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Sheboygan holiday rentals

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Booking Insights
Recommended by KAYAK

Best Sheboygan vacation rentals

These are the best prices for 3-4 Oct.
Dog-Friendly Sheboygan Home - 1 Mi to Town! - Sheboygan - Living room
Dog-Friendly Sheboygan Home - 1 Mi to Town!
Sheboygan, WI, United States
10Wonderful(22)
House
R3 017+
Check availability
Updated Sheboygan Home w/ Porch 1 Mi to Beach - Sheboygan - Balcony
Updated Sheboygan Home w/ Porch 1 Mi to Beach
Sheboygan, WI, United States
9.6Wonderful(24)
House
R6 100+
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Remodeled Home On Lake Michigan - Sheboygan - Living room
Remodeled Home On Lake Michigan
Sheboygan, WI, United States
9.7Wonderful(41)
House
R4 989+
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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
R11 040+
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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(16)
Apartment
R5 593+
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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
9.5Wonderful(24)
Apartment
R2 171+
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Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan - Sheboygan - Living room
Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan
Sheboygan, WI, United States
9.6Wonderful(12)
Apartment
R5 844+
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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(93)
Condo
R5 967+
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Eclectic Spacious 3 Br Home Near Lake MI W/ Fire Pit - Sheboygan - Bedroom
Eclectic Spacious 3 Br Home Near Lake MI W/ Fire Pit
Sheboygan, WI, United States
9.8Wonderful(15)
House
R4 275+
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Lake Breeze on 11th - Sheboygan - Living room
Lake Breeze on 11th
Sheboygan, WI, United States
9.5Wonderful(14)
House
R3 183+
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Scenic Lake Views in Sheboygan - Sheboygan - Living room
Scenic Lake Views in Sheboygan
Sheboygan, WI, United States
9.5Wonderful(36)
Condo
R5 188+
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Overlook Oasis | Coastal Haven in Ellis District - Sheboygan - Bedroom
Overlook Oasis | Coastal Haven in Ellis District
Sheboygan, WI, United States
10Wonderful(6)
Apartment
R4 308+
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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(63)
House
R12 250+
Check availability
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(97)
House
R4 359+
Check availability
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(107)
Cottage
R3 763+
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Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city - Sheboygan - Bedroom
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
Sheboygan, WI, United States
9.8Wonderful(20)
House
R9 481+
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.

What is the cheapest day of the week to book a vacation rental in Sheboygan?

Tuesday offers the lowest rates in Sheboygan, with an average nightly price of R2 164. The highest prices are found on Friday, with average rates at R12 591.

How much is a vacation rental in Sheboygan for this weekend by property type?

The best deal for a vacation rental in Sheboygan found by KAYAK users for the upcoming weekend was R3 970 in a Holiday park. Apartments prices start at R9 455 and Houses at R15 578.

Find deals

KAYAK's top tips for finding Sheboygan holiday rental deals

  • Pool is the most popular holiday rental property amenity in Sheboygan
  • Holiday rentals in Sheboygan are around 4% more expensive than hotels on average. Search here to compare prices for all accommodation types in Sheboygan.
  • The best holiday rental properties in Sheboygan are Dog-Friendly Sheboygan Home - 1 Mi to Town! (10,0, 22 reviews), Seagull Beach Guest House, Unique Lake Michigan Cottage on private beach (10,0, 107), and Beachside Condo w Stunning Lake Views (10,0, 30), 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 24% 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 R20 187. Search here for similar prices

  • How much is a holiday rental in Sheboygan for this weekend?

    In the last 72 hours, users have found Sheboygan holiday rentals for this weekend for as low as R7 422 per night. 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.

More options for your stay in Sheboygan

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Car hire in Sheboygan