25+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Fennimore pickleball Stays, Resort Rentals, & Homes

About Fennimore Vacation Rentals

Discover over 25 amazing vacation rental options in Fennimore 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 Fennimore.

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 320.23 ft², with prices averaging US $168 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 Fennimore.

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Top Pickleball-Ready Accommodation Types in Fennimore

Type Count
Vacation Homes 9
Holiday Apartments 3

Use these Quick Filters to Find a Vacation Rental in Fennimore

★ 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 Fennimore with PickleTrip™.

Weather in Fennimore, WI

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

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


Carr Valley Cheese
Whispering Winds Winery
Fennimore Doll and Toy Museum
Fennimore Railroad Historical Society Museum
University of Wisconsin-Platteville
Governor Dodge State Park
Wyalusing State Park
WI River Outings
Mineral Point Railroad Museum
Eagle Cave
Mining Museum
Nelson Dewey State Park
Pendarvis
Kickapoo River
Blackhawk Lake Recreation Area
Charles Wacouta Aquatic Park
Fort Fun Park
Rollo Jamison Museum
National Brewery Museum
Alley Stage

Other Places to Stay in Fennimore, WI


Whispering Winds Winery 55 Properties
Fennimore Doll and Toy Museum 24 Properties
Fennimore Railroad Historical Society Museum 24 Properties
Carr Valley Cheese 24 Properties

Frequently Asked Questions About Fennimore?

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

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

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 25 properties listed in Fennimore 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.


People Also Ask

There are 25 Fennimore, WI Vacation Rentals

Recently Booked Vacation Rentals in Fennimore