69+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Wainscott pickleball Stays, Resort Rentals, & Homes

About Wainscott Vacation Rentals

Discover over 69 amazing vacation rental options in Wainscott 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 Wainscott.

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 1232.79 ft², with prices averaging US $2,099 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 Wainscott.

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Top Pickleball-Ready Accommodation Types in Wainscott

Type Count
Vacation Homes 61
Cottages 2
Villas 1

Use these Quick Filters to Find a Vacation Rental in Wainscott

★ 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 Wainscott with PickleTrip™.

Weather in Wainscott, NY

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

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


Cooper's Beach
East Hampton Main Beach
Wolffer Estates Vineyard
Meschutt Beach
Guild Hall
Ditch Plains Beach
Hither Hills State Park
The Hamptons Beaches
Orient Beach State Park
Bay Street Theatre
Indian Wells Beach
Ponquogue Beach
Kontokosta Winery
Montauk Marine Basin
Harbes Family Farm
South Edison Beach
Halsey House
Old Hook Mill
Camp Hero State Park
Clovis Point

Other Places to Stay in Wainscott, NY


Hamptons 3,316 Properties
Wainscott Woods 448 Properties

Frequently Asked Questions About Wainscott?

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

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

Discover 12 accommodations with private or nearby pickleball courts in Wainscott. Some of the best destinations to stay and play pickleball are:

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

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

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 69 properties listed in Wainscott 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 69 Wainscott, NY Vacation Rentals

Recently Booked Vacation Rentals in Wainscott