Windsor pickleball Stays, Resort Rentals, & Homes
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Luxury Places to Stay in Windsor
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Top-Rated Villas with a Pool in Windsor
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Pet-Friendly Villas in Windsor
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Large Private Villas in Windsor
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Wheelchair Accessible Holiday Homes in Windsor
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Windsor Villas, Airbnb and Holiday Homes Under $200
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Instantly Bookable Villa Rentals in Windsor
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Book a Last Minute Place to Stay in Windsor
About Windsor Vacation Rentals
Discover over 49 amazing vacation rental options in Windsor 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 Windsor.
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 2425.13 ft², with prices averaging US $268 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 Windsor.
Top Pickleball-Ready Accommodation Types in Windsor
| Type | Count |
|---|---|
| Holiday Apartments | 8 |
| Vacation Homes | 8 |
| Cottages | 1 |
Use these Quick Filters to Find a Vacation Rental in Windsor
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★ 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 Windsor with PickleTrip™.
Weather in Windsor, QC
View the weather forecast for Windsor before booking your Windsor Vacation Rentals to confirm your best time to go.
Top Attractions Around Windsor, QC
PickleTrip offers a large selection of top attractions around Windsor . Research things to do on your vacation before you visit Windsor.
Frequently Asked Questions About Windsor?
What are the top vacation rentals, resorts, and hotels in Windsor 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 Windsor. 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 Windsor!
- P'tit St-François
- Le Havre Gris, a spacious private room for relaxing or working
- Fully equipped apartment with 2 bedrooms in our century-old residence.
- Fully equipped apartment with 1 bedroom in our century-old residence.n
- OTL Gouverneur Sherbrooke
- Oasis
- Bethel peaceful countryside location 5 min from hospitals
- Le nid des hirondelles
- Ile De Garde B&B
- Rowing, Waterfront, Spa
Which vacation rentals, resorts, or hotels in Windsor is best for families looking for a pickleball-getaway?
Looking for a fun and active getaway with pickleball courts in Windsor? 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 Windsor?
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 49 properties listed in Windsor 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.
