Photo by John Sukowaty
Holiday Homes in Sheboygan
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Our top choices for Sheboygan holiday homes

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 NZ$253
includes taxes & fees
5 Jan - 6 Jan 2026

Holiday Home in Fond du Lac
Best House in Wisconsin! Live like a STAR! VRBO Luxury! Huge Bar & Movie Theater10.0 out of 10, Exceptional, (1)
The price is NZ$5,597
includes taxes & fees
5 Jan - 6 Jan 2026

Holiday Home in Two Rivers
Hot Tub, Fire Pit, Point Beach & Neshotah BeachThe price is NZ$771
includes taxes & fees
3 Jan - 4 Jan 2026

Holiday Home in Ellis Historical District
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.9.6 out of 10, Exceptional, (12)
The price is NZ$263
includes taxes & fees
6 Jan - 7 Jan 2026

Holiday Home in Sheboygan
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!9.8 out of 10, Exceptional, (255)
The price is NZ$537
includes taxes & fees
31 Dec - 1 Jan 2026

Holiday Home in Sheboygan
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit10.0 out of 10, Exceptional, (6)
The price is NZ$303
includes taxes & fees
13 Jan - 14 Jan 2026

Holiday Home in Sheboygan
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city10.0 out of 10, Exceptional, (21)
The price is NZ$684
includes taxes & fees
3 Jan - 4 Jan 2026

Holiday Home in New Holstein
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!10.0 out of 10, Exceptional, (173)
The price is NZ$574
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.
Top Sheboygan Hotel Reviews

Watershed Hotel
10/10 Excellent
Find out more about Sheboygan
Sheboygan Holiday Homes information
Number of reviews | 807 |
|---|---|
Accommodation | 262 Holiday Homes |
Lowest Price | NZ$253 |
Highest Price | NZ$5,597 |
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