788+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Sheboygan pickleball Stays, Resort Rentals, & Homes

About Sheboygan Vacation Rentals

Discover over 788 amazing vacation rental options in Sheboygan with pickleball courts or nearby facilities. From resorts to hotels, villas to condos, PickleTrip connects you with a vast selection of pickleball-ready amenities at great prices, providing you with the perfect spot to base your next pickleball vacation. Stay and Play pickleball When You Travel and uncover great stays in Sheboygan.

Find exclusive last-minute deals on vacation rentals, resorts, and hotels with private courts and nearby facilities with PickleTrip™, whether you're traveling solo or with a group. Our platform offers a variety of stay options, from vacation rentals to Airbnb-style properties, all with private pickleball courts or nearby facilities. Compare options from multiple suppliers with a single click to find the perfect stay that fits your budget and style. Places to stay near pickleball courts are an average of 858.88 ft², with prices averaging US $414 per night.

With PickleTrip™, you can easily search for and book your next pickleball vacation rental with courts or nearby facilities. Our platform connects you with the ideal holiday rental to create a lifetime of travel memories. Prices listed are often discounted versus rack rates, so you can secure your perfect place to stay today and get ready to play pickleball in Sheboygan.

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Top Pickleball-Ready Accommodation Types in Sheboygan

Type Count
Vacation Homes 404
Holiday Apartments 140
Villas 31
Cottages 23

Use these Quick Filters to Find a Vacation Rental in Sheboygan

★ Pro Tip: PickleTrip™ is a travel platform, connecting avid pickleball players and enthusiasts with a variety of vacation rentals, resorts, and hotels featuring private pickleball courts or nearby facilities. We curate a vast selection of properties from trusted sources, providing you with unbeatable options and pricing to find the perfect pickleball getaway. Experience unforgettable pickleball matches in Sheboygan with PickleTrip™.

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

Top Attractions Around Sheboygan, WI

PickleTrip 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 554 Properties
Downtown 235 Properties
Ellis Historical District 201 Properties
Rhine 114 Properties
Elkhart Lake 114 Properties
Plymouth 107 Properties
Sheboygan Falls 97 Properties
Two Rivers 72 Properties
Manitowoc 66 Properties
Calumet County 44 Properties
Chilton 38 Properties
Campbellsport 36 Properties

Frequently Asked Questions About Sheboygan?

What are the top vacation rentals, resorts, and hotels in Sheboygan with Courts?

Experience the ultimate pickleball vacation with PickleTrip™. We offer a variety of premium rental properties, resorts, and hotels with private pickleball courts or nearby facilities in Sheboygan. Whether you're a beginner or a seasoned player, we have the perfect destination for you to stay and play. Book now and discover the best pickleball vacation spots in Sheboygan!

How many pickleball-ready properties have private pools in Sheboygan?

Discover 29 accommodations with private or nearby pickleball courts in Sheboygan. Some of the best destinations to stay and play pickleball are:

Which vacation rentals, resorts, or hotels in Sheboygan is best for families looking for a pickleball-getaway?

Looking for a fun and active getaway with pickleball courts in Sheboygan? With PickleTrip™, you'll have access to a wide selection of top-rated properties that offer private pickleball courts or nearby facilities. Make the most of you getaway and ace your A-game while you travel.

How many PickleTrip vacation rentals or resorts are available in Sheboygan?

PickleTrip™ offers a diverse selection of properties with private pickleball courts or nearby facilities to enhance your pickleball experience on your next trip. With a combination of established great stays and new options in top locations, PickleTrip™ has over 788 properties listed in Sheboygan in 2025, and the number only continues to grow. By consolidating listings from various providers, PickleTrip™ brings you the best luxury stays for a sporty, professional, and fun travel experience.

Nearby Neighborhood (3) 
Neighborhood Property Count
Downtown Vacation Rentals in Sheboygan, Wisconsin 235
Ellis Historical District Vacation Rentals in Sheboygan, Wisconsin 201
Raider Vacation Rentals in Sheboygan, Wisconsin 200

People Also Ask

There are 788 Sheboygan, WI Vacation Rentals

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