803+ Rental Villas and Private Getaways in Sheboygan |
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Sheboygan Vacation Rentals & Execstays Homes

About Sheboygan Vacation Rentals

There are more than 803 vacation rentals that are available in Sheboygan. These rentals, including vacation rentals, Execstays Homes (Execstays) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an Execstays property in Sheboygan.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Execstays Sheboygan, you have the flexibility of comparing different options of various deals with a single click. Looking for an Execstays with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by Execstays, and other popular Airbnb-style properties in Sheboygan. Places to stay near Sheboygan are 869.22 ftยฒ on average, with prices averaging $444 a night.

Execstays makes it easy and safe to find and compare vacation rentals in Sheboygan with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

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Top Rental Accommodation Types in Sheboygan

Type Count
Vacation Homes 411
Holiday Apartments 146
Villas 29
Cottages 22

Use these Quick Filters to Find a Vacation Rental in Sheboygan

โ˜… Pro Tip: Execstays makes it easy to compare the best listings on Execstays homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Execstays homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Sheboygan.

Weather in Sheboygan, WI

View the weather forecast for Sheboygan before booking your Sheboygan Vacation Rentals to confirm your best time to go.

December - February
High 60ยฐF       Low 26ยฐF
March - May
High 77ยฐF       Low 40ยฐF
June - August
High 91ยฐF       Low 64ยฐF
September - November
High 84ยฐF       Low 38ยฐF

Top Attractions Around Sheboygan, WI

ExecStays offers a large selection of top attractions around Sheboygan. Research things to do on your vacation before you visit Sheboygan.


Whistling Straits Golf Course
Blue Harbor Resort & Conference Center Water Park
Road America
Kettle Moraine State Forest
Wisconsin Maritime Museum
Kohler Design Center
Lincoln Park Zoo
Blackwolf Run
Skip Barber Driving School
Kohler-Andrae State Park
John Michael Kohler Arts Center
University of Wisconsin-Sheboygan
Chilton Speedway
St. Peter Claver Parish
Children's Museum
Wade House Historic Site
The Bull at Pinehurst Farms Golf Course
Hamilton Wood Type and Printing Museum
Stefanie H. Weill Center for the Performing Arts
Harrington Beach State Park

Other Places to Stay in Sheboygan, WI


Sheboygan County 424 Properties
Downtown 181 Properties
Mishicot 139 Properties
Sheboygan Falls 97 Properties
Plymouth 84 Properties
Rhine 83 Properties
Elkhart Lake 83 Properties
Two Rivers 53 Properties
Manitowoc 48 Properties
Chilton 38 Properties
Calumet County 32 Properties
Campbellsport 26 Properties

Frequently Asked Questions About Sheboygan?

What are the top hotels and resorts Sheboygan?

There are a lot of options in Sheboygan. If you plan on staying in the Sheboygan area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Sheboygan:

How many vacation rentals have private pools in Sheboygan?

There are 25 vacation rentals with private pools near Sheboygan. Top-rated Execstays homes that have access to a swimming pool include:

Which vacation homes in Sheboygan are best for families?

If you are looking for a family-friendly vacation home in Sheboygan, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Sheboygan:

How many Execstays vacation rentals are available in Sheboygan?

Currently, the total number of properties listed by Execstays in 2025 is over 803 in the Sheboygan area, and still counting. By aggregating listings from multiple websites, Execstays offers an immense amount of choice of the best Execstays properties in Sheboygan.โ€ฏ

Nearby Neighborhood (3)โ€ฏ
Neighborhood Property Count
Downtown Vacation Rentals in Sheboygan, Wisconsin 181
Ellis Historical District Vacation Rentals in Sheboygan, Wisconsin 201
Raider Vacation Rentals in Sheboygan, Wisconsin 200

People Also Ask

There are 803 Sheboygan, WI Vacation Rentals

Recently Booked Vacation Rentals in Sheboygan