Vacation rentals in Sheboygan County, WI

34 available vacation rental offers

airbnbBooking.comVrboExpediaSonderpricelineTripadvisorTrip.comHomestayHotels.comOrbitz

Choose the perfect vacation accommodation

Price per night

Up to $100$100 - 200From $200

Accommodation type

Vacation rentals

Rating

Excellent 9+Very good 8+Good 7+All ratings

Best Vacation rentals and Airbnb offers in Sheboygan County, WI

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

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

Homestay, Sheboygan County

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

Read more

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 County, 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
Show
2 Mi to Dtwn: Studio Suite in Sheboygan - Sheboygan County, WI

2 Mi to Dtwn: Studio Suite in Sheboygan

Apartment, Sheboygan County

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

Read more

About 2 Mi to Dtwn: Studio Suite in Sheboygan

2 Mi to Dtwn: Studio Suite in Sheboygan is a apartment in Sheboygan County, 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
Show
2 Mi to Dtwn: Studio Suite in Sheboygan - Sheboygan County, WI

2 Mi to Dtwn: Studio Suite in Sheboygan

Apartment, Sheboygan County

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

Read more

About 2 Mi to Dtwn: Studio Suite in Sheboygan

2 Mi to Dtwn: Studio Suite in Sheboygan is a apartment in Sheboygan County, 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 $906.

From$129/night
Show
Dtwn Sheboygan Apt Above Local Bar! - Sheboygan County, WI

Dtwn Sheboygan Apt Above Local Bar!

Apartment, Sheboygan County

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

Read more

About Dtwn Sheboygan Apt Above Local Bar!

Dtwn Sheboygan Apt Above Local Bar! is a apartment in Sheboygan County, 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, free wifi, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,528.

From$132/night
Show

Browse Vacation Rentals with a Pool in Sheboygan County, WI

Add a pool to the search when you want an easy place to cool off between outings.

Experience Lake Michigan views from your cozy 3-bedroom retreat - Sheboygan County, WI

Experience Lake Michigan views from your cozy 3-bedroom retreat

Holiday Home, Sheboygan County

Experience Lake Michigan views from your cozy 3-bedroom retreat is a holiday home in Sheboygan County, with pool access, room for a group, and a quieter setting. This stay gives travelers a…

Read more

About Experience Lake Michigan views from your cozy 3-bedroom retreat

Experience Lake Michigan views from your cozy 3-bedroom retreat is a holiday home in Sheboygan County, with pool access, room for a group, 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: pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,878.

From$554/night
Show
Waterfront and Pool View Condo!! - Sheboygan County, WI

Waterfront and Pool View Condo!!

Villa, Sheboygan County

Waterfront and Pool View Condo!! is a villa in Sheboygan County, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the…

Read more

About Waterfront and Pool View Condo!!

Waterfront and Pool View Condo!! is a villa in Sheboygan County, with pool access, 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: pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,919.

From$846/night
Show
A Short Walk to The Beach! - Sheboygan County, WI

A Short Walk to The Beach!

Condo, Sheboygan County

A Short Walk to The Beach! is a condo in Sheboygan County, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

Read more

About A Short Walk to The Beach!

A Short Walk to The Beach! is a condo in Sheboygan County, with pool access 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: free cancellation, pool, ac, air conditioning, and internet.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $8,139.

From$1,163/night
Show
Experience Gracious Living & Destination Kohler - Sheboygan County, WI

Experience Gracious Living & Destination Kohler

Holiday Home, Sheboygan County

Experience Gracious Living & Destination Kohler is a holiday home in Sheboygan County, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Experience Gracious Living & Destination Kohler

Experience Gracious Living & Destination Kohler is a holiday home in Sheboygan County, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $11,183.

From$1,598/night
Show

Best Sheboygan County, 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 County, WI

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

Holiday Home, Sheboygan County

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

Read more

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 County, 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 $2,095.

From$299/night
Show
Beautiful 3BR Home Near Lake MI - Sheboygan County, WI

Beautiful 3BR Home Near Lake MI

Holiday Home, Sheboygan County

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

Read more

About Beautiful 3BR Home Near Lake MI

Beautiful 3BR Home Near Lake MI is a holiday home in Sheboygan County, 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
Show
Private, 4-bedroom, 2.5-bath near Kohler golf & walking distance to winery! - Sheboygan County, WI

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

Holiday Home, Sheboygan County

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

Read more

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 County, 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 $13,102.

From$1,872/night
Show

Best Pet-Friendly Vacation Rentals in Sheboygan County, WI

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

Rustic Cozy A frame! Hike, Fish, Kayak, Relax! June 1-10 available! - Sheboygan County, WI

Rustic Cozy A frame! Hike, Fish, Kayak, Relax! June 1-10 available!

Cabin, Sheboygan County

Rustic Cozy A frame! Hike, Fish, Kayak, Relax! June 1-10 available! is a cabin in Sheboygan County, with pet-friendly space, parking, and kitchen access. This stay gives travelers a…

Read more

About Rustic Cozy A frame! Hike, Fish, Kayak, Relax! June 1-10 available!

