35+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  3. Madison
  4. Middleton

Middleton pickleball Stays, Resort Rentals, & Homes

About Middleton Vacation Rentals

Discover over 35 amazing vacation rental options in Middleton 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 Middleton.

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 491.09 ft², with prices averaging US $253 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 Middleton.

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Top Pickleball-Ready Accommodation Types in Middleton

Type Count
Vacation Homes 6
Holiday Apartments 5

Use these Quick Filters to Find a Vacation Rental in Middleton

★ 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 Middleton with PickleTrip™.

Weather in Middleton, WI

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

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


National Mustard Museum
Capital Brewery
Pleasant View Golf Course
Death's Door Spirits Distillery
University of Wisconsin-Madison
Alliant Energy Center
Kohl Center
Devil's Head Ski Resort
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
Orpheum Theater
Devil's Lake State Park
Barrymore Theatre
Monona Terrace Community and Convention Center

Other Places to Stay in Middleton, WI


Lakeview 79 Properties
National Mustard Museum 76 Properties
Capital Brewery 75 Properties
Middleton Springs 65 Properties
Death's Door Spirits Distillery 59 Properties
Pleasant View Golf Course 55 Properties

Frequently Asked Questions About Middleton?

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

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

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

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 35 properties listed in Middleton 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 (2) 
Neighborhood Property Count
Lakeview Vacation Rentals in Madison, Wisconsin 79
Middleton Springs Vacation Rentals in Madison, Wisconsin 65

People Also Ask

There are 35 Middleton, WI Vacation Rentals

Recently Booked Vacation Rentals in Middleton