87+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  2. Connecticut
  3. Old Saybrook
  4. Madison

Madison pickleball Stays, Resort Rentals, & Homes

About Madison Vacation Rentals

Discover over 87 amazing vacation rental options in Madison 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 Madison.

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 1004.28 ft², with prices averaging US $573 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 Madison.

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Top Pickleball-Ready Accommodation Types in Madison

Type Count
Vacation Homes 62
Cottages 14
Holiday Apartments 4

Use these Quick Filters to Find a Vacation Rental in Madison

★ 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 Madison with PickleTrip™.

Weather in Madison, CT

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

December - February
High 42°F       Low 22°F
March - May
High 65°F       Low 23°F
June - August
High 79°F       Low 58°F
September - November
High 75°F       Low 32°F

Top Attractions Around Madison, CT

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


Hammonasset Beach State Park
Anna Mia's
Meigs Point Nature Center
North Madison Shopping Center
Hammonasset Beach
Deacon John Grave House
RJ Julia Booksellers
Scranton Memorial Library
Allis-Bushnell House and Museum
Yale University
Yale-New Haven Hospital
Toyota Presents Oakdale Theatre
Quinnipiac University
Wesleyan University
Shubert Theater
Essex Steam Train
New Haven Green
University of New Haven
Choate Rosemary Hall
CoCo Key Water Resort Hotel & Convention Center - Waterbury

Other Places to Stay in Madison, CT


Hammonasset Beach State Park 114 Properties
Hammonasset Beach 106 Properties
Meigs Point Nature Center 101 Properties
Madison Center 85 Properties
Deacon John Grave House 85 Properties
North Madison Shopping Center 82 Properties
Anna Mia's 79 Properties
RJ Julia Booksellers 79 Properties
Scranton Memorial Library 78 Properties
Allis-Bushnell House and Museum 76 Properties

Frequently Asked Questions About Madison?

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

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

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

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 87 properties listed in Madison 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.

Nearby Neighborhood (1) 
Neighborhood Property Count
Madison Center Vacation Rentals in Old Saybrook, Connecticut 85

People Also Ask

There are 87 Madison, CT Vacation Rentals

Recently Booked Vacation Rentals in Madison