1208+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Illinois
  3. Chicago
  4. North Side

North Side pickleball Stays, Resort Rentals, & Homes

About North Side Vacation Rentals

Discover over 1208 amazing vacation rental options in North Side 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 North Side.

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 860.69 ft², with prices averaging $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 North Side.

Show more
Show less

Top Pickleball-Ready Accommodation Types in North Side

Type Count
Holiday Apartments 756
Vacation Homes 244
Cottages 1

Use these Quick Filters to Find a Vacation Rental in North Side

★ 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 North Side with PickleTrip™.

Weather in North Side, IL

View the weather forecast for North Side before booking your North Side 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 North Side, IL

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


Wrigley Field
Lincoln Park Zoo
Vic Theatre
Concord Music Hall
Chicago History Museum
Second City
DePaul University-Lincoln Park
Briar Street Theatre
Lincoln Hall
Park West
Apollo Theater Chicago
Athenaeum Theatre
Theater Wit
Advocate Illinois Masonic Medical Center
Kingston Mines
Saint Joseph Hospital
Lincoln Park
Royal George Theater
Peggy Notebaert Nature Museum
Steppenwolf Theatre

Other Places to Stay in North Side, IL


Lakeview 265 Properties
Lincoln Park 158 Properties
Logan Square 78 Properties
Lake View East 73 Properties
North Center 70 Properties
Old Town 51 Properties
Old Town Triangle 51 Properties
Sheffield and DePaul 44 Properties
Wrigleyville 44 Properties
Avondale 44 Properties
West Bucktown 35 Properties
Wrightwood Neighbors 29 Properties

Frequently Asked Questions About North Side?

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

How many pickleball-ready properties have private pools in North Side?

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

Which vacation rentals, resorts, or hotels in North Side 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 North Side?

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 1208 properties listed in North Side 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 (16) 
Neighborhood Property Count
Downtown Chicago Vacation Rentals in Chicago, Illinois 1703
Near North Side Vacation Rentals in Chicago, Illinois 785
River North Vacation Rentals in Chicago, Illinois 434
West Town Vacation Rentals in Chicago, Illinois 315
Lakeview Vacation Rentals in Chicago, Illinois 265
Lincoln Park Vacation Rentals in Chicago, Illinois 158
Logan Square Vacation Rentals in Chicago, Illinois 78
Lake View East Vacation Rentals in Chicago, Illinois 73
North Center Vacation Rentals in Chicago, Illinois 70
Gold Coast Vacation Rentals in Chicago, Illinois 54
Old Town Vacation Rentals in Chicago, Illinois 51
Wicker Park Vacation Rentals in Chicago, Illinois 50
Irving Park Vacation Rentals in Chicago, Illinois 47
Wrigleyville Vacation Rentals in Chicago, Illinois 44
Avondale Vacation Rentals in Chicago, Illinois 44
Uptown Vacation Rentals in Chicago, Illinois 36

People Also Ask

There are 1208 North Side, IL Vacation Rentals

Recently Booked Vacation Rentals in North Side