162+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  3. Pittsfield

Pittsfield pickleball Stays, Resort Rentals, & Homes

About Pittsfield Vacation Rentals

Discover over 162 amazing vacation rental options in Pittsfield 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 Pittsfield.

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 1182.36 ft², with prices averaging US $386 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 Pittsfield.

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Top Pickleball-Ready Accommodation Types in Pittsfield

Type Count
Vacation Homes 93
Holiday Apartments 9
Cottages 7
Villas 1

Use these Quick Filters to Find a Vacation Rental in Pittsfield

★ 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 Pittsfield with PickleTrip™.

Weather in Pittsfield, NY

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

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


National Baseball Hall of Fame
Cooperstown All Star Village Fields
Cooperstown Dreams Park
Colgate University
State University of New York-Oneonta
Otsego Lake
Brewery Ommegang
Hartwick College
Interskate 88
Farmers' Museum
Clark Sports Center
Doubleday Field
Foothills Performing Arts Center
Cooperstown Brewing Company
Wolf Mountain Nature Center
Blue Stone Golf Club
Fenimore Art Museum
Cooperstown Fun Park
Northeast Classic Car Museum
Joseph L. Popp

Other Places to Stay in Pittsfield, NY


Hoboken 103 Properties

Frequently Asked Questions About Pittsfield?

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

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

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

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 162 properties listed in Pittsfield 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 162 Pittsfield, NY Vacation Rentals

Recently Booked Vacation Rentals in Pittsfield