Sheboygan holiday rentals

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Best Sheboygan vacation rentals

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R1 217 - R9 705R9 705 - R18 175R18 175 - R26 662R26 662 - R35 133R35 133+ per night

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Most recommended vacation rentals in Sheboygan

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Plymouth Rock Camping Resort - Sheboygan - Balcony
Plymouth Rock Camping Resort
Sheboygan, WI, United States
8.8Very Good(6)
Campsite
Parking
Free Wi-Fi
Pool
Air conditioning
R2 555+
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(12)
House
Free Wi-Fi
Pet-friendly
Air conditioning
R2 898+
Check availability
Spacious Home Near Lake MI w Fire Pit - Sheboygan - Bedroom
Spacious Home Near Lake MI w Fire Pit
Sheboygan, WI, United States
9.8Wonderful(9)
House
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R3 755+
Check availability
Dtwn Sheboygan Apt Above Local Bar! - Sheboygan - Kitchen
Dtwn Sheboygan Apt Above Local Bar!
Sheboygan, WI, United States
7.8Good(4)
Apartment
Free Wi-Fi
Pet-friendly
Air conditioning
R3 464+
Check availability
2BR Spacious Upper, Overlooking Kiwanis Park, Close to Everything! - Sheboygan - Bedroom
2BR Spacious Upper, Overlooking Kiwanis Park, Close to Everything!
Sheboygan, WI, United States
10Wonderful(1)
House
Free Wi-Fi
Air conditioning
R1 320+
Check availability
A Glorious Getaway Sheboygan - Blue Harbor Condo - Sheboygan - Balcony
A Glorious Getaway Sheboygan - Blue Harbor Condo
Sheboygan, WI, United States
9.7Wonderful(19)
Condo
Parking
Free Wi-Fi
Air conditioning
R12 414+
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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(52)
Condo
Free Wi-Fi
Air conditioning
R3 446+
Check availability
Scenic Lake Views in Sheboygan - Sheboygan - Living room
Scenic Lake Views in Sheboygan
Sheboygan, WI, United States
9.4Wonderful(31)
Condo
Free Wi-Fi
Air conditioning
R5 178+
Check availability
Beachside Getaway In Sheboygan - Sheboygan - Living room
Beachside Getaway In Sheboygan
Sheboygan, WI, United States
10Wonderful(22)
Condo
Free Wi-Fi
Air conditioning
R3 464+
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)
Apartment
Air conditioning
R5 092+
Check availability
Modern South Pier Condo on Sheboygan River! - Sheboygan - Balcony
Modern South Pier Condo on Sheboygan River!
Sheboygan, WI, United States
10Wonderful(3)
Apartment
Free Wi-Fi
Air conditioning
R5 607+
Check availability
Amazing Villa Rental Near Lake Michigan - Sheboygan - Patio
Amazing Villa Rental Near Lake Michigan
Sheboygan, WI, United States
10Wonderful(13)
House
Free Wi-Fi
Air conditioning
R37 207+
Check availability
2 Mi to Dtwn Studio Suite in Sheboygan - Sheboygan
2 Mi to Dtwn Studio Suite in Sheboygan
Sheboygan, WI, United States
8.5Very Good(2)
Apartment
Free Wi-Fi
Pet-friendly
Air conditioning
R2 606+
Check availability
Sandhill - Sheboygan
Sandhill
Sheboygan, WI, United States
Cabin
Air conditioning
R20 661+
Check availability
Private Guest Bedroom - 2E East Room - Close to Lake Michigan - Sheboygan
Private Guest Bedroom - 2E East Room - Close to Lake Michigan
Sheboygan, WI, United States
9.8Wonderful(12)
Homestay
Parking
Free Wi-Fi
Air conditioning
R1 680+
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
Free Wi-Fi
Air conditioning
R6 087+
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 576. The highest prices are found on Wednesday, with average rates at R13 250.
Find deals

KAYAK's top tips for finding Sheboygan holiday rental deals

  • Holiday rentals in Sheboygan are around 82% 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, 52), and Beachside Getaway In Sheboygan (10,0, 22), 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 8% 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 R10 677. 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