290+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  3. Westerly

Westerly pickleball Stays, Resort Rentals, & Homes

About Westerly Vacation Rentals

Discover over 290 amazing vacation rental options in Westerly 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 Westerly.

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 759.16 ft², with prices averaging $641 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 Westerly.

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Top Pickleball-Ready Accommodation Types in Westerly

Type Count
Vacation Homes 170
Holiday Apartments 30
Cottages 28
Villas 3

Use these Quick Filters to Find a Vacation Rental in Westerly

★ 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 Westerly with PickleTrip™.

Weather in Westerly, RI

View the weather forecast for Westerly before booking your Westerly 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 Westerly, RI

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


Misquamicut State Beach
The Flying Horse Carousel
Water Wizz of Westerly
Weekapaug Golf Club
Westerly Public Library
Wilcox Park
Atlantic Beach Park
East Beach Watch Hill
Granite Theatre
Ninigret
Flying Horses Carousel
Black Duck Gallery
Babcock-Smith House
Westerly Hospital
Foxwoods Resort Casino
Mohegan Sun Casino
Mystic Seaport
Mohegan Sun Arena
Foxwoods Resort & Casino
Mystic Aquarium and Institute for Exploration

Other Places to Stay in Westerly, RI


Weekapaug Golf Club 221 Properties
Atlantic Beach Park 221 Properties
Water Wizz of Westerly 221 Properties
East Beach 217 Properties
Misquamicut State Beach 214 Properties
Westerly Hospital 212 Properties
Weekapaug 205 Properties
Flying Horses Carousel 157 Properties
Watch Hill Historic District 149 Properties
Haversham 129 Properties
Watch Hill 106 Properties
Misquamicut 69 Properties

Frequently Asked Questions About Westerly?

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

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

Discover 9 accommodations with private or nearby pickleball courts in Westerly. Some of the best destinations to stay and play pickleball are:

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

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

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 290 properties listed in Westerly 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.

Nearby Neighborhood (1) 
Neighborhood Property Count
Watch Hill Historic District Vacation Rentals in Westerly, Rhode Island 149

People Also Ask

There are 290 Westerly, RI Vacation Rentals

Recently Booked Vacation Rentals in Westerly