31+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  2. Wisconsin
  3. Milwaukee
  4. Pewaukee

Pewaukee pickleball Stays, Resort Rentals, & Homes

About Pewaukee Vacation Rentals

Discover over 31 amazing vacation rental options in Pewaukee 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 Pewaukee.

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 731.23 ft², with prices averaging US $409 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 Pewaukee.

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Top Pickleball-Ready Accommodation Types in Pewaukee

Type Count
Vacation Homes 21
Villas 1

Use these Quick Filters to Find a Vacation Rental in Pewaukee

★ 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 Pewaukee with PickleTrip™.

Weather in Pewaukee, WI

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

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


Springs Water Park
Pewaukee Lake Beach
Two Brothers Wines
Miller Park
Fiserv Forum
University of Wisconsin-Milwaukee
Harley-Davidson Museum
The Rave-Eagles Club
Wisconsin Center
Marquette University
Riverside Theater
Milwaukee Public Museum
Potawatomi Bingo Casino
Pabst Theater
Mayfair Mall
Milwaukee Art Museum
Milwaukee County Zoo
Milwaukee RiverWalk
Milwaukee Public Market
Wisconsin State Fair Park

Other Places to Stay in Pewaukee, WI


Springs Water Park 46 Properties
Lakeview 41 Properties
Village of Pewaukee 38 Properties
Two Brothers Wines 38 Properties
Pewaukee Lake Beach 38 Properties
Five Fields 24 Properties

Frequently Asked Questions About Pewaukee?

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

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

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 31 properties listed in Pewaukee in 2026, 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
Lakeview Vacation Rentals in Milwaukee, Wisconsin 41
Starke Peninsula Vacation Rentals in Milwaukee, Wisconsin 40
Five Fields Vacation Rentals in Milwaukee, Wisconsin 24

People Also Ask

There are 31 Pewaukee, WI Vacation Rentals

Recently Booked Vacation Rentals in Pewaukee