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Winchester Vacation Rentals

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50 rentals in Winchester.
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Winchester Lake House on 900+ acre Turtle Lake Chain

Rental Home
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Lovingly restored, historic home on 160 acres w/ game room & dock!, vacation rental in Winchester
Lovingly restored, historic home on 160 acres w/ game room & dock!, vacation rental in Winchester
Lovingly restored, historic home on 160 acres w/ game room & dock!, vacation rental in Winchester

Lovingly restored, historic home on 160 acres w/ game room & dock!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Secluded lakefront getaway with private dock

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Fully Remodeled Chain Of Lakes Home, vacation rental in Winchester
Fully Remodeled Chain Of Lakes Home, vacation rental in Winchester
Fully Remodeled Chain Of Lakes Home, vacation rental in Winchester

Fully Remodeled Chain Of Lakes Home

Rental Home
3 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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New listing! Spacious, lakefront dream home w/ a deck, firepit, & private dock, vacation rental in Winchester
New listing! Spacious, lakefront dream home w/ a deck, firepit, & private dock, vacation rental in Winchester
New listing! Spacious, lakefront dream home w/ a deck, firepit, & private dock, vacation rental in Winchester

New listing! Spacious, lakefront dream home w/ a deck, firepit, & private dock

Rental Home
5 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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Fully furnished log home in one of northern Wisconsin's last wilderness areas

Rental Home
4 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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Beautiful Executive Lake Home on Peninsula with 657 ft Lake Frontage, vacation rental in Winchester
Beautiful Executive Lake Home on Peninsula with 657 ft Lake Frontage, vacation rental in Winchester
Beautiful Executive Lake Home on Peninsula with 657 ft Lake Frontage, vacation rental in Winchester

Beautiful Executive Lake Home on Peninsula with 657 ft Lake Frontage

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Lake Front Home, Private Pier, On Snowmobile Trail w/ Trailer Parking

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Lakefront home on Discovery Center grounds w/ dock, kayaks & canoes, vacation rental in Winchester
Lakefront home on Discovery Center grounds w/ dock, kayaks & canoes, vacation rental in Winchester
Lakefront home on Discovery Center grounds w/ dock, kayaks & canoes, vacation rental in Winchester

Lakefront home on Discovery Center grounds w/ dock, kayaks & canoes

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Time to start planning your summer ATV trip!, vacation rental in Winchester
Time to start planning your summer ATV trip!, vacation rental in Winchester
Time to start planning your summer ATV trip!, vacation rental in Winchester

Time to start planning your summer ATV trip!

Rental Home
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Northwoods Hideaway On Crystal Clear Private Carlin Lake, vacation rental in Winchester
Northwoods Hideaway On Crystal Clear Private Carlin Lake, vacation rental in Winchester
Northwoods Hideaway On Crystal Clear Private Carlin Lake, vacation rental in Winchester

Northwoods Hideaway On Crystal Clear Private Carlin Lake

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Cozy Cottage on Grand Portage Lake, Right on ATV and Snowmobile Trail!, vacation rental in Winchester
Cozy Cottage on Grand Portage Lake, Right on ATV and Snowmobile Trail!, vacation rental in Winchester
Cozy Cottage on Grand Portage Lake, Right on ATV and Snowmobile Trail!, vacation rental in Winchester

Cozy Cottage on Grand Portage Lake, Right on ATV and Snowmobile Trail!

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Newer pet friendly lake home with 4 bedrooms and 3 baths, vacation rental in Winchester
Newer pet friendly lake home with 4 bedrooms and 3 baths, vacation rental in Winchester
Newer pet friendly lake home with 4 bedrooms and 3 baths, vacation rental in Winchester

Newer pet friendly lake home with 4 bedrooms and 3 baths

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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BIRCH BRAE- spectacular house on Big Lake for an amazing Northwoods experience!, vacation rental in Winchester
BIRCH BRAE- spectacular house on Big Lake for an amazing Northwoods experience!, vacation rental in Winchester
BIRCH BRAE- spectacular house on Big Lake for an amazing Northwoods experience!, vacation rental in Winchester

BIRCH BRAE- spectacular house on Big Lake for an amazing Northwoods experience!

