173+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Wilton pickleball Stays, Resort Rentals, & Homes

About Wilton Vacation Rentals

Discover over 173 amazing vacation rental options in Wilton 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 Wilton.

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 1089.02 ft², with prices averaging US $656 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 Wilton.

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Top Pickleball-Ready Accommodation Types in Wilton

Type Count
Vacation Homes 98
Holiday Apartments 27
Cottages 15
Villas 3

Use these Quick Filters to Find a Vacation Rental in Wilton

★ 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 Wilton with PickleTrip™.

Weather in Wilton, CT

View the weather forecast for Wilton before booking your Wilton 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 Wilton, CT

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


Wilton Historical Society
Weir Farm National Historic Site
Gateway Shopping Center
Silvermine Golf Club
Capitol Theatre
Fairfield University
Westchester County Center
Purchase College
Norwalk Maritime Aquarium
Rye Playland
Ridgefield Playhouse
Danbury Fair Mall
Sacred Heart University
Webster Bank Arena
The Westchester Mall
Sunken Meadow State Park
Historic South Norwalk
Thunder Ridge Ski Resort
Manhattanville College
Chelsea Piers

Other Places to Stay in Wilton, CT


Gateway Shopping Center 82 Properties
Silvermine Golf Club 53 Properties
Wilton Historical Society 30 Properties
Weir Farm National Historic Site 24 Properties

Frequently Asked Questions About Wilton?

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

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

Discover 17 accommodations with private or nearby pickleball courts in Wilton. Some of the best destinations to stay and play pickleball are:

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

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

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 173 properties listed in Wilton 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.


People Also Ask

There are 173 Wilton, CT Vacation Rentals

Recently Booked Vacation Rentals in Wilton