75+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Connecticut
  3. New Haven
  4. Derby

Derby pickleball Stays, Resort Rentals, & Homes

About Derby Vacation Rentals

Discover over 75 amazing vacation rental options in Derby 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 Derby.

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 343.56 ft², with prices averaging US $245 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 Derby.

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Top Pickleball-Ready Accommodation Types in Derby

Type Count
Vacation Homes 29
Holiday Apartments 22
Cottages 4

Use these Quick Filters to Find a Vacation Rental in Derby

★ 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 Derby with PickleTrip™.

Weather in Derby, CT

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

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


Osborndale State Park
Osborne Homestead Museum
Yale University
Yale-New Haven Hospital
Toyota Presents Oakdale Theatre
Quinnipiac University
Fairfield University
Shubert Theater
Palace Theatre
Danbury Fair Mall
Sacred Heart University
Webster Bank Arena
New Haven Green
University of New Haven
Choate Rosemary Hall
CoCo Key Water Resort Hotel & Convention Center - Waterbury
New Haven City Hall
Southern Connecticut State University
Quassy Amusement Park
Candlewood Lake

Other Places to Stay in Derby, CT


Osborne Homestead Museum 70 Properties
Osborndale State Park 62 Properties

Frequently Asked Questions About Derby?

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

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

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

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 75 properties listed in Derby 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 75 Derby, CT Vacation Rentals

Recently Booked Vacation Rentals in Derby