Rustic Cozy A frame! Hike, Fish, Kayak, Relax! June 1-10 available! is a cabin in Sheboygan County, 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 $1,487.

From$212/night
Show
Logan Ave Holiday House - Upper - Sheboygan County, WI

Logan Ave Holiday House - Upper

Apartment, Sheboygan County

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

Read more

About Logan Ave Holiday House - Upper

Logan Ave Holiday House - Upper is a apartment in Sheboygan County, 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 $1,955.

From$279/night
Show
Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan - Sheboygan County, WI

Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan

Apartment, Sheboygan County

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

Read more

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

Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan is a apartment in Sheboygan County, 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 $2,095.

From$299/night
Show
Beautifully Updated Two Queen Suite - Sheboygan County, WI

Beautifully Updated Two Queen Suite

Villa, Sheboygan County

Beautifully Updated Two Queen Suite is a villa in Sheboygan County, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for exploring the…

Read more

About Beautifully Updated Two Queen Suite

Beautifully Updated Two Queen Suite is a villa in Sheboygan County, 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: pool, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,557.

From$508/night
Show

Best Sheboygan County, WI vacation rentals with a kitchen

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

GGG Log Cabin Apartment on the Ice Age Trail - Sheboygan County, WI

GGG Log Cabin Apartment on the Ice Age Trail

Apartment, Sheboygan County

GGG Log Cabin Apartment on the Ice Age Trail is a apartment in Sheboygan County, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

Read more

About GGG Log Cabin Apartment on the Ice Age Trail

GGG Log Cabin Apartment on the Ice Age Trail is a apartment in Sheboygan County, 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 $1,191.

From$170/night
Show
Beautiful 3BR Home Near Lake MI - Sheboygan County, WI

Beautiful 3BR Home Near Lake MI

Holiday Home, Sheboygan County

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

Read more

About Beautiful 3BR Home Near Lake MI

Beautiful 3BR Home Near Lake MI is a holiday home in Sheboygan County, 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 $2,924.

From$418/night
Show
Beautiful private home hidden in the woods. Can sleep 11 guests - Sheboygan County, WI

Beautiful private home hidden in the woods. Can sleep 11 guests

Holiday Home, Sheboygan County

Beautiful private home hidden in the woods. Can sleep 11 guests is a holiday home in Sheboygan County, with kitchen access. This stay gives travelers a comfortable base for exploring the…

Read more

About Beautiful private home hidden in the woods. Can sleep 11 guests

Beautiful private home hidden in the woods. Can sleep 11 guests is a holiday home in Sheboygan County, 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 $5,729.

From$818/night
Show
Secluded Sanctuary with Beach and Woods - Sheboygan County, WI

Secluded Sanctuary with Beach and Woods

Holiday Home, Sheboygan County

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

Read more

About Secluded Sanctuary with Beach and Woods

Secluded Sanctuary with Beach and Woods is a holiday home in Sheboygan County, 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 $19,436.

From$2,777/night
Show

Our Favorite Family-Friendly Vacation Rentals in Sheboygan County, WI

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

Charming 2-bedroom cottage on Long Lake Dundee. WI Property right on the water - Sheboygan County, WI

Charming 2-bedroom cottage on Long Lake Dundee. WI Property right on the water

Cottage, Sheboygan County

Charming 2-bedroom cottage on Long Lake Dundee. WI Property right on the water is a cottage in Sheboygan County, with room for a group. This stay gives travelers a comfortable base for…

Read more

About Charming 2-bedroom cottage on Long Lake Dundee. WI Property right on the water

Charming 2-bedroom cottage on Long Lake Dundee. WI Property right on the water is a cottage in Sheboygan County, with 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, ac, air conditioning, heating, and living room.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,356.

From$194/night
Show
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops! - Sheboygan County, WI

Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!

Apartment, Sheboygan County

Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops! is a apartment in Sheboygan County, with pet-friendly space and kitchen access. This stay gives travelers a…

Read more

About Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!

Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops! is a apartment in Sheboygan County, 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 $1,747.

From$250/night
Show
Wonderful 3+ Bedroom Home Completely Renovated - Sheboygan County, WI

Wonderful 3+ Bedroom Home Completely Renovated

Holiday Home, Sheboygan County

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

Read more

About Wonderful 3+ Bedroom Home Completely Renovated

Wonderful 3+ Bedroom Home Completely Renovated is a holiday home in Sheboygan County, 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 $2,182.

From$312/night
Show
Secluded Sanctuary with Beach and Woods - Sheboygan County, WI

Secluded Sanctuary with Beach and Woods

Cottage, Sheboygan County

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

Read more

About Secluded Sanctuary with Beach and Woods

Secluded Sanctuary with Beach and Woods is a cottage in Sheboygan County, 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 $2,654.

From$379/night
Show