Vacation rentals in Sheboygan, WI

32 available vacation rental offers

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Best Vacation rentals and Airbnb offers in Sheboygan, WI

Private Guest Bedroom - 2E East Room - Close to Lake Michigan - Sheboygan, WI

Private Guest Bedroom - 2E East Room - Close to Lake Michigan

Homestay, Sheboygan

Private Guest Bedroom - 2E East Room - Close to Lake Michigan is a homestay in Sheboygan, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base…

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About Private Guest Bedroom - 2E East Room - Close to Lake Michigan

Private Guest Bedroom - 2E East Room - Close to Lake Michigan is a homestay in Sheboygan, with parking, kitchen access, and room for a group. 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, parking, and paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $516.

From$44/night
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2 Mi to Dtwn: Studio Suite in Sheboygan - Sheboygan, WI

2 Mi to Dtwn: Studio Suite in Sheboygan

Apartment, Sheboygan

2 Mi to Dtwn: Studio Suite in Sheboygan is a apartment in Sheboygan, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About 2 Mi to Dtwn: Studio Suite in Sheboygan

2 Mi to Dtwn: Studio Suite in Sheboygan is a apartment in Sheboygan, 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 $1,028.

From$80/night
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Dtwn Sheboygan Apt Above Local Bar! - Sheboygan, WI

Dtwn Sheboygan Apt Above Local Bar!

Apartment, Sheboygan

Dtwn Sheboygan Apt Above Local Bar! is a apartment in Sheboygan, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Dtwn Sheboygan Apt Above Local Bar!

Dtwn Sheboygan Apt Above Local Bar! is a apartment in Sheboygan, 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 cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,488.

From$110/night
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2 Mi to Dtwn: Studio Suite in Sheboygan - Sheboygan, WI

2 Mi to Dtwn: Studio Suite in Sheboygan

Apartment, Sheboygan

2 Mi to Dtwn: Studio Suite in Sheboygan is a apartment in Sheboygan, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About 2 Mi to Dtwn: Studio Suite in Sheboygan

2 Mi to Dtwn: Studio Suite in Sheboygan is a apartment in Sheboygan, 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: free cancellation, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,095.

From$127/night
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Best Sheboygan, WI vacation rentals with parking

Find vacation rentals that make arriving by car easier.

At River's Edge - Charming 2BR River Retreat with Garage - Sheboygan, WI

At River's Edge - Charming 2BR River Retreat with Garage

Holiday Home, Sheboygan

At River's Edge - Charming 2BR River Retreat with Garage is a holiday home in Sheboygan, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About At River's Edge - Charming 2BR River Retreat with Garage

At River's Edge - Charming 2BR River Retreat with Garage is a holiday home in Sheboygan, with parking, kitchen access, and room for a group. 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 $2,378.

From$251/night
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BEACHSIDE GETAWAY IN SHEBOYGAN - Sheboygan, WI

BEACHSIDE GETAWAY IN SHEBOYGAN

Condo, Sheboygan

BEACHSIDE GETAWAY IN SHEBOYGAN is a condo in Sheboygan, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About BEACHSIDE GETAWAY IN SHEBOYGAN

BEACHSIDE GETAWAY IN SHEBOYGAN is a condo in Sheboygan, 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 $2,956.

From$315/night
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Beautiful 3BR Home Near Lake MI - Sheboygan, WI

Beautiful 3BR Home Near Lake MI

Holiday Home, Sheboygan

Beautiful 3BR Home Near Lake MI is a holiday home in Sheboygan, with parking and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Beautiful 3BR Home Near Lake MI

Beautiful 3BR Home Near Lake MI is a holiday home in Sheboygan, with parking and room for a group. 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 ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,017.

From$501/night
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The Rochester Inn, A Historic Hotel - Sheboygan, WI

The Rochester Inn, A Historic Hotel

B & B, Sheboygan

The Rochester Inn, A Historic Hotel is a b & b in Sheboygan, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About The Rochester Inn, A Historic Hotel

The Rochester Inn, A Historic Hotel is a b & b in Sheboygan, 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 breakfast, free wifi, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,916.

From$375/night
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Best Pet-Friendly Vacation Rentals in Sheboygan, WI

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

Logan Ave Holiday House - Upper - Sheboygan, WI

Logan Ave Holiday House - Upper

Apartment, Sheboygan

Logan Ave Holiday House - Upper is a apartment in Sheboygan, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Logan Ave Holiday House - Upper

Logan Ave Holiday House - Upper is a apartment in Sheboygan, 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 cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,219.

From$225/night
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Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan - Sheboygan, WI

Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan

Apartment, Sheboygan

Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan is a apartment in Sheboygan, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan

Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan is a apartment in Sheboygan, 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 cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,378.

