96+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  2. Illinois
  3. Chicago
  4. Old Town Triangle

Old Town Triangle pickleball Stays, Resort Rentals, & Homes

About Old Town Triangle Vacation Rentals

Discover over 96 amazing vacation rental options in Old Town Triangle 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 Old Town Triangle.

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 1267.61 ft², with prices averaging $549 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 Old Town Triangle.

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Top Pickleball-Ready Accommodation Types in Old Town Triangle

Type Count
Vacation Homes 39
Holiday Apartments 38

Use these Quick Filters to Find a Vacation Rental in Old Town Triangle

★ 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 Old Town Triangle with PickleTrip™.

Weather in Old Town Triangle, IL

View the weather forecast for Old Town Triangle before booking your Old Town Triangle 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

Other Places to Stay in Old Town Triangle, IL


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Frequently Asked Questions About Old Town Triangle?

What are the top vacation rentals, resorts, and hotels in Old Town Triangle 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 Old Town Triangle. 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 Old Town Triangle!

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

Looking for a fun and active getaway with pickleball courts in ? 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 Old Town Triangle?

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 96 properties listed in Old Town Triangle 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 (5) 
Neighborhood Property Count
Downtown Chicago Vacation Rentals in Chicago, Illinois 1706
Near North Side Vacation Rentals in Chicago, Illinois 785
Lincoln Park Vacation Rentals in Chicago, Illinois 158
Old Town Vacation Rentals in Chicago, Illinois 51
Mid-North District Vacation Rentals in Chicago, Illinois 24

People Also Ask

There are 96 Old Town Triangle, IL Vacation Rentals

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