter
Bring the Family to our Wonderful Log Cabin on Connors Lake!, vacation rental in Winter

Bring the Family to our Wonderful Log Cabin on Connors Lake!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Newly Built - Second Season Renting!  Luxury Getaway in a Tranquil Setting, vacation rental in Winter
Newly Built - Second Season Renting!  Luxury Getaway in a Tranquil Setting, vacation rental in Winter
Newly Built - Second Season Renting!  Luxury Getaway in a Tranquil Setting, vacation rental in Winter

Newly Built - Second Season Renting! Luxury Getaway in a Tranquil Setting

Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Great 4 Season Family Getaway!  Quiet, yet full of Fun!, vacation rental in Winter
Great 4 Season Family Getaway!  Quiet, yet full of Fun!, vacation rental in Winter
Great 4 Season Family Getaway!  Quiet, yet full of Fun!, vacation rental in Winter

Great 4 Season Family Getaway! Quiet, yet full of Fun!

Rental Home
4 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
More info
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Private Modern Home in Rustic Surroundings and Much to Do, vacation rental in Winter
Private Modern Home in Rustic Surroundings and Much to Do, vacation rental in Winter
Private Modern Home in Rustic Surroundings and Much to Do, vacation rental in Winter

Private Modern Home in Rustic Surroundings and Much to Do

Rental Home
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
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Up North Cabin with Pontoon. Winter Ice Fishing and Snowmobiling Trails., vacation rental in Winter
Up North Cabin with Pontoon. Winter Ice Fishing and Snowmobiling Trails., vacation rental in Winter
Up North Cabin with Pontoon. Winter Ice Fishing and Snowmobiling Trails., vacation rental in Winter

Up North Cabin with Pontoon. Winter Ice Fishing and Snowmobiling Trails.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Bears Den on Private Lake, vacation rental in Winter
Bears Den on Private Lake, vacation rental in Winter
Bears Den on Private Lake, vacation rental in Winter

Bears Den on Private Lake

Rental Home
5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
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Eaglesnest-Log home, on Lake Chippewa-Pontoon boat for rent-44 five star reviews, vacation rental in Winter
Eaglesnest-Log home, on Lake Chippewa-Pontoon boat for rent-44 five star reviews, vacation rental in Winter
Eaglesnest-Log home, on Lake Chippewa-Pontoon boat for rent-44 five star reviews, vacation rental in Winter

Eaglesnest-Log home, on Lake Chippewa-Pontoon boat for rent-44 five star reviews

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Super Private...Amazing Views...Quiet Solitude!!, vacation rental in Winter
Super Private...Amazing Views...Quiet Solitude!!, vacation rental in Winter
Super Private...Amazing Views...Quiet Solitude!!, vacation rental in Winter

Super Private...Amazing Views...Quiet Solitude!!

Rental Home
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Ice Fish & Snowmobile on the Famous Chippewa Flowage in Hayward, WI, vacation rental in Winter
Ice Fish & Snowmobile on the Famous Chippewa Flowage in Hayward, WI, vacation rental in Winter
Ice Fish & Snowmobile on the Famous Chippewa Flowage in Hayward, WI, vacation rental in Winter

Ice Fish & Snowmobile on the Famous Chippewa Flowage in Hayward, WI

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Amazing Lake Home With Room For The Whole Family, vacation rental in Winter
Amazing Lake Home With Room For The Whole Family, vacation rental in Winter
Amazing Lake Home With Room For The Whole Family, vacation rental in Winter

Amazing Lake Home With Room For The Whole Family

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Lakefront Hayward Home w/ Fire Pit by Ski Trails!, vacation rental in Winter
Lakefront Hayward Home w/ Fire Pit by Ski Trails!, vacation rental in Winter
Lakefront Hayward Home w/ Fire Pit by Ski Trails!, vacation rental in Winter

Lakefront Hayward Home w/ Fire Pit by Ski Trails!