Rental Home
7 bedrooms
4 bathrooms
Sleeps 20
Match: Sleeps
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Lakefront home w/ furnished deck, firepit & private dock - dogs OK!, vacation rental in Winchester
Lakefront home w/ furnished deck, firepit & private dock - dogs OK!, vacation rental in Winchester
Lakefront home w/ furnished deck, firepit & private dock - dogs OK!, vacation rental in Winchester

Lakefront home w/ furnished deck, firepit & private dock - dogs OK!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Private & Quaint Cabin in Mercer.  Close To Town With Many Northwoods Amenities., vacation rental in Winchester
Private & Quaint Cabin in Mercer.  Close To Town With Many Northwoods Amenities., vacation rental in Winchester
Private & Quaint Cabin in Mercer.  Close To Town With Many Northwoods Amenities., vacation rental in Winchester

Private & Quaint Cabin in Mercer. Close To Town With Many Northwoods Amenities.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Gorgeous dog-friendly home w/ a full kitchen, outdoor fire pit with lake view

Rental Home
4 bedrooms
5 bathrooms
Sleeps 15
Match: Sleeps
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Private lakefront home w/ boat dock, fireplace, large yard - dogs welcome!, vacation rental in Winchester
Private lakefront home w/ boat dock, fireplace, large yard - dogs welcome!, vacation rental in Winchester
Private lakefront home w/ boat dock, fireplace, large yard - dogs welcome!, vacation rental in Winchester

Private lakefront home w/ boat dock, fireplace, large yard - dogs welcome!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Newly Remodeled Condo on Manitowish Lake With Amazing Lake Views, vacation rental in Winchester
Newly Remodeled Condo on Manitowish Lake With Amazing Lake Views, vacation rental in Winchester
Newly Remodeled Condo on Manitowish Lake With Amazing Lake Views, vacation rental in Winchester

Newly Remodeled Condo on Manitowish Lake With Amazing Lake Views

Condo/Apartment
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Newly remodeled lake home w/panoramic views & private swimming area, vacation rental in Winchester
Newly remodeled lake home w/panoramic views & private swimming area, vacation rental in Winchester
Newly remodeled lake home w/panoramic views & private swimming area, vacation rental in Winchester

Newly remodeled lake home w/panoramic views & private swimming area

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Your Up North getaway, vacation rental in Winchester
Your Up North getaway, vacation rental in Winchester
Your Up North getaway, vacation rental in Winchester

Your Up North getaway

Rental Home
4 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Adorable Remodeled Cabin on Manitowish Lake--Amazing Views!, vacation rental in Winchester
Adorable Remodeled Cabin on Manitowish Lake--Amazing Views!, vacation rental in Winchester
Adorable Remodeled Cabin on Manitowish Lake--Amazing Views!, vacation rental in Winchester

Adorable Remodeled Cabin on Manitowish Lake--Amazing Views!

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Luxury lakefront home w/ private dock, beach access, kayaks & bikes, vacation rental in Winchester
Luxury lakefront home w/ private dock, beach access, kayaks & bikes, vacation rental in Winchester
Luxury lakefront home w/ private dock, beach access, kayaks & bikes, vacation rental in Winchester

Luxury lakefront home w/ private dock, beach access, kayaks & bikes

Rental Home
4 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
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Beautiful location with large private dock and in house sauna, vacation rental in Winchester
Beautiful location with large private dock and in house sauna, vacation rental in Winchester
Beautiful location with large private dock and in house sauna, vacation rental in Winchester

Beautiful location with large private dock and in house sauna

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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New listing! Dog-friendly lake home w/ dock, boat, kayaks, a canoe & fireplace!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Premium Cleaned | Family-friendly getaway w/ sauna, bunkhouse, & private dock -, vacation rental in Winchester
Premium Cleaned | Family-friendly getaway w/ sauna, bunkhouse, & private dock -, vacation rental in Winchester
Premium Cleaned | Family-friendly getaway w/ sauna, bunkhouse, & private dock -, vacation rental in Winchester

