648+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  2. Iowa
  3. Dickinson County

Dickinson County pickleball Stays, Resort Rentals, & Homes

About Dickinson County Vacation Rentals

Discover over 648 amazing vacation rental options in Dickinson County 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 Dickinson County.

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 948.55 ft², with prices averaging US $420 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 Dickinson County.

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Top Pickleball-Ready Accommodation Types in Dickinson County

Type Count
Vacation Homes 263
Villas 41
Holiday Apartments 40
Cottages 27

Use these Quick Filters to Find a Vacation Rental in Dickinson County

★ 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 Dickinson County with PickleTrip™.

Weather in Dickinson County, IA

View the weather forecast for Dickinson County before booking your Dickinson County 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 Dickinson County, IA

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


West Okoboji Lake
Arnolds Park
'Boji Splash Indoor Waterpark Okoboji
Emerald Hills Golf Course
East Okoboji Lake
Okoboji Summer Theatre
Little Swan Lake Winery
Brooks Golf Club
Iowa Great Lakes Maritime Museum
Pike's Point Beach
Goodies Handmade Candies
Ranch Okoboji
Higgins Museum
Lakes Regional Healthcare

Other Places to Stay in Dickinson County, IA


Lake Park 606 Properties
Lakeville 519 Properties
Okoboji 517 Properties
Iowa Great Lakes 416 Properties
Center Grove 391 Properties
West Okoboji Lake 227 Properties
Arnolds Park 204 Properties
Spirit Lake 189 Properties
East Okoboji Lake 170 Properties
Orleans 85 Properties
West Okoboji 35 Properties
Milford 35 Properties

Frequently Asked Questions About Dickinson County?

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

How many pickleball-ready properties have private pools in Dickinson County?

Discover 65 accommodations with private or nearby pickleball courts in Dickinson County. Some of the best destinations to stay and play pickleball are:

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

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

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 648 properties listed in Dickinson County 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 648 Dickinson County, IA Vacation Rentals

Recently Booked Vacation Rentals in Dickinson County