24244+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Wisconsin pickleball Stays, Resort Rentals, & Homes

About Wisconsin Vacation Rentals

Discover over 24244 amazing vacation rental options in Wisconsin 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 Wisconsin.

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 961.58 ft², with prices averaging US $408 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 Wisconsin.

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Things to Know Before You Visit Wisconsin

Wisconsin is the Midwests most underrated travel destination. That might be because it doesnu2019t offer stereotypical travel wants like the beaches of Florida or California, but that doesnt mean you should sleep on this travel gem!

Madison, Wisconsin: The City of Four Lakes
This charming college town has everything a traveler needs! Major draws to the city include the University of Wisconsin, beautiful lakes (hence the name) and tons of vegan food. There are also fun outdoor activities like biking trails, hiking in the nearby state parks and even skiing in the winter. The city is also very walkable if you prefer to see it all on foot.

Milwaukee, Wisconsin: Brew City
Milwaukee is known for its breweries. The city has the highest number of breweries per capita in the US and its easy to see why! Milwaukee has a lot of fun things to do. For example, check out an art museum or walk around downtown at night when they have free concerts in the summertime.

Appleton, Wisconsin: A Place Worth Visiting
This small city often gets overshadowed by other cities in the state, but its definitely worth a visit! If you love nature, head to the nearby Appleton-Fox River State Recreational Area for some hiking in the beautiful north woods and kayaking in the Fox River.

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Top Pickleball-Ready Accommodation Types in Wisconsin

Type Count
Vacation Homes 11354
Holiday Apartments 2960
Cottages 1280
Villas 199

Use these Quick Filters to Find a Vacation Rental in Wisconsin

★ 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 Wisconsin with PickleTrip™.

Weather in Wisconsin, US

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

December - February
High 37°F       Low 11°F
March - May
High 62°F       Low 22°F
June - August
High 79°F       Low 57°F
September - November
High 73°F       Low 26°F

Top Attractions Around Wisconsin, US

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


Kalahari Indoor Waterpark
Lambeau Field
University of Wisconsin-Madison
Miller Park
Fiserv Forum
Ho-Chunk Casino
Noah's Ark Waterpark
University of Wisconsin-Milwaukee
Harley-Davidson Museum
Alliant Energy Center
Top Secret
Resch Center
Kohl Center
The Rave-Eagles Club
Wisconsin Center
Kalahari Waterparks
Mt. Olympus Water and Theme Park
Marquette University
Cascade Mountain Ski Area
Riverside Theater
Granite Peak Ski Area
Milwaukee Public Museum
La Crosse Center
Potawatomi Bingo Casino
Pabst Theater
Oneida Casino
EAA AirVenture Museum
Mayfair Mall
Milwaukee Art Museum
Alpine Valley Ski Resort

Other Places to Stay in Wisconsin, US


Northern Wisconsin 10,171 Properties
Southern Wisconsin 9,818 Properties
Central Wisconsin 9,344 Properties
Rhinelander 2,266 Properties
Milwaukee 2,132 Properties
Wisconsin Dells 1,773 Properties
Vilas County 1,738 Properties
Door County 1,556 Properties
Milwaukee County 1,382 Properties
Lake Geneva 953 Properties
Sauk County 929 Properties
Walworth County 921 Properties

Frequently Asked Questions About Wisconsin?

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

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

Discover 929 accommodations with private or nearby pickleball courts in Wisconsin. Some of the best destinations to stay and play pickleball are:

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

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

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 24244 properties listed in Wisconsin 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 24244 Wisconsin, US Vacation Rentals

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