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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)
"We loved the cozy cottage and cuddled up with books under the afghans on the cool evenings. The lake was a pleasant walk away."
bev w.
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)
"Our large family had a magical Christmas! Our beautifully decorated rented home had everything we needed . We were all very comfortable during the day and night time sleeping . We had private spaces and family get together areas ."
Brenda J.
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)
"A warm and cozy place to stay. Beautifully decorated and friendly hosts. Would stay again anytime we’re in Sheboygan."
Rebecca S.
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)
"Beautiful view and perfect for our Wisconsin lake getaway."
Holly A.
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)
"4 forever friends getaway. Relaxation, eats and drinks with a little antique and thrift shopping"
Stacy P.
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)
"Wonderfully close to the lake. Sad there was no off street parking."
Lucas T.
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)
"Great place would go back"
William
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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