190+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  2. Vermont
  3. Westfield

Westfield pickleball Stays, Resort Rentals, & Homes

About Westfield Vacation Rentals

Discover over 190 amazing vacation rental options in Westfield 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 Westfield.

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 1130.02 ft², with prices averaging US $520 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 Westfield.

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Top Pickleball-Ready Accommodation Types in Westfield

Type Count
Vacation Homes 72
Holiday Apartments 17
Cottages 6

Use these Quick Filters to Find a Vacation Rental in Westfield

★ 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 Westfield with PickleTrip™.

Weather in Westfield, VT

View the weather forecast for Westfield before booking your Westfield 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 Westfield, VT

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


Jay Peak Ski Resort
Pump House Indoor Waterpark
Lake Willoughby
Jay Peak
Jay Peak Pump House
Green Mountains
Jay Peak Resort Golf Course
Hill Farmstead Brewery
Lake Carmi
Haskell Free Library and Opera House
MAC Center for the Arts
The Governor's House
Orleans Country Club
Crystal Lake State Park
Newport Bike Path
Lake Salem Beach House
Lake Parker
Old Stone House Museum
Lake Memphremagog

Frequently Asked Questions About Westfield?

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

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

Discover 1 accommodations with private or nearby pickleball courts in Westfield. Some of the best destinations to stay and play pickleball are:

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

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

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 190 properties listed in Westfield 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.


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There are 190 Westfield, VT Vacation Rentals

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