From$242/night
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Cozy & Spacious 4BR Getaway Near Lake Michigan – AC & Outdoor Dining - Sheboygan, WI

Cozy & Spacious 4BR Getaway Near Lake Michigan – AC & Outdoor Dining

Holiday Home, Sheboygan

Cozy & Spacious 4BR Getaway Near Lake Michigan – AC & Outdoor Dining is a holiday home in Sheboygan, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers…

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About Cozy & Spacious 4BR Getaway Near Lake Michigan – AC & Outdoor Dining

Cozy & Spacious 4BR Getaway Near Lake Michigan – AC & Outdoor Dining is a holiday home in Sheboygan, with pet-friendly space, kitchen access, and room for a group. 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 $3,808.

From$432/night
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3 mins from Ryder - Sheboygan, WI

3 mins from Ryder

Apartment, Sheboygan

3 mins from Ryder is a apartment in Sheboygan, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About 3 mins from Ryder

3 mins from Ryder is a apartment in Sheboygan, with pet-friendly space, pool 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 cancellation, pool, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $24,073.

From$3,000/night
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Best Sheboygan, WI vacation rentals with a kitchen

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

Private, 4-bedroom, 2.5-bath near Kohler golf & walking distance to winery! - Sheboygan, WI

Private, 4-bedroom, 2.5-bath near Kohler golf & walking distance to winery!

Holiday Home, Sheboygan

Private, 4-bedroom, 2.5-bath near Kohler golf & walking distance to winery! is a holiday home in Sheboygan, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Private, 4-bedroom, 2.5-bath near Kohler golf & walking distance to winery!

Private, 4-bedroom, 2.5-bath near Kohler golf & walking distance to winery! is a holiday home in Sheboygan, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

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

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $14,871.

From$1,620/night
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Summer plans? Beat the crowds and get the dates you want! - Sheboygan, WI

Summer plans? Beat the crowds and get the dates you want!

Holiday Home, Sheboygan

Summer plans? Beat the crowds and get the dates you want! is a holiday home in Sheboygan, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Summer plans? Beat the crowds and get the dates you want!

Summer plans? Beat the crowds and get the dates you want! is a holiday home in Sheboygan, with 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, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $18,354.

From$2,134/night
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Secluded Sanctuary with Beach and Woods - Sheboygan, WI

Secluded Sanctuary with Beach and Woods

Holiday Home, Sheboygan

Secluded Sanctuary with Beach and Woods is a holiday home in Sheboygan, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Secluded Sanctuary with Beach and Woods

Secluded Sanctuary with Beach and Woods is a holiday home in Sheboygan, 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: hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $20,279.

From$2,446/night
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Serene Lakeview Retreat on Lake Michigan - Minutes to Whistling Straights - Sheboygan, WI

Serene Lakeview Retreat on Lake Michigan - Minutes to Whistling Straights

Holiday Home, Sheboygan

Serene Lakeview Retreat on Lake Michigan - Minutes to Whistling Straights is a holiday home in Sheboygan, with kitchen access and a quieter setting. This stay gives travelers a comfortable…

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About Serene Lakeview Retreat on Lake Michigan - Minutes to Whistling Straights

Serene Lakeview Retreat on Lake Michigan - Minutes to Whistling Straights is a holiday home in Sheboygan, with kitchen access and a quieter setting. 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 kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $65,383.

From$8,000/night
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Our Favorite Family-Friendly Vacation Rentals in Sheboygan, WI

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

Wonderful 3+ Bedroom Home Completely Renovated - Sheboygan, WI

Wonderful 3+ Bedroom Home Completely Renovated

Holiday Home, Sheboygan

Wonderful 3+ Bedroom Home Completely Renovated is a holiday home in Sheboygan, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring…

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About Wonderful 3+ Bedroom Home Completely Renovated

Wonderful 3+ Bedroom Home Completely Renovated is a holiday home in Sheboygan, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, kids friendly, kids friendly videos or books, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,477.

From$255/night
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Secluded Sanctuary with Beach and Woods - Sheboygan, WI

Secluded Sanctuary with Beach and Woods

Cottage, Sheboygan

Secluded Sanctuary with Beach and Woods is a cottage in Sheboygan, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Secluded Sanctuary with Beach and Woods

Secluded Sanctuary with Beach and Woods is a cottage in Sheboygan, 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, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,776.

From$312/night
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Beautiful 3BR Home Near Lake MI - Sheboygan, WI

Beautiful 3BR Home Near Lake MI

Holiday Home, Sheboygan

Beautiful 3BR Home Near Lake MI is a holiday home in Sheboygan, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Beautiful 3BR Home Near Lake MI

Beautiful 3BR Home Near Lake MI is a holiday home in Sheboygan, with kitchen access and room for a group. 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 kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,315.

From$345/night
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Cozy Corner Cottage - Dutch Colonial Step from Beach - Sheboygan, WI

Cozy Corner Cottage - Dutch Colonial Step from Beach

Holiday Home, Sheboygan

Cozy Corner Cottage - Dutch Colonial Step from Beach is a holiday home in Sheboygan, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Cozy Corner Cottage - Dutch Colonial Step from Beach

Cozy Corner Cottage - Dutch Colonial Step from Beach is a holiday home in Sheboygan, 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 cancellation, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,805.

From$398/night
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