Photo by John Sukowaty
Sheboygan Holiday Rentals
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Our top choices for Sheboygan holiday rentals

Aparthotel in Elkhart Lake
Victorian Inn Elkhart Lake Wisconsin8.8 out of 10, Excellent, (3)

Aparthotel in Downtown Sheboygan
Grandstay Residential Suites Hotel - Sheboygan8.6 out of 10, Excellent, (1015)
The price is HK$971
HK$1,102 total
includes taxes & fees
1 Jan - 2 Jan 2026

Cottage in Sheboygan
Large Backyard, Walk to Hospital: Sheboygan Abode!The price is HK$1,143
HK$3,130 total
includes taxes & fees
3 Jan - 4 Jan 2026

Villa in Elkhart Lake
First Floor Pet Friendly Queen Suite with Single Pull-out10.0 out of 10, Exceptional, (2)

Holiday Home in Oostburg
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.10.0 out of 10, Exceptional, (116)
The price is HK$933
HK$1,148 total
includes taxes & fees
12 Jan - 13 Jan 2026

Apartment in Ellis Historical District
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan9.8 out of 10, Exceptional, (24)
The price is HK$739
HK$1,015 total
includes taxes & fees
4 Jan - 5 Jan 2026

Apartment in Sheboygan
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI10.0 out of 10, Exceptional, (4)
The price is HK$700
HK$1,324 total
includes taxes & fees
11 Jan - 12 Jan 2026

Apartment in Sheboygan
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan9.2 out of 10, Wonderful, (10)
The price is HK$630
HK$1,245 total
includes taxes & fees
4 Jan - 5 Jan 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Sheboygan Hotel Reviews

Comfort Inn & Suites Sheboygan I-43
10/10 Excellent
Find out more about Sheboygan
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