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

Oshawa pickleball Stays, Resort Rentals, & Homes

About Oshawa Vacation Rentals

Discover over 891 amazing vacation rental options in Oshawa 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 Oshawa.

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 1159.35 ft², with prices averaging US $245 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 Oshawa.

Show more
Show less

Top Pickleball-Ready Accommodation Types in Oshawa

Type Count
Vacation Homes 559
Holiday Apartments 188
Cottages 51
Villas 15

Use these Quick Filters to Find a Vacation Rental in Oshawa

★ 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 Oshawa with PickleTrip™.

Weather in Oshawa, ON

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

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


Oshawa Centre
Tribute Communities Centre
Ajax Convention Centre
Skyloft Ski Resort
Rotary Park
Royal Ashburn Golf Club
Goodwood Kartways
Canadian Tire Motorsport Park
Newcastle Memorial Arena
Jungle Cat World Wildlife Park
Airzone
Jungle Cat World Zoo
Lakeridge Health Bowmanville
Creative Play Indoor Playground & Party Centre
Oshawa Valley Botanical Gardens
Whitby History Museum & Children's Centre
Canadian Automotive Museum
Wooden Sticks Golf Course
Uxbridge Historical Centre
Herongate Barn Theatre

Other Places to Stay in Oshawa, ON


Lakeview 120 Properties
Pickering 115 Properties
Whitby 109 Properties
Clarington 101 Properties
Ajax 99 Properties
Uxbridge 99 Properties
Enniskillen 84 Properties
Courtice 74 Properties
Scugog 47 Properties
Bowmanville 46 Properties
Port Perry 33 Properties
Tyrone 27 Properties

Frequently Asked Questions About Oshawa?

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

How many pickleball-ready properties have private pools in Oshawa?

Discover 15 accommodations with private or nearby pickleball courts in Oshawa. Some of the best destinations to stay and play pickleball are:

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

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

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 891 properties listed in Oshawa 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 (2) 
Neighborhood Property Count
Scarborough Vacation Rentals in Oshawa, Ontario 257
Lakeview Vacation Rentals in Oshawa, Ontario 120

People Also Ask

There are 891 Oshawa, ON Vacation Rentals

Recently Booked Vacation Rentals in Oshawa