148+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Sherman pickleball Stays, Resort Rentals, & Homes

About Sherman Vacation Rentals

Discover over 148 amazing vacation rental options in Sherman 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 Sherman.

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 1103.3 ft², with prices averaging US $556 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 Sherman.

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Top Pickleball-Ready Accommodation Types in Sherman

Type Count
Vacation Homes 82
Cottages 15
Holiday Apartments 11

Use these Quick Filters to Find a Vacation Rental in Sherman

★ 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 Sherman with PickleTrip™.

Weather in Sherman, WI

View the weather forecast for Sherman before booking your Sherman 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 Sherman, WI

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


Whistling Straits Golf Course
Blue Harbor Resort & Conference Center Water Park
Road America
Kettle Moraine State Forest
Sunburst Ski Area
Cedarburg Cultural Center
Kohler Design Center
Blackwolf Run
Skip Barber Driving School
Kohler-Andrae State Park
John Michael Kohler Arts Center
Washington County Fair Grounds
University of Wisconsin-Sheboygan
Little Switzerland
Nicky Boy Charters
St. Peter Claver Parish
Children's Museum
Wade House Historic Site
Shalom Wildlife
1860 Light Station and Museum
The Bull at Pinehurst Farms Golf Course
Regner Park
Cedar Creek Settlement
Stefanie H. Weill Center for the Performing Arts
Ozaukee Interurban Trail
Port Washington Ghost Walk
Harrington Beach State Park
Evans
Covered Bridge
Fox Hill Ski Area

Other Places to Stay in Sherman, WI


Adell 174 Properties
Random Lake 107 Properties

Frequently Asked Questions About Sherman?

What are the top vacation rentals, resorts, and hotels in Sherman 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 Sherman. 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 Sherman!

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

Discover 2 accommodations with private or nearby pickleball courts in Sherman. Some of the best destinations to stay and play pickleball are:

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

Looking for a fun and active getaway with pickleball courts in Sherman? 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 Sherman?

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 148 properties listed in Sherman 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.


People Also Ask

There are 148 Sherman, WI Vacation Rentals

Recently Booked Vacation Rentals in Sherman