2766+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  3. Owen Sound

Owen Sound pickleball Stays, Resort Rentals, & Homes

About Owen Sound Vacation Rentals

Discover over 2766 amazing vacation rental options in Owen Sound 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 Owen Sound.

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 1178.53 ft², with prices averaging $349 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 Owen Sound.

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Top Pickleball-Ready Accommodation Types in Owen Sound

Type Count
Vacation Homes 937
Cottages 484
Holiday Apartments 267
Villas 11

Use these Quick Filters to Find a Vacation Rental in Owen Sound

★ 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 Owen Sound with PickleTrip™.

Weather in Owen Sound, ON

View the weather forecast for Owen Sound before booking your Owen Sound 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 Owen Sound, ON

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


Blue Mountain Ski Resort
Blue Mountain Village
Bruce Peninsula
Scandinave Spa Blue Mountain
Collingwood Scenic Caves
Bruce Peninsula National Park
Blue Mountain Beach
Cyprus Lake
Village at Blue
Beaver Valley Ski Club
Inglis Falls
Ridge Runner Mountain Coaster
Plunge Aquatic Center
Georgian College Owen Sound Campus
Harry Lumley Bayshore Community Centre
Sauble Falls Provincial Park
Bruce Power Visitors' Centre
Craigleith Provincial Park
Fathom Five National Marine Park
Georgian Hills Vineyards

Other Places to Stay in Owen Sound, ON


Grey County 1,381 Properties
The Blue Mountains 1,098 Properties
Bruce Peninsula 501 Properties
Northern Bruce Peninsula 300 Properties
Craigleith 261 Properties
South Bruce Peninsula 194 Properties
Saugeen Shores 142 Properties
Miller Lake 112 Properties
Wiarton 112 Properties
Grey Highlands 106 Properties
Tobermory 104 Properties
Lion's Head 82 Properties

Frequently Asked Questions About Owen Sound?

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

How many pickleball-ready properties have private pools in Owen Sound?

Discover 69 accommodations with private or nearby pickleball courts in Owen Sound. Some of the best destinations to stay and play pickleball are:

Which vacation rentals, resorts, or hotels in Owen Sound 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 Owen Sound?

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 2766 properties listed in Owen Sound 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 (4) 
Neighborhood Property Count
Craigleith Vacation Rentals in Owen Sound, Ontario 261
Swiss Meadows Vacation Rentals in Owen Sound, Ontario 236
Castle Glen Estates Vacation Rentals in Owen Sound, Ontario 52
Nipissing Ridge Vacation Rentals in Owen Sound, Ontario 1217

People Also Ask

There are 2766 Owen Sound, ON Vacation Rentals

Recently Booked Vacation Rentals in Owen Sound