146+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. New York
  3. Shelter Island

Shelter Island pickleball Stays, Resort Rentals, & Homes

About Shelter Island Vacation Rentals

Discover over 146 amazing vacation rental options in Shelter Island 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 Shelter Island.

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 909.39 ft², with prices averaging US $1,042 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 Shelter Island.

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Top Pickleball-Ready Accommodation Types in Shelter Island

Type Count
Vacation Homes 117
Holiday Apartments 4
Cottages 3

Use these Quick Filters to Find a Vacation Rental in Shelter Island

★ 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 Shelter Island with PickleTrip™.

Weather in Shelter Island, NY

View the weather forecast for Shelter Island before booking your Shelter Island 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 Shelter Island, NY

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


Mashomack Preserve
Shelter Island Kayak
Wades Beach
Sylvester Manor
Havens House
Shelter Island Historical Society
Cooper's Beach
East Hampton Main Beach
Wolffer Estates Vineyard
Hammonasset Beach State Park
Meschutt Beach
Guild Hall
Ditch Plains Beach
Hither Hills State Park
Clinton Crossing Premium Outlets
The Hamptons Beaches
Orient Beach State Park
Bay Street Theatre
Indian Wells Beach
Ponquogue Beach

Other Places to Stay in Shelter Island, NY


Sylvester Manor 363 Properties
Shelter Island Kayak 305 Properties
Shelter Island Historical Society 222 Properties
Havens House 219 Properties
Menantic Creek 213 Properties
Shorewood 182 Properties
Wades Beach 178 Properties
Mashomack Preserve 174 Properties
Shelter Island Heights 112 Properties

Frequently Asked Questions About Shelter Island?

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

How many pickleball-ready properties have private pools in Shelter Island?

Discover 22 accommodations with private or nearby pickleball courts in Shelter Island. Some of the best destinations to stay and play pickleball are:

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

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

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 146 properties listed in Shelter Island 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.

Nearby Neighborhood (5) 
Neighborhood Property Count
The Heights Vacation Rentals in Shelter Island, New York 419
Coecles Harbor Vacation Rentals in Shelter Island, New York 293
Menantic Creek Vacation Rentals in Shelter Island, New York 213
Shorewood Vacation Rentals in Shelter Island, New York 182
Montclair Colony Vacation Rentals in Shelter Island, New York 197

People Also Ask

There are 146 Shelter Island, NY Vacation Rentals

Recently Booked Vacation Rentals in Shelter Island