612+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Wisconsin
  3. Sherwood

Sherwood pickleball Stays, Resort Rentals, & Homes

About Sherwood Vacation Rentals

Discover over 612 amazing vacation rental options in Sherwood 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 Sherwood.

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 805.11 ft², with prices averaging US $400 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 Sherwood.

Show more
Show less

Top Pickleball-Ready Accommodation Types in Sherwood

Type Count
Vacation Homes 365
Holiday Apartments 146
Cottages 9
Villas 2

Use these Quick Filters to Find a Vacation Rental in Sherwood

★ 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 Sherwood with PickleTrip™.

Weather in Sherwood, WI

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

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


Harrison Military Trail
EAA AirVenture Museum
Fox River Mall
University of Wisconsin-Oshkosh
Lake Winnebago
Fox Valley Technical College
Fox Cities Performing Arts Center
Lawrence University
Menominee Park
Appleton Medical Center
Radisson Paper Valley Conference Center
Appleton Memorial Park
Menominee Nation Arena
Grand Opera House
Titan Stadium
University of Wisconsin-Fox Valley
Erb Park
Telulah Park
Chilton Speedway
Plamann Park

Other Places to Stay in Sherwood, WI


Harrison Military Trail 547 Properties

Frequently Asked Questions About Sherwood?

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

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

Discover 25 accommodations with private or nearby pickleball courts in Sherwood. Some of the best destinations to stay and play pickleball are:

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

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

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 612 properties listed in Sherwood 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 612 Sherwood, WI Vacation Rentals

Recently Booked Vacation Rentals in Sherwood