Sheboygan holiday rentals

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Booking Insights
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Best Sheboygan vacation rentals

These are the best prices for 28-29 Mar.
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(16)
House
R2 880+
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
R7 191+
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Dtwn Sheboygan Apt Above Local Bar! - Sheboygan - Kitchen
Dtwn Sheboygan Apt Above Local Bar!
Sheboygan, WI, United States
7.8Good(4)
Apartment
R5 180+
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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 533+
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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
9.7Wonderful(9)
Apartment
R4 567+
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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 896+
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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 232+
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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(85)
Condo
R5 504+
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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(94)
House
R4 499+
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Spacious Home Near Lake MI w Fire Pit - Sheboygan - Bedroom
Spacious Home Near Lake MI w Fire Pit
Sheboygan, WI, United States
9.8Wonderful(14)
House
R3 953+
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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(3)
Apartment
R3 902+
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Lake Breeze on 11th - Sheboygan - Living room
Lake Breeze on 11th
Sheboygan, WI, United States
9.4Wonderful(11)
House
R3 084+
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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 896+
Check availability
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
R6 049+
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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
R8 486+
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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
R4 857+
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 April, with average rates of R1 139. In comparison, March is the most expensive month, with prices at R12 662.

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

Sunday offers the lowest rates in Sheboygan, with an average nightly price of R1 100. The highest prices are found on Thursday, with average rates at R16 793.

Find deals

KAYAK's top tips for finding Sheboygan holiday rental deals

  • Holiday rentals in Sheboygan are around 71% 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 Beachside Condo w Stunning Lake Views (10,0, 23 reviews), Seagull Beach Guest House, Unique Lake Michigan Cottage on private beach (10,0, 97), and Beachside Condo Downtown with Lake Michigan Views (10,0, 21), 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 5% 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 323. 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