Rental Home
3 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
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Lakefront Cabin on the Chippewa Flowage Near Hayward, Wisconsin, vacation rental in Winter
Lakefront Cabin on the Chippewa Flowage Near Hayward, Wisconsin, vacation rental in Winter
Lakefront Cabin on the Chippewa Flowage Near Hayward, Wisconsin, vacation rental in Winter

Lakefront Cabin on the Chippewa Flowage Near Hayward, Wisconsin

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Amazing Sunsets, Peaceful, Well Maintained  Lake home on Beautiful, Barker lake, vacation rental in Winter
Amazing Sunsets, Peaceful, Well Maintained  Lake home on Beautiful, Barker lake, vacation rental in Winter
Amazing Sunsets, Peaceful, Well Maintained  Lake home on Beautiful, Barker lake, vacation rental in Winter

Amazing Sunsets, Peaceful, Well Maintained Lake home on Beautiful, Barker lake

Rental Home
2 bedrooms
1 bathroom
Sleeps 12
Match: Sleeps
More info
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Outdoor Enthusiasts Paradise!  Fishing, Snowmobiling And Four-Wheeling ..., vacation rental in Winter
Outdoor Enthusiasts Paradise!  Fishing, Snowmobiling And Four-Wheeling ..., vacation rental in Winter
Outdoor Enthusiasts Paradise!  Fishing, Snowmobiling And Four-Wheeling ..., vacation rental in Winter

Outdoor Enthusiasts Paradise! Fishing, Snowmobiling And Four-Wheeling ...

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Captivating Views of Lake Chippewa from Three Level Chalet Cabin & Lake Home, vacation rental in Winter
Captivating Views of Lake Chippewa from Three Level Chalet Cabin & Lake Home, vacation rental in Winter
Captivating Views of Lake Chippewa from Three Level Chalet Cabin & Lake Home, vacation rental in Winter

Captivating Views of Lake Chippewa from Three Level Chalet Cabin & Lake Home

Rental Home
8 bedrooms
5 bathrooms
Sleeps 19
Match: Sleeps
More info
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Cute cozy 2 bedroom cabin right on the water, vacation rental in Winter
Cute cozy 2 bedroom cabin right on the water, vacation rental in Winter
Cute cozy 2 bedroom cabin right on the water, vacation rental in Winter

Cute cozy 2 bedroom cabin right on the water

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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500' Lakeshore, 2 Docks Great Lake Views, Sand Beach, Sleeps 10, A/C, vacation rental in Winter
500' Lakeshore, 2 Docks Great Lake Views, Sand Beach, Sleeps 10, A/C, vacation rental in Winter
500' Lakeshore, 2 Docks Great Lake Views, Sand Beach, Sleeps 10, A/C, vacation rental in Winter

500' Lakeshore, 2 Docks Great Lake Views, Sand Beach, Sleeps 10, A/C

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Get away from it all- Cozy cabin in the woods lake access & private pier, vacation rental in Winter
Get away from it all- Cozy cabin in the woods lake access & private pier, vacation rental in Winter
Get away from it all- Cozy cabin in the woods lake access & private pier, vacation rental in Winter

Get away from it all- Cozy cabin in the woods lake access & private pier

Rental Home
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
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Find your Adventure at Lazy Moose Cabin on Beautiful Moose Lake/Wireless Int., vacation rental in Winter
Find your Adventure at Lazy Moose Cabin on Beautiful Moose Lake/Wireless Int., vacation rental in Winter
Find your Adventure at Lazy Moose Cabin on Beautiful Moose Lake/Wireless Int., vacation rental in Winter

Find your Adventure at Lazy Moose Cabin on Beautiful Moose Lake/Wireless Int.

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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New Listing! 4Br 2Ba Newly Renovated Cabin on Chippewa Flowage with Dock!, vacation rental in Winter
New Listing! 4Br 2Ba Newly Renovated Cabin on Chippewa Flowage with Dock!, vacation rental in Winter
New Listing! 4Br 2Ba Newly Renovated Cabin on Chippewa Flowage with Dock!, vacation rental in Winter

New Listing! 4Br 2Ba Newly Renovated Cabin on Chippewa Flowage with Dock!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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A Family Vacation is still Affordable, vacation rental in Winter
A Family Vacation is still Affordable, vacation rental in Winter
A Family Vacation is still Affordable, vacation rental in Winter

A Family Vacation is still Affordable

Rental Home
4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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PRIVATE CABIN ON CHIPPEWA FLOWAGE  (MOORES BAY). TROPICAL ATMOSPHERE, 100FT DOCK, vacation rental in Winter
PRIVATE CABIN ON CHIPPEWA FLOWAGE  (MOORES BAY). TROPICAL ATMOSPHERE, 100FT DOCK, vacation rental in Winter
PRIVATE CABIN ON CHIPPEWA FLOWAGE  (MOORES BAY). TROPICAL ATMOSPHERE, 100FT DOCK, vacation rental in Winter

PRIVATE CABIN ON CHIPPEWA FLOWAGE (MOORES BAY). TROPICAL ATMOSPHERE, 100FT DOCK

Rental Home
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Legendary Private Bar Awesome View Group Fun TV WIFI and wilderness beauty., vacation rental in Winter
Legendary Private Bar Awesome View Group Fun TV WIFI and wilderness beauty., vacation rental in Winter
Legendary Private Bar Awesome View Group Fun TV WIFI and wilderness beauty., vacation rental in Winter

Legendary Private Bar Awesome View Group Fun TV WIFI and wilderness beauty.

