31+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  3. Westport

Westport pickleball Stays, Resort Rentals, & Homes

About Westport Vacation Rentals

Discover over 31 amazing vacation rental options in Westport 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 Westport.

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 877.2 ft², with prices averaging US $450 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 Westport.

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Top Pickleball-Ready Accommodation Types in Westport

Type Count
Vacation Homes 20
Holiday Apartments 2
Cottages 2

Use these Quick Filters to Find a Vacation Rental in Westport

★ 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 Westport with PickleTrip™.

Weather in Westport, MA

View the weather forecast for Westport before booking your Westport 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 Westport, MA

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


Lizzie Borden Bed & Breakfast
Horseneck State Beach
Handy House
Westport Town Farm
Westport Rivers Vineyard & Winery
Acoaxet Golf Club
Dedee Shattuck Gallery
Acoaxet Club
Buzzards Bay Brewing
Battleship Cove
Marine Museum
Brown University
Dunkin' Donuts Center
The Breakers
Newport Mansions
Providence Place Mall
Providence Performing Arts Center
Rhode Island Convention Center
Easton's Beach

Other Places to Stay in Westport, MA


Dedee Shattuck Gallery 132 Properties
Acoaxet Club 122 Properties
Westport Rivers Vineyard & Winery 121 Properties
Westport Town Farm 116 Properties
Handy House 114 Properties
Acoaxet Golf Club 89 Properties
North Westport 76 Properties
Westport Harbor 73 Properties
Westport Point 58 Properties
Horseneck State Beach 39 Properties
Lizzie Borden Bed & Breakfast 26 Properties
Marine Museum 26 Properties

Frequently Asked Questions About Westport?

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

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

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

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 31 properties listed in Westport 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
Westport Harbor Vacation Rentals in Westport, Massachusetts 73

People Also Ask

There are 31 Westport, MA Vacation Rentals

Recently Booked Vacation Rentals in Westport