Sheboygan holiday rentals

KAYAK searches hundreds of travel sites at once for holiday home deals in Sheboygan

Here is why travellers choose KAYAK

Free to useThere are no hidden charges or fees

Filter your dealsFilter by free cancellation, free breakfast and more.

Millions of reviewsCheck ratings based on millions of real guest reviews.

Recommended by KAYAK
Booking Insights
Recommended by KAYAK

Best Sheboygan vacation rentals

Go to map

Search by review score

6+ Okay7+ Good8+ Great9+ Excellent

Search by price

R1 081 - R9 644R9 644 - R18 189R18 189 - R26 734R26 734 - R35 279R35 279+ per night

Property Types

ApartmentCondoCottageHomestayHouse

Search by freebies

Free cancellationFree breakfastFree parkingFree internet

Most recommended vacation rentals in Sheboygan

Show all
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 598+
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(9)
Free Wi-Fi
Pet-friendly
Air conditioning
R2 947+
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)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R2 564+
Check availability
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
R3 523+
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)
Free Wi-Fi
Air conditioning
R1 343+
Check availability
A Glorious Getaway Sheboygan - Blue Harbor Condo - Sheboygan - Balcony
A Glorious Getaway Sheboygan - Blue Harbor Condo
Sheboygan, WI, United States
9.7Wonderful(17)
Parking
Free Wi-Fi
Air conditioning
R10 655+
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(50)
Free Wi-Fi
Air conditioning
R3 662+
Check availability
Scenic Lake Views in Sheboygan - Sheboygan - Living room
Scenic Lake Views in Sheboygan
Sheboygan, WI, United States
9.4Wonderful(27)
Free Wi-Fi
Air conditioning
R5 284+
Check availability
Beachside Getaway In Sheboygan - Sheboygan - Living room
Beachside Getaway In Sheboygan
Sheboygan, WI, United States
10Wonderful(21)
Free Wi-Fi
Air conditioning
R4 220+
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
R4 639+
Check availability
Modern South Pier Condo on Sheboygan River! - Sheboygan - Balcony
Modern South Pier Condo on Sheboygan River!
Sheboygan, WI, United States
10Wonderful(3)
Free Wi-Fi
Air conditioning
R5 528+
Check availability
Amazing Villa Rental Near Lake Michigan - Sheboygan - Patio
Amazing Villa Rental Near Lake Michigan
Sheboygan, WI, United States
10Wonderful(12)
Free Wi-Fi
Air conditioning
R36 796+
Check availability
2 Mi to Dtwn Studio Suite in Sheboygan - Sheboygan
2 Mi to Dtwn Studio Suite in Sheboygan
Sheboygan, WI, United States
10Wonderful(1)
Free Wi-Fi
Pet-friendly
Air conditioning
R2 651+
Check availability
Sandhill - Sheboygan
Sandhill
Sheboygan, WI, United States
Air conditioning
R21 014+
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)
Parking
Free Wi-Fi
Air conditioning
R1 779+
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 191+
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 620. The highest prices are found on Saturday, with average rates at R11 862.
Find deals

KAYAK's top tips for finding Sheboygan holiday rental deals

  • Holiday rentals in Sheboygan are around 80% 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, 50), and Beachside Getaway In Sheboygan (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 7% allowing you to bring your pet along with you.

  • 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

Not what you’re looking for? Find thousands of other hotels, flights and car hire with KAYAK.