95+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. New York
  3. Old Chatham

Old Chatham pickleball Stays, Resort Rentals, & Homes

About Old Chatham Vacation Rentals

Discover over 95 amazing vacation rental options in Old Chatham 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 Old Chatham.

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 1355.45 ft², with prices averaging US $477 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 Old Chatham.

Show more
Show less

Top Pickleball-Ready Accommodation Types in Old Chatham

Type Count
Vacation Homes 62
Cottages 10
Holiday Apartments 9
Villas 1

Use these Quick Filters to Find a Vacation Rental in Old Chatham

★ 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 Old Chatham with PickleTrip™.

Weather in Old Chatham, NY

View the weather forecast for Old Chatham before booking your Old Chatham 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 Old Chatham, NY

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


Shaker Museum and Library
Times Union Center
Jiminy Peak Mountain Resort
Albany Medical Center
Palace Theater
Tanglewood Music Center
The Egg
Empire State Plaza Convention Center
Ski Butternut
Catamount Ski Area
Rensselaer Polytechnic Institute
Albany Capital Center
New York State Museum
Norman Rockwell Museum
National Shrine of the Divine Mercy
New York State Capitol Building
Lee Prime Outlets
Albany Medical College
Washington Park
Albany College of Pharmacy and Health Sciences

Other Places to Stay in Old Chatham, NY


Shaker Museum and Library 68 Properties

Frequently Asked Questions About Old Chatham?

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

How many pickleball-ready properties have private pools in Old Chatham?

Discover 3 accommodations with private or nearby pickleball courts in Old Chatham. Some of the best destinations to stay and play pickleball are:

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

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

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 95 properties listed in Old Chatham 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 95 Old Chatham, NY Vacation Rentals

Recently Booked Vacation Rentals in Old Chatham