Vacation rentals in Winchester, WI

66 available vacation rental offers

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Best vacation rentals and Airbnb offers in Winchester, WI

The Loony Bin - Winchester, WI

The Loony Bin

Holiday Home, Winchester

The Loony Bin is a holiday home in Winchester. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

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About The Loony Bin

The Loony Bin is a holiday home in Winchester. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: ac, air conditioning, heating, and garden.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,021.

From$279/night
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Annabelle Log Home - Winchester, WI

Annabelle Log Home

Holiday Home, Winchester

Annabelle Log Home is a holiday home in Winchester, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Annabelle Log Home

Annabelle Log Home is a holiday home in Winchester, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, ac, air conditioning, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,066.

From$284/night
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Behnkes Bungalow - Winchester, WI

Behnkes Bungalow

Holiday Home, Winchester

Behnkes Bungalow is a holiday home in Winchester, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Behnkes Bungalow

Behnkes Bungalow is a holiday home in Winchester, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, ac, air conditioning, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,155.

From$284/night
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Sky Blue By The Bay - Winchester, WI

Sky Blue By The Bay

Holiday Home, Winchester

Sky Blue By The Bay is a holiday home in Winchester, with pet-friendly space and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Sky Blue By The Bay

Sky Blue By The Bay is a holiday home in Winchester, with pet-friendly space and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, ac, air conditioning, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,559.

From$316/night
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Vacation rentals with parking in Winchester, WI

Find vacation rentals that make arriving by car easier.

111 Two Queen Room with Woodland View - Winchester, WI

111 Two Queen Room with Woodland View

Apartment, Winchester

111 Two Queen Room with Woodland View is a apartment in Winchester, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About 111 Two Queen Room with Woodland View

111 Two Queen Room with Woodland View is a apartment in Winchester, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, parking, free parking, fireplace, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,332.

From$190/night
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112 Queen Room with easy access to Bike Trail - Winchester, WI

112 Queen Room with easy access to Bike Trail

Apartment, Winchester

112 Queen Room with easy access to Bike Trail is a apartment in Winchester, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About 112 Queen Room with easy access to Bike Trail

112 Queen Room with easy access to Bike Trail is a apartment in Winchester, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, parking, free parking, fireplace, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,332.

From$190/night
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113 Two Queen Room with Woodland View - Winchester, WI

113 Two Queen Room with Woodland View

Apartment, Winchester

113 Two Queen Room with Woodland View is a apartment in Winchester, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

Read more

About 113 Two Queen Room with Woodland View

113 Two Queen Room with Woodland View is a apartment in Winchester, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, parking, free parking, fireplace, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,332.

From$190/night
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Waterfront Mercer Cabin w/ Wraparound Porch! - Winchester, WI

Waterfront Mercer Cabin w/ Wraparound Porch!

Holiday Home, Winchester

Waterfront Mercer Cabin w/ Wraparound Porch! is a holiday home in Winchester, with easy beach access and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Waterfront Mercer Cabin w/ Wraparound Porch!

Waterfront Mercer Cabin w/ Wraparound Porch! is a holiday home in Winchester, with easy beach access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, parking, paid parking, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,091.

From$224/night
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Pet-friendly vacation rentals in Winchester, WI

Bring your pet along with stays that welcome four-legged travelers.

A dog friendly room with two queen beds, private bathroom, mini fridge, and single-serve coffee maker. - Winchester, WI

A dog friendly room with two queen beds, private bathroom, mini fridge, and single-serve coffee maker.

Apartment, Winchester

A dog friendly room with two queen beds, private bathroom, mini fridge, and single-serve coffee maker. is a apartment in Winchester, with pet-friendly space and parking. This stay gives…

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About A dog friendly room with two queen beds, private bathroom, mini fridge, and single-serve coffee maker.

A dog friendly room with two queen beds, private bathroom, mini fridge, and single-serve coffee maker. is a apartment in Winchester, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,332.

From$190/night
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A dog friendly room with two queen beds, private bathroom, mini fridge, and single-serve coffee maker. - Winchester, WI

A dog friendly room with two queen beds, private bathroom, mini fridge, and single-serve coffee maker.

Apartment, Winchester

A dog friendly room with two queen beds, private bathroom, mini fridge, and single-serve coffee maker. is a apartment in Winchester, with pet-friendly space and parking. This stay gives…

Read more

About A dog friendly room with two queen beds, private bathroom, mini fridge, and single-serve coffee maker.

A dog friendly room with two queen beds, private bathroom, mini fridge, and single-serve coffee maker. is a apartment in Winchester, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,332.

From$190/night
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A dog friendly room with two queen beds, private bathroom, mini fridge, and single-serve coffee maker. - Winchester, WI

A dog friendly room with two queen beds, private bathroom, mini fridge, and single-serve coffee maker.

