315+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. Canada
  2. Ontario
  3. Barrie - Orillia
  4. Collingwood

Collingwood pickleball Stays, Resort Rentals, & Homes

About Collingwood Vacation Rentals

Discover over 315 amazing vacation rental options in Collingwood 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 Collingwood.

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 577.17 ft², with prices averaging $236 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 Collingwood.

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Top Pickleball-Ready Accommodation Types in Collingwood

Type Count
Vacation Homes 145
Holiday Apartments 39
Cottages 8
Villas 5

Use these Quick Filters to Find a Vacation Rental in Collingwood

★ 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 Collingwood with PickleTrip™.

Weather in Collingwood, ON

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

December - February
High 43°F       Low 21°F
March - May
High 64°F       Low 26°F
June - August
High 79°F       Low 59°F
September - November
High 75°F       Low 32°F

Top Attractions Around Collingwood, ON

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


Cranberry Resort Golf Course
Sunset Point Park
Collingwood Harbour
Blue Mountain Golf and Country Club
Collingwood Golf Course
St. Mary's Roman Catholic Church
Collingwood Eddie Bush Memorial Arena
Theatre Collingwood
Atoka Golf Course
Collingwood Museum
Eddie Bush Memorial Arena
White's Bay
Blue Mountain Ski Resort
Blue Mountain Village
Scandinave Spa Blue Mountain
Snow Valley Ski Resort
Collingwood Scenic Caves
Wasaga Beach Provincial Park
Blue Mountain Beach
Village at Blue

Other Places to Stay in Collingwood, ON


Blue Mountain Golf and Country Club 705 Properties
Cranberry Resort Golf Course 676 Properties
Collingwood Golf Course 623 Properties
Atoka Golf Course 463 Properties
White's Bay 408 Properties
Collingwood Harbour 300 Properties
Eddie Bush Memorial Arena 278 Properties
Collingwood Eddie Bush Memorial Arena 278 Properties
Theatre Collingwood 277 Properties
St. Mary's Roman Catholic Church 277 Properties
Collingwood Museum 273 Properties
Sunset Point Park 262 Properties

Frequently Asked Questions About Collingwood?

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

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

Discover 10 accommodations with private or nearby pickleball courts in Collingwood. Some of the best destinations to stay and play pickleball are:

Which vacation rentals, resorts, or hotels in Collingwood 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 Collingwood?

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 315 properties listed in Collingwood 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.


People Also Ask

There are 315 Collingwood, ON Vacation Rentals

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