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage, vacation rental in Winter
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage, vacation rental in Winter
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage, vacation rental in Winter

2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Cozy Northwoods Getaway, vacation rental in Winter
Cozy Northwoods Getaway, vacation rental in Winter
Cozy Northwoods Getaway, vacation rental in Winter

Cozy Northwoods Getaway

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage, vacation rental in Winter
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage, vacation rental in Winter
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage, vacation rental in Winter

2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage, vacation rental in Winter
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage, vacation rental in Winter
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage, vacation rental in Winter

2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage, vacation rental in Winter
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage, vacation rental in Winter
2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage, vacation rental in Winter

2 Bedroom Lakeside Cabin-Family Fishing Resort-Hayward WI-Chippewa Flowage

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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House on 10 Acres Overlooking Chippewa River!, vacation rental in Winter
House on 10 Acres Overlooking Chippewa River!, vacation rental in Winter
House on 10 Acres Overlooking Chippewa River!, vacation rental in Winter

House on 10 Acres Overlooking Chippewa River!

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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#2Lakeside Cabin W/Beautiful Views Of Moose Lake ~ Private Dock with Boat launch, vacation rental in Winter
#2Lakeside Cabin W/Beautiful Views Of Moose Lake ~ Private Dock with Boat launch, vacation rental in Winter
#2Lakeside Cabin W/Beautiful Views Of Moose Lake ~ Private Dock with Boat launch, vacation rental in Winter

#2Lakeside Cabin W/Beautiful Views Of Moose Lake ~ Private Dock with Boat launch

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Huge Lake view-  -Sleeps 8-On Lake Chippewa, vacation rental in Winter
Huge Lake view-  -Sleeps 8-On Lake Chippewa, vacation rental in Winter
Huge Lake view-  -Sleeps 8-On Lake Chippewa, vacation rental in Winter

Huge Lake view- -Sleeps 8-On Lake Chippewa

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Exclusive Home On Chippewa Flowage- 3.6 acres with sand beach and two docks, vacation rental in Winter
Exclusive Home On Chippewa Flowage- 3.6 acres with sand beach and two docks, vacation rental in Winter
Exclusive Home On Chippewa Flowage- 3.6 acres with sand beach and two docks, vacation rental in Winter

Exclusive Home On Chippewa Flowage- 3.6 acres with sand beach and two docks

Rental Home
6 bedrooms
7 bathrooms
Sleeps 16
Match: Sleeps
More info
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Moose Lake, Hayward WI, vacation rental in Winter
Moose Lake, Hayward WI, vacation rental in Winter
Moose Lake, Hayward WI, vacation rental in Winter

Moose Lake, Hayward WI

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Cedar Tops Escape- on Lake Chippewa!  Fantastic Fishing!, vacation rental in Winter
Cedar Tops Escape- on Lake Chippewa!  Fantastic Fishing!, vacation rental in Winter
Cedar Tops Escape- on Lake Chippewa!  Fantastic Fishing!, vacation rental in Winter

Cedar Tops Escape- on Lake Chippewa! Fantastic Fishing!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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#1Lakeside Cabin W/Beautiful Views Of Moose Lake ~ Private Dock with Boat launch, vacation rental in Winter
#1Lakeside Cabin W/Beautiful Views Of Moose Lake ~ Private Dock with Boat launch, vacation rental in Winter
#1Lakeside Cabin W/Beautiful Views Of Moose Lake ~ Private Dock with Boat launch, vacation rental in Winter

#1Lakeside Cabin W/Beautiful Views Of Moose Lake ~ Private Dock with Boat launch

Rental Home
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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Ideal Private Northern Wisconsin Retreat on Flambeau River Sleeps 12, vacation rental in Winter
Ideal Private Northern Wisconsin Retreat on Flambeau River Sleeps 12, vacation rental in Winter
Ideal Private Northern Wisconsin Retreat on Flambeau River Sleeps 12, vacation rental in Winter