Apartment, Winchester

A dog friendly room with two queen beds, private bathroom, mini fridge, and single-serve coffee maker. is a apartment in Winchester, with pet-friendly space and parking. This stay gives…

Read more

About A dog friendly room with two queen beds, private bathroom, mini fridge, and single-serve coffee maker.

A dog friendly room with two queen beds, private bathroom, mini fridge, and single-serve coffee maker. is a apartment in Winchester, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,332.

From$190/night
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Black Hawk @ Pine Noel Resort - Winchester, WI

Black Hawk @ Pine Noel Resort

Cabin, Winchester

Black Hawk @ Pine Noel Resort is a cabin in Winchester, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Black Hawk @ Pine Noel Resort

Black Hawk @ Pine Noel Resort is a cabin in Winchester, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,613.

From$230/night
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Vacation rentals with a kitchen in Winchester, WI

Compare stays with kitchen access for longer trips and easier meals.

Modern home , Great Retreat Nestled in the Beautiful Northwoods ...Adventures!<br> - Winchester, WI

Modern home , Great Retreat Nestled in the Beautiful Northwoods ...Adventures!<br>

Holiday Home, Winchester

Modern home , Great Retreat Nestled in the Beautiful Northwoods ...Adventures!<br> is a holiday home in Winchester, with pet-friendly space, parking, and kitchen access. This stay gives…

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About Modern home , Great Retreat Nestled in the Beautiful Northwoods ...Adventures!<br>

Modern home , Great Retreat Nestled in the Beautiful Northwoods ...Adventures!<br> is a holiday home in Winchester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,572.

From$225/night
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Mercer House on Major Snowmobile and ATV Trail - Winchester, WI

Mercer House on Major Snowmobile and ATV Trail

Holiday Home, Winchester

Mercer House on Major Snowmobile and ATV Trail is a holiday home in Winchester, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Mercer House on Major Snowmobile and ATV Trail

Mercer House on Major Snowmobile and ATV Trail is a holiday home in Winchester, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,917.

From$274/night
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Waterfront Mercer Cabin w/ Wraparound Porch! - Winchester, WI

Waterfront Mercer Cabin w/ Wraparound Porch!

Cabin, Winchester

Waterfront Mercer Cabin w/ Wraparound Porch! is a cabin in Winchester, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Waterfront Mercer Cabin w/ Wraparound Porch!

Waterfront Mercer Cabin w/ Wraparound Porch! is a cabin in Winchester, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,932.

From$276/night
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Lake home with about 300 ft of shoreline Rental Contract required before booking - Winchester, WI

Lake home with about 300 ft of shoreline Rental Contract required before booking

Holiday Home, Winchester

Lake home with about 300 ft of shoreline Rental Contract required before booking is a holiday home in Winchester, with easy beach access and kitchen access. This stay gives travelers a…

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About Lake home with about 300 ft of shoreline Rental Contract required before booking

Lake home with about 300 ft of shoreline Rental Contract required before booking is a holiday home in Winchester, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, beachfront, and beach front.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,115.

From$302/night
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Family-friendly vacation rentals in Winchester, WI

Plan a trip with stays that give families more room to spread out.

Lakefront 2-bedroom Cottage on Crystal Lake. Your perfect summer getaway. - Winchester, WI

Lakefront 2-bedroom Cottage on Crystal Lake. Your perfect summer getaway.

Cottage, Winchester

Lakefront 2-bedroom Cottage on Crystal Lake. Your perfect summer getaway. is a cottage in Winchester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a…

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About Lakefront 2-bedroom Cottage on Crystal Lake. Your perfect summer getaway.

Lakefront 2-bedroom Cottage on Crystal Lake. Your perfect summer getaway. is a cottage in Winchester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,395.

From$199/night
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Waterfront Mercer Cabin w/ Wraparound Porch! - Winchester, WI

Waterfront Mercer Cabin w/ Wraparound Porch!

Cottage, Winchester

Waterfront Mercer Cabin w/ Wraparound Porch! is a cottage in Winchester, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

Read more

About Waterfront Mercer Cabin w/ Wraparound Porch!

Waterfront Mercer Cabin w/ Wraparound Porch! is a cottage in Winchester, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,174.

From$261/night
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Lakefront Cabin #2 The Bluegill - Winchester, WI

Lakefront Cabin #2 The Bluegill

Cottage, Winchester

Lakefront Cabin #2 The Bluegill is a cottage in Winchester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Lakefront Cabin #2 The Bluegill

Lakefront Cabin #2 The Bluegill is a cottage in Winchester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,288.

From$327/night
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Lakefront Cabin #3 The Perch - Winchester, WI

Lakefront Cabin #3 The Perch

Cottage, Winchester

Lakefront Cabin #3 The Perch is a cottage in Winchester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Lakefront Cabin #3 The Perch

Lakefront Cabin #3 The Perch is a cottage in Winchester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,288.

From$327/night
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