258+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  3. Riverhead

Riverhead pickleball Stays, Resort Rentals, & Homes

About Riverhead Vacation Rentals

Discover over 258 amazing vacation rental options in Riverhead 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 Riverhead.

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 792.08 ft², with prices averaging US $615 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 Riverhead.

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Top Pickleball-Ready Accommodation Types in Riverhead

Type Count
Vacation Homes 174
Cottages 37
Holiday Apartments 10
Villas 3

Use these Quick Filters to Find a Vacation Rental in Riverhead

★ 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 Riverhead with PickleTrip™.

Weather in Riverhead, NY

View the weather forecast for Riverhead before booking your Riverhead 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 Riverhead, NY

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


Tanger Outlet Center
Long Island Aquarium and Exhibition Center
Suffolk Theater
Roanoke Vineyards
Clovis Point
Martha Clara Vineyards
Safari Adventure
Indian Island County Park
Riverhead Raceway
Baiting Hollow Hummingbird Sanctuary
Long Island National Golf Club
Jamesport Vineyards
Sherwood House Vineyards - Jamesport Tasting House
All Star Bowling
Palmer Vineyards
Hallockville Museum Farm
Out East Family Fun
Paumanok Vineyards
South Jamesport Park

Other Places to Stay in Riverhead, NY


Suffolk County 4,541 Properties
Northampton 588 Properties
Clovis Point 174 Properties
South Jamesport Park 169 Properties
Martha Clara Vineyards 163 Properties
South Jamesport 162 Properties
Flanders 96 Properties
North Fork 95 Properties
Northville 79 Properties
Aquebogue 30 Properties
Jamesport 28 Properties
Baiting Hollow 27 Properties

Frequently Asked Questions About Riverhead?

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

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

Discover 27 accommodations with private or nearby pickleball courts in Riverhead. Some of the best destinations to stay and play pickleball are:

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

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

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 258 properties listed in Riverhead in 2026, 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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There are 258 Riverhead, NY Vacation Rentals

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