Home Vacation Rentals By Owner In Sheboygan, WI

Showing 100 Of 122 Vacation Rentals
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Exceptional(11)

$355.41

/ Nightly
Condo

Indigo Waters - Steps to the sand! 2BR | Sleeps 7!

Sheboygan, Wisconsin, United States

Bed 2

Bed

Bath 2

Bath

Sleep 7

Sleeps
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Exceptional(36)

$439.25

/ Nightly
Condo

Perfect Paradise | 4BR Lakeview Condo w/ Jacuzzi

Sheboygan, Wisconsin, United States

Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(43)

$914.81

/ Nightly
Private Vacation Home

Luxury Home Historic location 4BR-3 FullBath- Walk 3 min beach, 10 to downtown

Sheboygan, Wisconsin, United States

Bed 4

Bed

Bath 3

Bath

Sleep 9

Sleeps
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Exceptional(23)

$301.91

/ Nightly
Private Vacation Home

4BR Home Near Kohler. Fall Getaway. Sleeps 7.

Sheboygan, Wisconsin, United States

Bed 4

Bed

Bath 2

Bath

Sleep 7

Sleeps
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Exceptional(10)

$199.77

/ Nightly
Apartment

Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan

Sheboygan, Wisconsin, United States

Bed 3

Bed

Bath 1

Bath

Sleep 5

Sleeps
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Exceptional(266)

$205.16

/ Nightly
Private Vacation Home

Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!

Sheboygan, Wisconsin, United States

Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(1)

$424.5

/ Nightly
Private Vacation Home

Large Backyard, Walk to Hospital: Sheboygan Abode!

Sheboygan, Wisconsin, United States

Bed 2

Bed

Bath 1

Bath

Sleep 7

Sleeps
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Exceptional(9)

$339.37

/ Nightly
Private Vacation Home

Beach House on the shores of Lake Michigan Near downtown Sheboygan

Sheboygan, Wisconsin, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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$999.86

/ Nightly
Private Vacation Home

Whistling Straights 4 min, Blackwolf Run 7 min, Erin Hills 84 min, 3 Bedroom

Sheboygan, Wisconsin, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(1)

$537.03

/ Nightly
Private Vacation Home

Beachside Beautifully Renovated Historic Home

Sheboygan, Wisconsin, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(26)

$381.48

/ Nightly
Private Vacation Home

Classic brick charmer close to lake, river, and downtown!

Sheboygan, Wisconsin, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(8)

$180.94

/ Nightly
Private Vacation Home

Peaceful Home Base: Comfy Beds: Road America, Golf & Lake Michigan

Howards Grove, Wisconsin, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(1)

$327.49

/ Nightly
Cottage

Lake Breeze Cottage. One block from the lake, walking distance to downtown!

Sheboygan, Wisconsin, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(1)

$711.65

/ Nightly
Private Vacation Home

Luxury Pool Retreat - 2 Acres - Near Whistling Straits

Sheboygan, Wisconsin, United States

Bed 4

Bed

Bath 4

Bath

Sleep 12

Sleeps
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Exceptional(33)

$277.99

/ Nightly
Condo

Beachside Condo Downtown with Lake Michigan Views

Sheboygan, Wisconsin, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(43)

$254.23

/ Nightly
Condo

Beachside Condo w/ Stunning Lake Views

Sheboygan, Wisconsin, United States

Bed 2

Bed

Bath 1

Bath

Sleep 5

Sleeps
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Exceptional(28)

$192.96

/ Nightly
Private Vacation Home

Dog-Friendly Sheboygan Home - 1 Mi to Town!

Sheboygan, Wisconsin, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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Exceptional(14)

$616.31

/ Nightly
Private Vacation Home

The Links! - Luxury Golf Retreat with Golf Simulator

Sheboygan, Wisconsin, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(11)

$1003.84

/ Nightly
Private Vacation Home

Lakeview Farm | Beach · Hot Tub · Theater · Views

Sheboygan, Wisconsin, United States

Bed 6

Bed

Bath 5

Bath

Sleep 14

Sleeps
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Exceptional(17)

$473.17

/ Nightly
Private Vacation Home

Spacious Sheboygan Home w/ Grill & Fire Pit!

Sheboygan, Wisconsin, United States

Bed 5

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Home Most popular vacation rentals in Sheboygan

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Exceptional(17)

$327.49

/ Nightly
Cottage

Lake Breeze Cottage. One block from the lake, walking distance to downtown!

Sheboygan, Wisconsin, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(17)

$277.99

/ Nightly
Condo

Beachside Condo Downtown with Lake Michigan Views

Sheboygan, Wisconsin, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(17)

$289.43

/ Nightly
Private vacation home

REMODELED HOME ON LAKE MICHIGAN

Sheboygan, Wisconsin, United States

Bed 3

Bed

Bath 1

Bath

Sleep 7

Sleeps
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Exceptional(17)

$301.91

/ Nightly
Private vacation home

4BR Home Near Kohler. Fall Getaway. Sleeps 7.

Sheboygan, Wisconsin, United States

Bed 4

Bed

Bath 2

Bath

Sleep 7

Sleeps
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Exceptional(17)

$302.48

/ Nightly
Condo

The Cottage | Beachfront Condo on Lake Michigan

Sheboygan, Wisconsin, United States

Bed 2

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(17)

$308.72

/ Nightly
Private vacation home

2 bed/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub

Sheboygan, Wisconsin, United States

Bed 2

Bed

Bath 2

Bath

Sleep 5

Sleeps
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Exceptional(17)

$312.98

/ Nightly
Condo

Malibu of the Midwest Condo steps from the Lake

Sheboygan, Wisconsin, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(17)

$321.43

/ Nightly
Private vacation home

Steps from Lake Michigan: North Point Place

Sheboygan, Wisconsin, United States

Bed 3

Bed

Bath 1

Bath

Sleep 7

Sleeps
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Exceptional(17)

$354.69

/ Nightly
Private vacation home

Cozy Corner Cottage| Beach Access & Historic Charm

Sheboygan, Wisconsin, United States

Bed 3

Bed

Bath 1

Bath

Sleep 7

Sleeps
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Exceptional(17)

$349.02

/ Nightly
Villa

Wandering Waves | Beachfront Lake Michigan Stay!

Sheboygan, Wisconsin, United States

Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps

Most Popular Cities in Wisconsin