229+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. Canada
  2. Ontario
  3. Oshawa
  4. Pickering

Pickering pickleball Stays, Resort Rentals, & Homes

About Pickering Vacation Rentals

Discover over 229 amazing vacation rental options in Pickering 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 Pickering.

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 461.43 ft², with prices averaging US $191 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 Pickering.

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Top Pickleball-Ready Accommodation Types in Pickering

Type Count
Vacation Homes 158
Holiday Apartments 48
Villas 6

Use these Quick Filters to Find a Vacation Rental in Pickering

★ 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 Pickering with PickleTrip™.

Weather in Pickering, ON

View the weather forecast for Pickering before booking your Pickering Vacation Rentals to confirm your best time to go.

December - February
High 23°F       Low 2°F
March - May
High 65°F       Low 12°F
June - August
High 76°F       Low 49°F
September - November
High 65°F       Low 8°F

Top Attractions Around Pickering, ON

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


Herongate Barn Theatre
Deer Creek North Golf Course
Glen Cedars Golf Club
Luke Andrews Wood Sculptures
AnNonedale Golf and Country Club
CN Tower
Toronto Eaton Centre
Canada's Wonderland
Rogers Centre
Scotiabank Arena
Ripley's Aquarium of Canada
Metro Toronto Convention Centre
Royal Ontario Museum
Toronto Zoo
Casa Loma
Vaughan Mills Mall
University of Toronto - St. George Campus
Royal Alexandra Theatre
Hockey Hall of Fame
Harbourfront Centre

Other Places to Stay in Pickering, ON


Luke Andrews Wood Sculptures 680 Properties
Annandale Golf and Country Club 221 Properties
Glen Cedars Golf Club 105 Properties
Deer Creek North Golf Course 32 Properties
Herongate Barn Theatre 28 Properties

Frequently Asked Questions About Pickering?

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

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

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

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 229 properties listed in Pickering 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
Scarborough Vacation Rentals in Oshawa, Ontario 254

People Also Ask

There are 229 Pickering, ON Vacation Rentals

Recently Booked Vacation Rentals in Pickering