150+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. Canada
  2. Ontario
  3. Owen Sound
  4. Grey Highlands

Grey Highlands pickleball Stays, Resort Rentals, & Homes

About Grey Highlands Vacation Rentals

Discover over 150 amazing vacation rental options in Grey Highlands 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 Grey Highlands.

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 731.16 ft², with prices averaging US $374 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 Grey Highlands.

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Top Pickleball-Ready Accommodation Types in Grey Highlands

Type Count
Vacation Homes 55
Cottages 36
Holiday Apartments 7

Use these Quick Filters to Find a Vacation Rental in Grey Highlands

★ 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 Grey Highlands with PickleTrip™.

Weather in Grey Highlands, ON

View the weather forecast for Grey Highlands before booking your Grey Highlands 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 Grey Highlands, ON

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


Beaver Valley Ski Club
Eugenia Falls Conservation Area
Eugenia Lake
South Grey Museum and Historical Library
Old Baldy Conservation Area
Hoggs Falls
Artsonten
Blue Mountain Ski Resort
Blue Mountain Village
Bruce Peninsula
Scandinave Spa Blue Mountain
Collingwood Scenic Caves
Wasaga Beach Provincial Park
Blue Mountain Beach
Village at Blue
Mono Cliffs Provincial Park
Earl Rowe Provincial Park
Inglis Falls
Cranberry Resort Golf Course
Sunset Point Park

Other Places to Stay in Grey Highlands, ON


Priceville 89 Properties
Flesherton 84 Properties
Old Baldy Conservation Area 76 Properties
Kimberley 65 Properties
South Grey Museum and Historical Library 62 Properties
Artsonten 60 Properties
Eugenia Lake 48 Properties
Eugenia Falls Conservation Area 43 Properties
Feversham 41 Properties
Beaver Valley Ski Club 33 Properties
Hoggs Falls 30 Properties
Markdale 24 Properties

Frequently Asked Questions About Grey Highlands?

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

How many pickleball-ready properties have private pools in Grey Highlands?

Discover 2 accommodations with private or nearby pickleball courts in Grey Highlands. Some of the best destinations to stay and play pickleball are:

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

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

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 150 properties listed in Grey Highlands 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 150 Grey Highlands, ON Vacation Rentals

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