26+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  2. New Hampshire
  3. Keene
  4. West Chesterfield

West Chesterfield pickleball Stays, Resort Rentals, & Homes

About West Chesterfield Vacation Rentals

Discover over 26 amazing vacation rental options in West Chesterfield 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 West Chesterfield.

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 267.69 ft², with prices averaging US $161 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 West Chesterfield.

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Top Pickleball-Ready Accommodation Types in West Chesterfield

Type Count
Holiday Apartments 2
Vacation Homes 2

Use these Quick Filters to Find a Vacation Rental in West Chesterfield

★ 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 West Chesterfield with PickleTrip™.

Weather in West Chesterfield, NH

View the weather forecast for West Chesterfield before booking your West Chesterfield 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 West Chesterfield, NH

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


Madame Sherri Forest
Madame Sherris Castle Ruins
Wantastiquet Mountain
Actors Theatre Playhouse
United States Navy Seabee Bridge
Mount Snow
Keene State College
Bellows Falls Opera House
Spofford Lake
Greenfield Community College
Northfield Mount Hermon School
Brattleboro Bowl
Turner Falls
Landmark College
Asbury United Methodist Church
The Putney School
Monadnock State Park
Brattleboro Outlet Center
Brattleboro Farmers' Market
Granite Gorge

Other Places to Stay in West Chesterfield, NH


United States Navy Seabee Bridge 59 Properties
Wantastiquet Mountain 58 Properties
Madame Sherri Forest 55 Properties
Madame Sherris Castle Ruins 55 Properties
Actors Theatre Playhouse 42 Properties

Frequently Asked Questions About West Chesterfield?

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

How many PickleTrip vacation rentals or resorts are available in West Chesterfield?

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 26 properties listed in West Chesterfield 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 26 West Chesterfield, NH Vacation Rentals

Recently Booked Vacation Rentals in West Chesterfield