Middlesex County pickleball Stays, Resort Rentals, & Homes

Frequently Asked Questions About Middlesex County?

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

• Tradewinds on the Sea, Oceanfront, See Tryall Club Summer/FallPromotion Below
• Luxury 13-bedroom, 7-acre, oceanfront villa, with all-inclusive option.
• Canoe Cove 7-Ultimate luxury, beachfront, fully staffed, tennis, kayaks,gym
• Mango Hill 5 Minutes walk to the beach! Staffed! Gated Communit!y! Pool
• Suite Dreamers Cottage
• Stunning villa in Jamaica - Buttonwood Reef
• Luxurious 7 Bedroom Beachfront Villa in Old Fort Bay, St. Ann
• Scotch on the Rocks -WATERFRONT! CHEF! STAFF! FAMILY FRIENDLY! POOL! KAYAKS!
• Villa Janus, Round Hill, Fully Staffed with Chef and Butlers
• Malatai - A Stunning Private Luxury Beachfront Villa

How many pickleball-ready properties have private pools in Middlesex County?

Discover 658 accommodations with private or nearby pickleball courts in Middlesex County. Some of the best destinations to stay and play pickleball are:

• Love & Livity at the Tryall Club by Personal Villas - A Relaxing Ambiance
• El Cielo
• 195 m² Villa ∙ 5 bedrooms ∙ 14 guests
• Palm BlossomJA Manor

Which vacation rentals, resorts, or hotels in Middlesex County 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.

• Love & Livity at the Tryall Club by Personal Villas - A Relaxing Ambiance
• 2 Love Birds Abode 3 Minutes to Beach
• 613 m² Resort ∙ 6 bedrooms ∙ 127 guests

How many PickleTrip vacation rentals or resorts are available in Middlesex County?

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 4274 properties listed in Middlesex County 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.

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