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Winchester Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
15 rentals in Winchester.
Dog-friendly lakefront home with boat access, deck, fireplace, gas grill, kayaks, vacation rental in Winchester
Dog-friendly lakefront home with boat access, deck, fireplace, gas grill, kayaks, vacation rental in Winchester
Dog-friendly lakefront home with boat access, deck, fireplace, gas grill, kayaks, vacation rental in Winchester

Dog-friendly lakefront home with boat access, deck, fireplace, gas grill, kayaks

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Private Lakefront Cabin on North Turtle Lake, vacation rental in Winchester
Private Lakefront Cabin on North Turtle Lake, vacation rental in Winchester
Private Lakefront Cabin on North Turtle Lake, vacation rental in Winchester

Private Lakefront Cabin on North Turtle Lake

Rental Home
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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The Northwoods At Its Finest!, vacation rental in Winchester
The Northwoods At Its Finest!, vacation rental in Winchester
The Northwoods At Its Finest!, vacation rental in Winchester

The Northwoods At Its Finest!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lakeside Kitchenette - Feller, vacation rental in Winchester
Lakeside Kitchenette - Feller, vacation rental in Winchester
Lakeside Kitchenette - Feller, vacation rental in Winchester

Lakeside Kitchenette - Feller

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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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Lake Home Perfection!  Kayak I  Swim I  No Cleaning Fees, vacation rental in Winchester
Lake Home Perfection!  Kayak I  Swim I  No Cleaning Fees, vacation rental in Winchester
Lake Home Perfection!  Kayak I  Swim I  No Cleaning Fees, vacation rental in Winchester

Lake Home Perfection! Kayak I Swim I No Cleaning Fees

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lake Front, Private, Pet-friendly, Canoe Included! August weekends open! 3nt Min, vacation rental in Winchester
Lake Front, Private, Pet-friendly, Canoe Included! August weekends open! 3nt Min, vacation rental in Winchester
Lake Front, Private, Pet-friendly, Canoe Included! August weekends open! 3nt Min, vacation rental in Winchester

Lake Front, Private, Pet-friendly, Canoe Included! August weekends open! 3nt Min

Rental Home
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Secluded lakefront getaway with private dock, vacation rental in Winchester
Secluded lakefront getaway with private dock, vacation rental in Winchester
Secluded lakefront getaway with private dock, vacation rental in Winchester

Secluded lakefront getaway with private dock

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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NEW! Lakefront Paradise! Access to MANY Trails!, vacation rental in Winchester
NEW! Lakefront Paradise! Access to MANY Trails!, vacation rental in Winchester
NEW! Lakefront Paradise! Access to MANY Trails!, vacation rental in Winchester

NEW! Lakefront Paradise! Access to MANY Trails!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Woodland Wonderland | Spacious cabin-style house in Winchester with lake access, vacation rental in Winchester
Woodland Wonderland | Spacious cabin-style house in Winchester with lake access, vacation rental in Winchester
Woodland Wonderland | Spacious cabin-style house in Winchester with lake access, vacation rental in Winchester

Woodland Wonderland | Spacious cabin-style house in Winchester with lake access

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Dog-friendly, lakefront home with a wood fireplace, decks, dock, & AC, vacation rental in Winchester
Dog-friendly, lakefront home with a wood fireplace, decks, dock, & AC, vacation rental in Winchester
Dog-friendly, lakefront home with a wood fireplace, decks, dock, & AC, vacation rental in Winchester

Dog-friendly, lakefront home with a wood fireplace, decks, dock, & AC

Rental Home
3 bedrooms
3 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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Full hotel with bar, commercial kitchen, pool table & fireplaces - dog-friendly, vacation rental in Winchester
Full hotel with bar, commercial kitchen, pool table & fireplaces - dog-friendly, vacation rental in Winchester
Full hotel with bar, commercial kitchen, pool table & fireplaces - dog-friendly, vacation rental in Winchester

Full hotel with bar, commercial kitchen, pool table & fireplaces - dog-friendly

Rental Home
6 bedrooms
4 bathrooms
Sleeps 28
Match: Sleeps
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Sportsman’s Resort, vacation rental in Winchester
Sportsman’s Resort, vacation rental in Winchester
Sportsman’s Resort, vacation rental in Winchester

Sportsman’s Resort

Rental Home
5 bedrooms
6 bathrooms
Sleeps 5
Match: Sleeps
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Turtle Point Retreat, vacation rental in Winchester
Turtle Point Retreat, vacation rental in Winchester
Turtle Point Retreat, vacation rental in Winchester

Turtle Point Retreat

Rental Home
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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