802+ Vacation Rentals & Holiday Homes in Sheboygan |
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Sheboygan Accommodations - Hotels & Rentals

About Sheboygan Vacation Rentals

Discover More than 802 Incredible Getaway Rentals Available in Sheboygan. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Sheboygan.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Sheboygan, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Sheboygan. The Average Size of Places to Stay Near Sheboygan is 849.76 ft², with Prices Averaging US $413 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Sheboygan. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals in Sheboygan

Type Count
Vacation Homes 410
Holiday Apartments 140
Villas 31
Cottages 24

Use these Quick Filters to Find a Vacation Rental in Sheboygan

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Sheboygan with Online Reservations.

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 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Activities SheboyganGuest Reviews Local Attractions

A Large Selection of Hotels and Vacation Rentals from Around the World SheboyganGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey


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

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


Sheboygan County 398 Properties
Ellis Historical District 228 Properties
Downtown 172 Properties
Sheboygan Falls 91 Properties
Plymouth 81 Properties
Rhine 73 Properties
Elkhart Lake 73 Properties
Chilton 68 Properties
Two Rivers 55 Properties
Manitowoc 43 Properties
Calumet County 38 Properties
Campbellsport 25 Properties

Frequently Asked Questions About Sheboygan?

What are the top hotels, lake houses & vacation rentals in Sheboygan?

We provide an array of great vacation destinations in Sheboygan. If you are looking to stay in or around the Sheboygan area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Sheboygan:

How many Hotels & Vacation Rentals have private pools in Sheboygan?

We have 28 Hotels & Vacation Rentals featuring a private pool in and near Sheboygan. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which hotel, lake house, or vacation rental in Sheboygan is best for families?

Searching for a family-friendly getaway in Sheboygan? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Sheboygan?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2026 is over 802 in the Sheboygan area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Sheboygan.

Nearby Neighborhood (3) 
Neighborhood Property Count
Downtown Vacation Rentals in Sheboygan, Wisconsin 172
Ellis Historical District Vacation Rentals in Sheboygan, Wisconsin 228
Raider Vacation Rentals in Sheboygan, Wisconsin 231

People Also Ask

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