183+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  2. Ontario
  3. Oshawa
  4. Whitby

Whitby pickleball Stays, Resort Rentals, & Homes

About Whitby Vacation Rentals

Discover over 183 amazing vacation rental options in Whitby 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 Whitby.

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 1011.44 ft², with prices averaging US $200 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 Whitby.

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Top Pickleball-Ready Accommodation Types in Whitby

Type Count
Vacation Homes 121
Holiday Apartments 46
Cottages 3
Villas 2

Use these Quick Filters to Find a Vacation Rental in Whitby

★ 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 Whitby with PickleTrip™.

Weather in Whitby, ON

View the weather forecast for Whitby before booking your Whitby 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 Whitby, ON

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


Royal Ashburn Golf Club
Whitby History Museum & Children's Centre
Lynde Shores Conservation Area
Toronto Zoo
Scarborough Town Centre
Oshawa Centre
Centennial College
Flato Markham Theatre
University of Toronto Scarborough
Tribute Communities Centre
Markham Pan Am Centre
Lake Ontario
Guild Inn Gardens
Pacific Mall
Ajax Convention Centre
Scarborough Bluffs Park
Angus Glen Golf Club
Markham Museum
Great Blue Heron Charity Casino
Skyloft Ski Resort

Other Places to Stay in Whitby, ON


Whitby History Museum & Children's Centre 147 Properties
Lynde Shores Conservation Area 114 Properties
Royal Ashburn Golf Club 42 Properties
Brooklin 37 Properties

Frequently Asked Questions About Whitby?

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

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

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

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 183 properties listed in Whitby 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.


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There are 183 Whitby, ON Vacation Rentals

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