56+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. Jamaica
  2. Hanover
  3. Montego Bay
  4. Middlesex

Middlesex pickleball Stays, Resort Rentals, & Homes

About Middlesex Vacation Rentals

Discover over 56 amazing vacation rental options in Middlesex 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 Middlesex.

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 410.42 ft², with prices averaging US $936 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 Middlesex.

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Top Pickleball-Ready Accommodation Types in Middlesex

Type Count
Vacation Homes 21
Villas 17
Holiday Apartments 12

Use these Quick Filters to Find a Vacation Rental in Middlesex

★ 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 Middlesex with PickleTrip™.

Top Attractions Around Middlesex, JM

PickleTrip offers a large selection of top attractions around Middlesex . Research things to do on your vacation before you visit Middlesex.


Seven Mile Beach
Hip Strip
Doctor's Cave Beach
Montego Bay Cruise Ship Terminal
Negril Cliffs
Montego Bay Marine Park
Bloody Bay Beach
Negril Lighthouse
Jamaica Beaches
Bloody Bay
Tryall Golf Club
AquaSol Theme Park
Dead End Beach
Kool Runnings Water Park
Rocklands Bird Sanctuary
Hedonism II
Half Moon Beach
Negril Hills Golf Club
Sam Sharpe Square
Cornwall Regional Hospital

Frequently Asked Questions About Middlesex?

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

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

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

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 56 properties listed in Middlesex 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 56 Middlesex, JM Vacation Rentals

Recently Booked Vacation Rentals in Middlesex