53+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Indiana
  3. Chesterton

Chesterton pickleball Stays, Resort Rentals, & Homes

About Chesterton Vacation Rentals

Discover over 53 amazing vacation rental options in Chesterton 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 Chesterton.

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 1271.15 ft², with prices averaging US $247 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 Chesterton.

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Top Pickleball-Ready Accommodation Types in Chesterton

Type Count
Vacation Homes 24
Holiday Apartments 11
Cottages 7

Use these Quick Filters to Find a Vacation Rental in Chesterton

★ 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 Chesterton with PickleTrip™.

Weather in Chesterton, IN

View the weather forecast for Chesterton before booking your Chesterton 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 Chesterton, IN

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


Indiana Dunes State Park
Indiana Dunes National Park
Lustron House
Waverly Beach
Coffee Creek Watershed Conservancy Preserve
Blue Chip Casino
Ameristar Casino East Chicago
Local
Valparaiso University
Deep River Water Park
Majestic Star Casino
Lighthouse Place Premium Outlets
Harrah's East Chicago Casino
New Buffalo Public Beach
Purdue University Northwest
Trail Creek
Crown Point Sports Complex
Marquette Park
Albanese Candy Factory
Oasis Splash Pad

Other Places to Stay in Chesterton, IN


Waverly Beach 95 Properties
Lustron House 64 Properties
Indiana Dunes National Park 62 Properties
Indiana Dunes State Park 54 Properties
Coffee Creek Watershed Conservancy Preserve 53 Properties
Porter Beach 29 Properties

Frequently Asked Questions About Chesterton?

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

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

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

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 53 properties listed in Chesterton 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 (1) 
Neighborhood Property Count
Porter Beach Vacation Rentals in Chesterton, Indiana 29

People Also Ask

There are 53 Chesterton, IN Vacation Rentals

Recently Booked Vacation Rentals in Chesterton