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Winter Holiday Rentals

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50 rentals in Winter.
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Newly Built - Second Season Renting!  Luxury Getaway in a Tranquil Setting, holiday rental in Winter

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

3 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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Great 4 Season Family Getaway!  Quiet, yet full of Fun!, holiday rental in Winter

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

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

Private Modern Home in Rustic Surroundings and Much to Do

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Bring the Family to our Wonderful Log Cabin on Connors Lake!, holiday rental in Winter

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

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful 3 bedroom lake home near Winter, Wisconsin., holiday rental in Winter

Beautiful 3 bedroom lake home near Winter, Wisconsin.

3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Up North Cabin with Pontoon. Winter Ice Fishing and Snowmobiling Trails., holiday rental in Winter

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

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

Bears Den on Private Lake

5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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NEW! Inviting Wisconsin Cottage w/ Charcoal Grill!, holiday rental in Winter

NEW! Inviting Wisconsin Cottage w/ Charcoal Grill!

2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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NEW! Wisconsin Community Cottage w/ Charcoal Grill, holiday rental in Winter

NEW! Wisconsin Community Cottage w/ Charcoal Grill

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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NEW! Cozy Pet-Friendly Winter Cottage in Community, holiday rental in Winter

NEW! Cozy Pet-Friendly Winter Cottage in Community

2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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NEW! Community Winter Cottage w/ Shared Amenities!, holiday rental in Winter

NEW! Community Winter Cottage w/ Shared Amenities!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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*Hipp's Hideaway -- Looking for a Serene Get Away for Thx, Xmas or New Years ?, holiday rental in Winter

*Hipp's Hideaway -- Looking for a Serene Get Away for Thx, Xmas or New Years ?

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Snowmobile on the famous Chippewa Flowage in Hayward, WI, holiday rental in Winter

Snowmobile on the famous Chippewa Flowage in Hayward, WI

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Super Private...Amazing Views...Quiet Solitude!!, holiday rental in Winter

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

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Secluded Nostalgic Lodge, Room for All, Sandy Shore,Teal Lake  Hayward, WI, holiday rental in Winter

Secluded Nostalgic Lodge, Room for All, Sandy Shore,Teal Lake Hayward, WI

7 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Northern Comfort on Lovejoy Lake, Hayward, WI, holiday rental in Winter

Northern Comfort on Lovejoy Lake, Hayward, WI

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Private Lake Home On the Beautiful Tiger Cat! Pontoon Included for Summer weeks, holiday rental in Winter

Private Lake Home On the Beautiful Tiger Cat! Pontoon Included for Summer weeks

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful Vacation Rental - Real Hand Scribed Log Home on Lovejoy Lake, holiday rental in Winter

Beautiful Vacation Rental - Real Hand Scribed Log Home on Lovejoy Lake

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Ice Fish & Snowmobile on the Famous Chippewa Flowage in Hayward, WI, holiday rental in Winter

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

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Secluded Hayward Cabin, holiday rental in Winter

Secluded Hayward Cabin

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Summer in Winter (Unit 6), holiday rental in Winter

Summer in Winter (Unit 6)

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Summer in Winter (Unit 5), holiday rental in Winter

Summer in Winter (Unit 5)

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Private Secluded Log Home, holiday rental in Winter

Private Secluded Log Home

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Lakefront Cabin on the Chippewa Flowage Near Hayward, Wisconsin, holiday rental in Winter

Lakefront Cabin on the Chippewa Flowage Near Hayward, Wisconsin

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Outdoor Enthusiasts Paradise!  Fishing, Snowmobiling And Four-Wheeling ..., holiday rental in Winter

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

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Rustic and Charming one Bedroom cabin., holiday rental in Winter

Rustic and Charming one Bedroom cabin.

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Cute cozy 2 bedroom cabin right on the water, holiday rental in Winter

Cute cozy 2 bedroom cabin right on the water

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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500' Lakeshore, 2 Docks Great Lake Views, Sand Beach, Sleeps 10, A/C, holiday rental in Winter

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

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Find your Adventure at Lazy Moose Cabin on Beautiful Moose Lake/Wireless Int., holiday rental in Winter

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

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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A Family Vacation is still Affordable, holiday rental in Winter

A Family Vacation is still Affordable

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

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

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Private Hayward  Log Cabin Lodge, Secluded, 3 Docks, 8 acres Endless Shoreline, holiday rental in Winter

Private Hayward Log Cabin Lodge, Secluded, 3 Docks, 8 acres Endless Shoreline

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Clear Lake Point - log cabin on private peninsula, holiday rental in Winter

Clear Lake Point - log cabin on private peninsula

4 bedrooms
2 bathrooms
Sleeps 17
Match: Sleeps
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Legendary Private Bar Awesome View Group Fun TV WIFI and wilderness beauty., holiday rental in Winter

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

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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K&K's Lakeside Lodge-Hayward Relaxing Getaway, holiday rental in Winter

K&K's Lakeside Lodge-Hayward Relaxing Getaway

3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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3 BEDROOMS • 2 BATHROOM • SLEEPS 8, holiday rental in Winter

3 BEDROOMS • 2 BATHROOM • SLEEPS 8

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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3 BEDROOMS • 1.5 BATHROOM • SLEEPS 8, holiday rental in Winter

3 BEDROOMS • 1.5 BATHROOM • SLEEPS 8

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Butler's Bay Teal Lake Cabin, holiday rental in Winter

Butler's Bay Teal Lake Cabin

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Log Home On Lake Chippewa 3 bed 2 bath Eaglesnest, holiday rental in Winter

Log Home On Lake Chippewa 3 bed 2 bath Eaglesnest

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Moose Lake, Hayward WI, holiday rental in Winter

Moose Lake, Hayward WI

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Affordable and comfortable lodging for rent, holiday rental in Winter

Affordable and comfortable lodging for rent

10 bedrooms
5 bathrooms
Sleeps 20
Match: Sleeps
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Located on Round Lake, holiday rental in Winter

Located on Round Lake

3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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3 BEDROOMS • 2 BATHROOM • SLEEPS 8, holiday rental in Winter

3 BEDROOMS • 2 BATHROOM • SLEEPS 8

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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3 BEDROOMS • 1.5 BATHROOM • SLEEPS 8, holiday rental in Winter

3 BEDROOMS • 1.5 BATHROOM • SLEEPS 8

3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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3 BEDROOMS • 2 BATHROOM • SLEEPS 8, holiday rental in Winter

3 BEDROOMS • 2 BATHROOM • SLEEPS 8

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Lakefront Hayward Home w/ Fire Pit by Ski Trails!, holiday rental in Winter

Lakefront Hayward Home w/ Fire Pit by Ski Trails!

3 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Butler's Bay Teal Lake Cabin, holiday rental in Winter

Butler's Bay Teal Lake Cabin

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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House on 10 Acres Overlooking Chippewa River!, holiday rental in Winter

House on 10 Acres Overlooking Chippewa River!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Cheif Lake Lodge, holiday rental in Winter

Cheif Lake Lodge

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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