Ideal Private Northern Wisconsin Retreat on Flambeau River Sleeps 12

Rental Home
4 bedrooms
1 bathroom
Sleeps 12
Match: Sleeps
More info
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Affordable and comfortable lodging for rent , vacation rental in Winter
Affordable and comfortable lodging for rent , vacation rental in Winter
Affordable and comfortable lodging for rent , vacation rental in Winter

Affordable and comfortable lodging for rent

Rental Home
10 bedrooms
5 bathrooms
Sleeps 20
Match: Sleeps
More info
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Musky Joe's Twin Pines Resort, vacation rental in Winter
Musky Joe's Twin Pines Resort, vacation rental in Winter
Musky Joe's Twin Pines Resort, vacation rental in Winter

Musky Joe's Twin Pines Resort

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Two bedroom cabin right on the water, vacation rental in Winter
Two bedroom cabin right on the water, vacation rental in Winter
Two bedroom cabin right on the water, vacation rental in Winter

Two bedroom cabin right on the water

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Chief Lake Lodge Resort Cabin #8, vacation rental in Winter
Chief Lake Lodge Resort Cabin #8, vacation rental in Winter
Chief Lake Lodge Resort Cabin #8, vacation rental in Winter

Chief Lake Lodge Resort Cabin #8

Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Chippewa Flowage Luxury Cabin #9, vacation rental in Winter
Chippewa Flowage Luxury Cabin #9, vacation rental in Winter
Chippewa Flowage Luxury Cabin #9, vacation rental in Winter

Chippewa Flowage Luxury Cabin #9

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Tainter Cabins, vacation rental in Winter
Tainter Cabins, vacation rental in Winter
Tainter Cabins, vacation rental in Winter

Tainter Cabins

Rental Home
4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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Chippewa Flowage Luxury Cabin #11, vacation rental in Winter
Chippewa Flowage Luxury Cabin #11, vacation rental in Winter
Chippewa Flowage Luxury Cabin #11, vacation rental in Winter

Chippewa Flowage Luxury Cabin #11

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Cabin 3 bed 2 bath - Lake Chippewa-also known as the Chippewa Flowage-Hayward WI, vacation rental in Winter
Cabin 3 bed 2 bath - Lake Chippewa-also known as the Chippewa Flowage-Hayward WI, vacation rental in Winter
Cabin 3 bed 2 bath - Lake Chippewa-also known as the Chippewa Flowage-Hayward WI, vacation rental in Winter

Cabin 3 bed 2 bath - Lake Chippewa-also known as the Chippewa Flowage-Hayward WI

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Musky Bay Hideaway On The Chippewa Flowage - Lake Front, vacation rental in Winter
Musky Bay Hideaway On The Chippewa Flowage - Lake Front, vacation rental in Winter
Musky Bay Hideaway On The Chippewa Flowage - Lake Front, vacation rental in Winter

Musky Bay Hideaway On The Chippewa Flowage - Lake Front

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Buckhorn Lodge  - Lake Front, vacation rental in Winter
Buckhorn Lodge  - Lake Front, vacation rental in Winter
Buckhorn Lodge  - Lake Front, vacation rental in Winter

Buckhorn Lodge - Lake Front

Rental Home
8 bedrooms
5 bathrooms
Sleeps 19
Match: Sleeps
More info
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Chippewa View Lodge - Lake Front, vacation rental in Winter
Chippewa View Lodge - Lake Front, vacation rental in Winter
Chippewa View Lodge - Lake Front, vacation rental in Winter

Chippewa View Lodge - Lake Front

Rental Home
6 bedrooms
7 bathrooms
Sleeps 16
Match: Sleeps
More info
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Little House In The Big Woods - Lake Accress, vacation rental in Winter
Little House In The Big Woods - Lake Accress, vacation rental in Winter
Little House In The Big Woods - Lake Accress, vacation rental in Winter

Little House In The Big Woods - Lake Accress

Rental Home
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
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Chippewa Flowage Lake House - Lake Front, vacation rental in Winter
Chippewa Flowage Lake House - Lake Front, vacation rental in Winter
Chippewa Flowage Lake House - Lake Front, vacation rental in Winter

Chippewa Flowage Lake House - Lake Front

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Frequently Asked Questions about Winter