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Winchester Holiday Rentals

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

Winchester Lake House on 900+ acre Turtle Lake Chain

2 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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Lovingly restored, historic home on 160 acres w/ game room & dock!, holiday rental in Winchester

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

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Secluded lakefront getaway with private dock, holiday rental in Winchester

Secluded lakefront getaway with private dock

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

Fully Remodeled Chain Of Lakes Home

3 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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Beautiful Executive Lake Home on Peninsula with 657 ft Lake Frontage, holiday rental in Winchester

Beautiful Executive Lake Home on Peninsula with 657 ft Lake Frontage

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Lakefront home on Discovery Center grounds w/ dock, kayaks & canoes, holiday rental in Winchester

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

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Northwoods Hideaway On Crystal Clear Private Carlin Lake, holiday rental in Winchester

Northwoods Hideaway On Crystal Clear Private Carlin Lake

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Beautiful Lake Front Home, Private Pier, On Snowmobile Trail w/ Trailer Parking, holiday rental in Winchester

Beautiful Lake Front Home, Private Pier, On Snowmobile Trail w/ Trailer Parking

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Snowmobile Season Is Coming, holiday rental in Winchester

Snowmobile Season Is Coming

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Time to start planning your summer ATV trip!, holiday rental in Winchester

Time to start planning your summer ATV trip!

3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Snowmobilers & Skiers Full Scandinavian Log Home On Private Lake, holiday rental in Winchester

Snowmobilers & Skiers Full Scandinavian Log Home On Private Lake

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Newer pet friendly lake home with 4 bedrooms and 3 baths, holiday rental in Winchester

Newer pet friendly lake home with 4 bedrooms and 3 baths

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Lakefront home w/ furnished deck, firepit & private dock - dogs OK!, holiday rental in Winchester

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

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

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

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Cottage on Grand Portage Lake, Right on ATV and Snowmobile Trail!, holiday rental in Winchester

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

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Gorgeous dog-friendly home w/ a full kitchen, outdoor fire pit with lake view, holiday rental in Winchester

Gorgeous dog-friendly home w/ a full kitchen, outdoor fire pit with lake view

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

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

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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New listing! Peaceful cottage on Oxbow Lake w/ trail access, firepit & kayak!, holiday rental in Winchester

New listing! Peaceful cottage on Oxbow Lake w/ trail access, firepit & kayak!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Full Log Home On Private Lake Close To Town, Snowmobile Trails, & Golf Course, holiday rental in Winchester

Full Log Home On Private Lake Close To Town, Snowmobile Trails, & Golf Course

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Newly remodeled lake home w/panoramic views & private swimming area, holiday rental in Winchester

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

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful Cabin at Aberdeen Lodge on Manitowish Chain, holiday rental in Winchester

Beautiful Cabin at Aberdeen Lodge on Manitowish Chain

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Premium Cleaned | Family-friendly getaway w/ sauna, bunkhouse, & private dock -, holiday rental in Winchester

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

5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Classic Wisconsin up-north cottage on the premier Manitowish Chain of Lakes., holiday rental in Winchester

Classic Wisconsin up-north cottage on the premier Manitowish Chain of Lakes.

2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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New listing! Dog-friendly lake home w/ dock, boat, kayaks, a canoe & fireplace!, holiday rental in Winchester

New listing! Dog-friendly lake home w/ dock, boat, kayaks, a canoe & fireplace!

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Lakefront Cabin #1 The Sunfish, holiday rental in Winchester

Lakefront Cabin #1 The Sunfish

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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New listing! Cozy lake cabin with access to lakefront pier & community firepit!, holiday rental in Winchester

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

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Dog-friendly lakefront cabin w/wood fireplace, patio & firepit - kayaks & canoe!, holiday rental in Winchester

Dog-friendly lakefront cabin w/wood fireplace, patio & firepit - kayaks & canoe!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful location on Little Star Lake and the 10 lake Manitowish Chain, holiday rental in Winchester

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

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Watefront Villa - Great Private Location, Pontoon Included in Peak Season!, holiday rental in Winchester

Watefront Villa - Great Private Location, Pontoon Included in Peak Season!

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful Lakefront Cabin with a Private Dock, Firepit, and Large Yard!, holiday rental in Winchester

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

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Classic Up North Cabin on Big Lake, holiday rental in Winchester

Classic Up North Cabin on Big Lake

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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New listing! Lakefront home with private dock, holiday rental in Winchester

New listing! Lakefront home with private dock

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

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

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

Vacation/Fisherman's Cottage

2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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New Family Friendly Vacation Home On Presque Isle Chain-Of-Lakes In Northern WI, holiday rental in Winchester

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

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Silent Sport Getaway- only steps away from 50+ miles of bike trails, holiday rental in Winchester

Silent Sport Getaway- only steps away from 50+ miles of bike trails

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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New listing! Lakefront home with fireplace, dock, & canoe - dog-friendly!, holiday rental in Winchester

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

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lakefront Cabin #3 The Perch, holiday rental in Winchester

Lakefront Cabin #3 The Perch

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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North woods retreat., holiday rental in Winchester

North woods retreat.

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lakefront Cabin #2 The Bluegill, holiday rental in Winchester

Lakefront Cabin #2 The Bluegill

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Lakefront Cabin #4 The Crappie, holiday rental in Winchester

Lakefront Cabin #4 The Crappie

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Lakefront Winchester Cabin w/ Deck, Grill & Dock!, holiday rental in Winchester

Lakefront Winchester Cabin w/ Deck, Grill & Dock!

1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
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Winchester Condo on South Turtle Lake w/Boat Slip!, holiday rental in Winchester

Winchester Condo on South Turtle Lake w/Boat Slip!

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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South Turtle Lake Studio w/Fishing Pier & Fire Pit, holiday rental in Winchester

South Turtle Lake Studio w/Fishing Pier & Fire Pit

0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Fishermans Studio on South Turtle Lake w/Boat Slip, holiday rental in Winchester

Fishermans Studio on South Turtle Lake w/Boat Slip

0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Lakefront Cabin #8 The Musky House, holiday rental in Winchester

Lakefront Cabin #8 The Musky House

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lakefront Cabin #5 The Bass, holiday rental in Winchester

Lakefront Cabin #5 The Bass

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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NEW! Stunning Presque Isle Home: Deck + Boat Dock, holiday rental in Winchester

NEW! Stunning Presque Isle Home: Deck + Boat Dock

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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NEW! Waterfront Mercer Cabin w/ Wraparound Porch!, holiday rental in Winchester

NEW! Waterfront Mercer Cabin w/ Wraparound Porch!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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NEW! Cozy Lakefront Cabin w/ Indoor Gas Fireplace!, holiday rental in Winchester

NEW! Cozy Lakefront Cabin w/ Indoor Gas Fireplace!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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