Premium Cleaned | Family-friendly getaway w/ sauna, bunkhouse, & private dock -

Rental Home
4 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Secluded Lakefront House with Heated Garage, 21-Foot Pontoon Boat Included!, vacation rental in Winchester
Secluded Lakefront House with Heated Garage, 21-Foot Pontoon Boat Included!, vacation rental in Winchester
Secluded Lakefront House with Heated Garage, 21-Foot Pontoon Boat Included!, vacation rental in Winchester

Secluded Lakefront House with Heated Garage, 21-Foot Pontoon Boat Included!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Welcome to “Mani Bay Chalet”, vacation rental in Winchester
Welcome to “Mani Bay Chalet”, vacation rental in Winchester
Welcome to “Mani Bay Chalet”, vacation rental in Winchester

Welcome to “Mani Bay Chalet”

Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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New listing! Cozy lake cabin with access to lakefront pier & community firepit!, vacation rental in Winchester
New listing! Cozy lake cabin with access to lakefront pier & community firepit!, vacation rental in Winchester
New listing! Cozy lake cabin with access to lakefront pier & community firepit!, vacation rental in Winchester

New listing! Cozy lake cabin with access to lakefront pier & community firepit!

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Beautiful location on Little Star Lake and the 10 lake Manitowish Chain, vacation rental in Winchester
Beautiful location on Little Star Lake and the 10 lake Manitowish Chain, vacation rental in Winchester
Beautiful location on Little Star Lake and the 10 lake Manitowish Chain, vacation rental in Winchester

Beautiful location on Little Star Lake and the 10 lake Manitowish Chain

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Beautiful Lakefront Cabin with a Private Dock, Firepit, and Large Yard!, vacation rental in Winchester
Beautiful Lakefront Cabin with a Private Dock, Firepit, and Large Yard!, vacation rental in Winchester
Beautiful Lakefront Cabin with a Private Dock, Firepit, and Large Yard!, vacation rental in Winchester

Beautiful Lakefront Cabin with a Private Dock, Firepit, and Large Yard!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Cabin on Manitowish Chain, vacation rental in Winchester
Cozy Cabin on Manitowish Chain, vacation rental in Winchester
Cozy Cabin on Manitowish Chain, vacation rental in Winchester

Cozy Cabin on Manitowish Chain

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Classic Up North Cabin on Big Lake, vacation rental in Winchester
Classic Up North Cabin on Big Lake, vacation rental in Winchester
Classic Up North Cabin on Big Lake, vacation rental in Winchester

Classic Up North Cabin on Big Lake

Rental Home
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
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New listing! Lakefront home with private dock, vacation rental in Winchester
New listing! Lakefront home with private dock, vacation rental in Winchester
New listing! Lakefront home with private dock, vacation rental in Winchester

New listing! Lakefront home with private dock

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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New listing! Dog-friendly lake home w/private dock/campfire pit/sauna/free WiFi!, vacation rental in Winchester
New listing! Dog-friendly lake home w/private dock/campfire pit/sauna/free WiFi!, vacation rental in Winchester
New listing! Dog-friendly lake home w/private dock/campfire pit/sauna/free WiFi!, vacation rental in Winchester

New listing! Dog-friendly lake home w/private dock/campfire pit/sauna/free WiFi!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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In-town lodge steps from lake, snowmobile trails, fishing, boating, much more!, vacation rental in Winchester
In-town lodge steps from lake, snowmobile trails, fishing, boating, much more!, vacation rental in Winchester
In-town lodge steps from lake, snowmobile trails, fishing, boating, much more!, vacation rental in Winchester

In-town lodge steps from lake, snowmobile trails, fishing, boating, much more!

