Old Windsor pickleball Stays, Resort Rentals, & Homes

Frequently Asked Questions About Old Windsor?

What are the top vacation rentals, resorts, and hotels in Old 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 Old 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 Old Windsor!

• Gorgeous Country Cottage, beside Windsor Great Park & overlooking Windsor Castle
• Detached Luxury Gatehouse in rural surroundings on a small country estate
• Charming 3BR Victorian Cottage in the historic town of Colnbrook, Berkshire
• A magical and romantic getaway near Windsor Castle and beside Windsor Great Park
• Thames riverside location with direct Windsor Castle views, re-open now!
• Courtyard Apartment near Windsor, and the Great Park
• River guest house with jacuzzi, fire and boat hire
• Luxury Family Home in Central Windsor with Large Garden, Games Room, Office, Parking & Pet-Friendly
• Immaculate Central Windsor Town House
• Radiant Penthouse on the Banks of the Thames

How many pickleball-ready properties have private pools in Old Windsor?

Discover 4 accommodations with private or nearby pickleball courts in Old Windsor. Some of the best destinations to stay and play pickleball are:

• Riverside Retreat with Private Sauna
• Romantic 3Beds Yacht Escape on Thames
• De Vere Beaumont Estate
• Hilton London Heathrow Airport Terminal 5

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

Looking for a fun and active getaway with pickleball courts in Old 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.

• In the heart of Windsor, a spacious and light 2bed, 2bath, very near the Castle
• Consorts & Concubines, Opposite Windsor Castle, Castle view, Center of town, 4 Bed Apartment, Sleeps up to 7, Consorts & Concubines
• Immaculate Central Windsor Town House

How many PickleTrip vacation rentals or resorts are available in Old 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 931 properties listed in Old 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.

Nearby Neighborhood (1)