68+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  2. Wisconsin
  3. Milwaukee
  4. Oconomowoc

Oconomowoc pickleball Stays, Resort Rentals, & Homes

About Oconomowoc Vacation Rentals

Discover over 68 amazing vacation rental options in Oconomowoc 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 Oconomowoc.

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 1525.7 ft², with prices averaging US $757 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 Oconomowoc.

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Top Pickleball-Ready Accommodation Types in Oconomowoc

Type Count
Vacation Homes 36
Holiday Apartments 6
Cottages 3
Villas 1

Use these Quick Filters to Find a Vacation Rental in Oconomowoc

★ 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 Oconomowoc with PickleTrip™.

Weather in Oconomowoc, WI

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

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


Lac La Belle
Oconomowoc Arts Center
Imagination Station
Fowler Lake Park
Oconomowoc Gallery
Oconomowoc Golf Club
AKA Combat Entertainment
Theatre On Main
Knollward
Point Comfort Okauchee
Oakbrook-Eser Studios and Gallery
Oconomowoc Masonic Center
Oconomowoc Historical Museum
Oconomowoc Memorial Hospital
Aurora Medical Center Summit
Alpine Valley Ski Resort
Alpine Valley Music Theatre
University of Wisconsin-Whitewater
Fireside Dinner Theatre
Jefferson County Fairgrounds

Other Places to Stay in Oconomowoc, WI


Hillside Park Merton 87 Properties
Stonebank 82 Properties
Davies Plateau 74 Properties
Hayburn Heights 73 Properties
Peninsular Park 69 Properties
AKA Combat Entertainment 66 Properties
Lac La Belle 66 Properties
Summit Corners 55 Properties
Maplewood 42 Properties
Oconomowoc Lake 41 Properties
Summit 35 Properties
Okauchee Lake 31 Properties

Frequently Asked Questions About Oconomowoc?

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

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

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

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 68 properties listed in Oconomowoc 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 (7) 
Neighborhood Property Count
Maplewood Vacation Rentals in Milwaukee, Wisconsin 42
Peninsular Park Vacation Rentals in Milwaukee, Wisconsin 69
Hillside Park Merton Vacation Rentals in Milwaukee, Wisconsin 87
Davies Plateau Vacation Rentals in Milwaukee, Wisconsin 74
Hayburn Heights Vacation Rentals in Milwaukee, Wisconsin 73
Breens Bay Vacation Rentals in Milwaukee, Wisconsin 63
Bauers Bays Vacation Rentals in Milwaukee, Wisconsin 30

People Also Ask

There are 68 Oconomowoc, WI Vacation Rentals

Recently Booked Vacation Rentals in Oconomowoc