62+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. Canada
  2. Prince Edward Island
  3. Charlottetown
  4. Winsloe

Winsloe pickleball Stays, Resort Rentals, & Homes

About Winsloe Vacation Rentals

Discover over 62 amazing vacation rental options in Winsloe 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 Winsloe.

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 658.07 ft², with prices averaging US $223 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 Winsloe.

Show more
Show less

Top Pickleball-Ready Accommodation Types in Winsloe

Type Count
Vacation Homes 25
Holiday Apartments 12
Villas 2

Use these Quick Filters to Find a Vacation Rental in Winsloe

★ 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 Winsloe with PickleTrip™.

Weather in Winsloe, PE

View the weather forecast for Winsloe before booking your Winsloe 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

Frequently Asked Questions About Winsloe?

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

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

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

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 62 properties listed in Winsloe 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 62 Winsloe, PE Vacation Rentals

Recently Booked Vacation Rentals in Winsloe