188+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Highland pickleball Stays, Resort Rentals, & Homes

About Highland Vacation Rentals

Discover over 188 amazing vacation rental options in Highland 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 Highland.

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 395.46 ft², with prices averaging $145 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 Highland.

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Top Pickleball-Ready Accommodation Types in Highland

Type Count
Holiday Apartments 66
Vacation Homes 66
Villas 1

Use these Quick Filters to Find a Vacation Rental in Highland

★ 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 Highland with PickleTrip™.

Weather in Highland, ON

View the weather forecast for Highland before booking your Highland 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

Other Places to Stay in Highland, ON


Earl Nichols Arena 159 Properties

Frequently Asked Questions About Highland?

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

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

Discover 7 accommodations with private or nearby pickleball courts in Highland. Some of the best destinations to stay and play pickleball are:

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

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 188 properties listed in Highland 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 (3) 
Neighborhood Property Count
Westminster Vacation Rentals in London, Ontario 40
South London Vacation Rentals in London, Ontario 31
White Oaks Vacation Rentals in London, Ontario 125

People Also Ask

There are 188 Highland, ON Vacation Rentals

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