180+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Middlesex pickleball Stays, Resort Rentals, & Homes

About Middlesex Vacation Rentals

Discover over 180 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 1457.68 ft², with prices averaging US $538 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 98
Cottages 24
Holiday Apartments 3

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™.

Weather in Middlesex, NY

View the weather forecast for Middlesex before booking your Middlesex Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Middlesex, NY

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


Clarks Gully
Hill Cumorah Visitors Center
Keuka Lake
CMAC Performing Arts Center
Bristol Mountain Ski Resort
Finger Lakes Gaming and Racetrack
CaNonedaigua Lake
Hobart and William Smith Colleges
Three Brothers Wineries and Estates
Keuka College
Conesus Lake
Seneca Lake State Park
Honeoye Lake
Keuka Lake State Park
Ventosa Vineyards
Hunt Hollow
Sampson State Park
Ontario County Park at Gannett Hill
Finger Lakes Wine Center
Rose Hill Mansion

Other Places to Stay in Middlesex, NY


Clarks Gully 31 Properties

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!

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

Discover 2 accommodations with private or nearby pickleball courts in Middlesex. Some of the best destinations to stay and play pickleball are:

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 180 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 180 Middlesex, NY Vacation Rentals

Recently Booked Vacation Rentals in Middlesex