709+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Madison pickleball Stays, Resort Rentals, & Homes

About Madison Vacation Rentals

Discover over 709 amazing vacation rental options in Madison 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 Madison.

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 651.61 ft², with prices averaging US $303 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 Madison.

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Top Pickleball-Ready Accommodation Types in Madison

Type Count
Vacation Homes 273
Holiday Apartments 122
Cottages 22
Villas 3

Use these Quick Filters to Find a Vacation Rental in Madison

★ 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 Madison with PickleTrip™.

Weather in Madison, WI

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

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


University of Wisconsin-Madison
Alliant Energy Center
Kohl Center
Wisconsin State Capitol
East Towne Mall
Ho-Chunk Gaming Madison
Capitol Square
Camp Randall Stadium
Overture Center for the Arts
University of Wisconsin Hospital and Clinics
Madison Area Technical College
New Glarus Brewing Company
Orpheum Theater
Barrymore Theatre
Monona Terrace Community and Convention Center
Lake Mendota
Olbrich Botanical Gardens
West Towne Mall
Henry Vilas Zoo
Tyrol Basin Ski & Snowboard Area

Other Places to Stay in Madison, WI


Dane County 698 Properties
Downtown Madison 363 Properties
State Street Shopping 363 Properties
Mount Horeb 50 Properties
Middleton 48 Properties
Sun Prairie 44 Properties
Monona 39 Properties
Lodi 39 Properties
Beaver Dam 35 Properties
Verona 26 Properties
Cambridge 26 Properties
Lake Ripley 25 Properties

Frequently Asked Questions About Madison?

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

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

Discover 69 accommodations with private or nearby pickleball courts in Madison. Some of the best destinations to stay and play pickleball are:

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

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

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 709 properties listed in Madison 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 (14) 
Neighborhood Property Count
Marquette Vacation Rentals in Madison, Wisconsin 172
Tenney-Lapham Vacation Rentals in Madison, Wisconsin 161
Regent Vacation Rentals in Madison, Wisconsin 148
Spring Harbor Vacation Rentals in Madison, Wisconsin 139
Bay Creek Vacation Rentals in Madison, Wisconsin 178
Shorewood Hills Vacation Rentals in Madison, Wisconsin 86
Waubesa Beach Vacation Rentals in Madison, Wisconsin 35
North Lake Mendota Vacation Rentals in Madison, Wisconsin 274
Greenbush Vacation Rentals in Madison, Wisconsin 161
Emerson East Vacation Rentals in Madison, Wisconsin 134
Lakeview Vacation Rentals in Madison, Wisconsin 111
Middleton Springs Vacation Rentals in Madison, Wisconsin 98
Eagle Heights Assembly Vacation Rentals in Madison, Wisconsin 90
Meadowood Vacation Rentals in Madison, Wisconsin 71

People Also Ask

There are 709 Madison, WI Vacation Rentals

Recently Booked Vacation Rentals in Madison