598+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Orleans pickleball Stays, Resort Rentals, & Homes

About Orleans Vacation Rentals

Discover over 598 amazing vacation rental options in Orleans 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 Orleans.

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 1393.88 ft², with prices averaging US $758 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 Orleans.

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Top Pickleball-Ready Accommodation Types in Orleans

Type Count
Vacation Homes 542
Cottages 24
Holiday Apartments 11

Use these Quick Filters to Find a Vacation Rental in Orleans

★ 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 Orleans with PickleTrip™.

Weather in Orleans, MA

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

December - February
High 42°F       Low 21°F
March - May
High 64°F       Low 23°F
June - August
High 80°F       Low 58°F
September - November
High 75°F       Low 32°F

Top Attractions Around Orleans, MA

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


Nauset Beach
Skaket Beach
Orleans Bowling Center
Cape Escape Adventure Golf
Church of the Transfiguration Orleans
Academy Playhouse
Orleans Historical Society Meeting House Museum
Academy of Performing Arts
Addison Art Gallery
Nauset Inlet
Rock Harbor Beach
Jonathan Young Windmill
French Cable Station Museum
Cape Codder Water Park
Harwich Port
Hyannis Harbor
Cape Cod National Seashore
Mayflower Beach
West Dennis Beach
Seagull Beach

Other Places to Stay in Orleans, MA


Orleans Bowling Center 910 Properties
Cape Escape Adventure Golf 887 Properties
Academy of Performing Arts 877 Properties
Jonathan Young Windmill 864 Properties
Addison Art Gallery 855 Properties
French Cable Station Museum 855 Properties
Academy Playhouse 819 Properties
Orleans Historical Society Meeting House Museum 809 Properties
Church of the Transfiguration Orleans 798 Properties
Rock Harbor Beach 786 Properties
East Orleans 193 Properties
South Orleans 39 Properties

Frequently Asked Questions About Orleans?

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

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

Discover 40 accommodations with private or nearby pickleball courts in Orleans. Some of the best destinations to stay and play pickleball are:

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

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

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 598 properties listed in Orleans 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 598 Orleans, MA Vacation Rentals

Recently Booked Vacation Rentals in Orleans