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Vacation/Fisherman's Cottage, vacation rental in Winchester
Vacation/Fisherman's Cottage, vacation rental in Winchester
Vacation/Fisherman's Cottage, vacation rental in Winchester

Vacation/Fisherman's Cottage

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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New Family Friendly Vacation Home On Presque Isle Chain-Of-Lakes In Northern WI, vacation rental in Winchester
New Family Friendly Vacation Home On Presque Isle Chain-Of-Lakes In Northern WI, vacation rental in Winchester
New Family Friendly Vacation Home On Presque Isle Chain-Of-Lakes In Northern WI, vacation rental in Winchester

New Family Friendly Vacation Home On Presque Isle Chain-Of-Lakes In Northern WI

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Silent Sport Getaway- only steps away from 50+ miles of bike trails

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Secluded lakefront home on 10 lake chain with private dock and swimming, vacation rental in Winchester
Secluded lakefront home on 10 lake chain with private dock and swimming, vacation rental in Winchester
Secluded lakefront home on 10 lake chain with private dock and swimming, vacation rental in Winchester

Secluded lakefront home on 10 lake chain with private dock and swimming

Rental Home
5 bedrooms
5 bathrooms
Sleeps 18
Match: Sleeps
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New listing! Lakefront home with fireplace, dock, & canoe - dog-friendly!, vacation rental in Winchester
New listing! Lakefront home with fireplace, dock, & canoe - dog-friendly!, vacation rental in Winchester
New listing! Lakefront home with fireplace, dock, & canoe - dog-friendly!, vacation rental in Winchester

New listing! Lakefront home with fireplace, dock, & canoe - dog-friendly!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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North woods retreat., vacation rental in Winchester
North woods retreat., vacation rental in Winchester
North woods retreat., vacation rental in Winchester

North woods retreat.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Luxurious Lakeside Getaway, vacation rental in Winchester
Luxurious Lakeside Getaway, vacation rental in Winchester
Luxurious Lakeside Getaway, vacation rental in Winchester

Luxurious Lakeside Getaway

Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Lakefront Cabin #4 The Crappie, vacation rental in Winchester
Lakefront Cabin #4 The Crappie, vacation rental in Winchester
Lakefront Cabin #4 The Crappie, vacation rental in Winchester

Lakefront Cabin #4 The Crappie

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Lakefront Cabin #8 The Musky House, vacation rental in Winchester
Lakefront Cabin #8 The Musky House, vacation rental in Winchester
Lakefront Cabin #8 The Musky House, vacation rental in Winchester

Lakefront Cabin #8 The Musky House

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lakefront Cabin #5 The Bass, vacation rental in Winchester
Lakefront Cabin #5 The Bass, vacation rental in Winchester
Lakefront Cabin #5 The Bass, vacation rental in Winchester

Lakefront Cabin #5 The Bass

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Family-Friendly Lake House ~ No Extra Fees For All 10 Guests ~ EXCELLENT VALUE!, vacation rental in Winchester
Family-Friendly Lake House ~ No Extra Fees For All 10 Guests ~ EXCELLENT VALUE!, vacation rental in Winchester
Family-Friendly Lake House ~ No Extra Fees For All 10 Guests ~ EXCELLENT VALUE!, vacation rental in Winchester

Family-Friendly Lake House ~ No Extra Fees For All 10 Guests ~ EXCELLENT VALUE!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Lake Cottage Northern Wisconsin, Mercer, vacation rental in Winchester
Lake Cottage Northern Wisconsin, Mercer, vacation rental in Winchester
Lake Cottage Northern Wisconsin, Mercer, vacation rental in Winchester

Lake Cottage Northern Wisconsin, Mercer

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Semi-Secluded Escape on Bike/Snowmobile Trails - Near Lakes & Town!, vacation rental in Winchester
Semi-Secluded Escape on Bike/Snowmobile Trails - Near Lakes & Town!, vacation rental in Winchester
Semi-Secluded Escape on Bike/Snowmobile Trails - Near Lakes & Town!, vacation rental in Winchester

Semi-Secluded Escape on Bike/Snowmobile Trails - Near Lakes & Town!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Long Lake Rustic Nature Lover Retreat, vacation rental in Winchester
Long Lake Rustic Nature Lover Retreat, vacation rental in Winchester
Long Lake Rustic Nature Lover Retreat, vacation rental in Winchester

Long Lake Rustic Nature Lover Retreat

Rental Home
4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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