103+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Wisconsin
  3. Sheboygan
  4. Plymouth

Plymouth pickleball Stays, Resort Rentals, & Homes

About Plymouth Vacation Rentals

Discover over 103 amazing vacation rental options in Plymouth 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 Plymouth.

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 1092.42 ft², with prices averaging US $480 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 Plymouth.

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Top Pickleball-Ready Accommodation Types in Plymouth

Type Count
Vacation Homes 60
Holiday Apartments 20
Cottages 4
Villas 2

Use these Quick Filters to Find a Vacation Rental in Plymouth

★ 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 Plymouth with PickleTrip™.

Weather in Plymouth, WI

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

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


Road America
Skip Barber Driving School
Antoinette
Evergreen Golf Course
Sheboygan County Fairgrounds
Whistling Straits Golf Course
Blue Harbor Resort & Conference Center Water Park
Lake Winnebago
Kettle Moraine State Forest
Lakeside Park
Sunburst Ski Area
Kohler Design Center
Blackwolf Run
Kohler-Andrae State Park
John Michael Kohler Arts Center
University of Wisconsin-Sheboygan
Chilton Speedway
Children's Museum of Fond du Lac
St. Peter Claver Parish
Children's Museum

Other Places to Stay in Plymouth, WI


Sheboygan County 554 Properties
Skip Barber Driving School 137 Properties
Road America 134 Properties
Antoinette 34 Properties
Sheboygan County Fairgrounds 32 Properties
Evergreen Golf Course 29 Properties

Frequently Asked Questions About Plymouth?

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

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

Discover 1 accommodations with private or nearby pickleball courts in Plymouth. Some of the best destinations to stay and play pickleball are:

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

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

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 103 properties listed in Plymouth 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.


People Also Ask

There are 103 Plymouth, WI Vacation Rentals

Recently Booked Vacation Rentals in Plymouth