Sheboygan holiday rentals

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Booking Insights
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Best Sheboygan vacation rentals

These are the best prices for 8-9 May.
Dog-Friendly Sheboygan Home - 1 Mi to Town! - Sheboygan - Living room
Dog-Friendly Sheboygan Home - 1 Mi to Town!
Sheboygan, WI, United States
9.9Wonderful(17)
House
R3 550+
Check availability
Pet-Friendly Sheboygan Home, 1 Mi to Lake Michigan - Sheboygan - Living room
Pet-Friendly Sheboygan Home, 1 Mi to Lake Michigan
Sheboygan, WI, United States
9.8Wonderful(13)
House
R6 935+
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Remodeled Home On Lake Michigan - Sheboygan - Living room
Remodeled Home On Lake Michigan
Sheboygan, WI, United States
9.7Wonderful(35)
House
R4 601+
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Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops! - Sheboygan - Bedroom
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
Sheboygan, WI, United States
9.8Wonderful(10)
Apartment
R4 043+
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Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan - Sheboygan - Living room
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Sheboygan, WI, United States
9.6Wonderful(20)
Apartment
R2 153+
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Luxe Manor With Modern, Elegant Vibes - Sheboygan - Living room
Luxe Manor With Modern, Elegant Vibes
Sheboygan, WI, United States
9.8Wonderful(10)
House
R8 644+
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Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home - Sheboygan - Building
Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home
Sheboygan, WI, United States
9.7Wonderful(86)
Condo
R6 130+
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Lake Michigan Home with gorgeous views, great spot for family or golf retreat - Sheboygan - Balcony
Lake Michigan Home with gorgeous views, great spot for family or golf retreat
Sheboygan, WI, United States
9.8Wonderful(61)
House
R18 208+
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Beach front luxury spacious villa ! - Sheboygan - Bedroom
Beach front luxury spacious villa !
Sheboygan, WI, United States
9.8Wonderful(44)
Villa
R7 461+
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Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host! - Sheboygan - Living room
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
Sheboygan, WI, United States
9.6Wonderful(95)
House
R4 848+
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Wandering Waves - Beachfront Lake Michigan Stay! - Sheboygan - Living room
Wandering Waves - Beachfront Lake Michigan Stay!
Sheboygan, WI, United States
9.8Wonderful(10)
Villa
R5 982+
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Seagull Beach Guest House, Unique Lake Michigan Cottage on private beach - Sheboygan - Living room
Seagull Beach Guest House, Unique Lake Michigan Cottage on private beach
Sheboygan, WI, United States
10Wonderful(98)
Cottage
R4 799+
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Updated Sheboygan Home w/ Porch 1 Mi to Beach - Sheboygan
Updated Sheboygan Home w/ Porch 1 Mi to Beach
Sheboygan, WI, United States
9.6Wonderful(23)
House
R5 834+
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Family Home, 1 Block to Lake Michigan Beach! - Sheboygan
Family Home, 1 Block to Lake Michigan Beach!
Sheboygan, WI, United States
9.7Wonderful(16)
House
R7 461+
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Sheboygan Getaway with Deck and On-Site Lake Access! - Sheboygan
Sheboygan Getaway with Deck and On-Site Lake Access!
Sheboygan, WI, United States
9.8Wonderful(5)
Apartment
R5 834+
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Pet-Friendly Sheboygan Home 4 Mi to Lake Michigan - Sheboygan
Pet-Friendly Sheboygan Home 4 Mi to Lake Michigan
Sheboygan, WI, United States
House
R7 461+
Check availability
Booking Insights

KAYAK’s insights for holiday rentals in Sheboygan

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Sheboygan with confidence.

Which month has the cheapest vacation rental rates in Sheboygan?

Vacation rentals are cheapest in Sheboygan in August, with average rates of R1 435. In comparison, November is the most expensive month, with prices at R11 466.

Find deals

KAYAK's top tips for finding Sheboygan holiday rental deals

  • Holiday rentals in Sheboygan are around 40% cheaper than hotels on average. Search here to compare prices for all accommodation types in Sheboygan.
  • The best holiday rental properties in Sheboygan are Seagull Beach Guest House, Unique Lake Michigan Cottage on private beach (10,0, 98 reviews), Beachside Condo w Stunning Lake Views (10,0, 24), and Lake Michigan Home with gorgeous views, great spot for family or golf retreat (9,8, 61), based on ratings and reviews from real travellers.

FAQs when booking a holiday home in Sheboygan

  • What types of holiday rentals are available in Sheboygan?

    There are loads of different property types that you can make your holiday home in Sheboygan. You’ll find apartments, cabins, condos, cottages, houses, campsites, homestays and villas.

  • Are there any pet-friendly holiday rentals in Sheboygan?

    There are a number of dog and pet-friendly Sheboygan holiday rentals, with around 22% allowing you to bring your pet along with you.

  • How much is a holiday rental in Sheboygan for tonight?

    In the last 72 hours, users have found Sheboygan holiday rentals for tonight for as low as R5 646. Search here for similar prices

  • How can I find holiday rentals near me in Sheboygan?

    Take a look at our holiday rentals map to find the best holiday rental homes near you.

Where to stay in Sheboygan?

Our map will help you find the perfect place to stay in Sheboygan by showing you the exact location of each holiday rental.

Everything you need to know for your stay in Sheboygan