Sheboygan holiday rentals

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Best Sheboygan vacation rentals

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R1 232 - R14 194R14 194 - R27 139R27 139 - R40 084R40 084 - R53 029R53 029+ per night

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Most recommended vacation rentals in Sheboygan

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Dtwn Sheboygan Apt Above Local Bar! - Sheboygan - Living room
Dtwn Sheboygan Apt Above Local Bar!
Sheboygan, WI, United States
7.8Good(4)
Free Wi-Fi
Pet-friendly
Air conditioning
R4 980+
Check availability
Plymouth Rock Camping Resort - Sheboygan - Patio
Plymouth Rock Camping Resort
Sheboygan, WI, United States
8.8Very Good(6)
Parking
Free Wi-Fi
Pool
Air conditioning
R2 586+
Check availability
Dog-Friendly Sheboygan Home - 1 Mi to Town! - Sheboygan - Living room
Dog-Friendly Sheboygan Home - 1 Mi to Town!
Sheboygan, WI, United States
10Wonderful(4)
Free Wi-Fi
Pet-friendly
Air conditioning
R3 280+
Check availability
Family-Friendly House Walk to Lake Michigan! - Sheboygan - Kitchen
Family-Friendly House Walk to Lake Michigan!
Sheboygan, WI, United States
9.6Wonderful(9)
Free Wi-Fi
Pet-friendly
Air conditioning
R4 876+
Check availability
Private, 4-bedroom, 2.5-bath near Kohler golf & walking distance to winery! - Sheboygan - Kitchen
Private, 4-bedroom, 2.5-bath near Kohler golf & walking distance to winery!
Sheboygan, WI, United States
Air conditioning
R39 807+
Check availability
Ontario Ave - Kiwanis Park - Sheboygan - Outdoor view
Ontario Ave - Kiwanis Park
Sheboygan, WI, United States
10Wonderful(1)
Free Wi-Fi
Pet-friendly
Air conditioning
R1 336+
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A Glorious Getaway Sheboygan - Blue Harbor Condo - Sheboygan - Balcony
A Glorious Getaway Sheboygan - Blue Harbor Condo
Sheboygan, WI, United States
9.7Wonderful(15)
Parking
Free Wi-Fi
Air conditioning
R11 834+
Check availability
The River Bed - Condo sleeps 4 on west side - Sheboygan - Living room
The River Bed - Condo sleeps 4 on west side
Sheboygan, WI, United States
10Wonderful(49)
Free Wi-Fi
Air conditioning
R3 505+
Check availability
Beachside Getaway In Sheboygan - Sheboygan - Living room
Beachside Getaway In Sheboygan
Sheboygan, WI, United States
10Wonderful(20)
Free Wi-Fi
Air conditioning
R5 466+
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Riverfront Sheboygan Townhome with Grill! - Sheboygan - Living room
Riverfront Sheboygan Townhome with Grill!
Sheboygan, WI, United States
9.7Wonderful(14)
Free Wi-Fi
Air conditioning
R4 217+
Check availability
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(8)
Air conditioning
R5 223+
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2 Mi to Dtwn Studio Suite in Sheboygan - Sheboygan
2 Mi to Dtwn Studio Suite in Sheboygan
Sheboygan, WI, United States
Free Wi-Fi
Pet-friendly
Air conditioning
R2 603+
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)
Free Wi-Fi
Air conditioning
R6 143+
Check availability
Sandhill - Sheboygan
Sandhill
Sheboygan, WI, United States
Air conditioning
R20 910+
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Spacious & Peaceful Home in the heart of Sheboygan - Sheboygan
Spacious & Peaceful Home in the heart of Sheboygan
Sheboygan, WI, United States
8.0Very Good(8)
Parking
Free Wi-Fi
Air conditioning
R7 496+
Check availability
Private Guest Bedroom-1W West Room - Close to Lake Michigan - Sheboygan
Private Guest Bedroom-1W West Room - Close to Lake Michigan
Sheboygan, WI, United States
9.5Wonderful(2)
Parking
Free Wi-Fi
Air conditioning
R1 232+
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 R45 284. The highest prices are found on Monday, with average rates at R183 447.
Find deals

KAYAK's top tips for finding Sheboygan holiday rental deals

  • Holiday rentals in Sheboygan are around 64% 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 Seagull Beach Guest House, Unique Lake Michigan Cottage on private beach (10,0, 90 reviews), The River Bed - Condo sleeps 4 on west side (10,0, 49), and Beachside Getaway In Sheboygan (10,0, 20), 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, 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 16% 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 R3 648. 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 R2 610 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.

Everything you need to know for your stay in Sheboygan

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