198+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. New Hampshire
  3. Cheshire County

Cheshire County pickleball Stays, Resort Rentals, & Homes

About Cheshire County Vacation Rentals

Discover over 198 amazing vacation rental options in Cheshire County 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 Cheshire County.

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 1117.61 ft², with prices averaging US $363 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 Cheshire County.

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Top Pickleball-Ready Accommodation Types in Cheshire County

Type Count
Vacation Homes 92
Cottages 24
Holiday Apartments 16
Villas 2

Use these Quick Filters to Find a Vacation Rental in Cheshire County

★ 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 Cheshire County with PickleTrip™.

Weather in Cheshire County, NH

View the weather forecast for Cheshire County before booking your Cheshire County 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 Cheshire County, NH

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


Keene State College
Spofford Lake
Asbury United Methodist Church
Monadnock State Park
Granite Gorge
Colonial Theatre
Madame Sherri Forest
Brentwood Golf Course
Madame Sherris Castle Ruins
Central Square
Cathedral of the Pines
Pete's Stand Vegetables
Rhododendron State Park
Chesterfield Gorge Natural Area
Jaffrey Civic Center
Stonewall Farm
Historical Society of Cheshire County
Cheshire Children's Museum
Unbridled Chocolates
Walpole Farmers Market
Walpole Artisans Cooperative
Alumni Field
Friendly Farm
The Fells
Wantastiquet Mountain
CC&H Framing / Pepper Pete's Hot Shop
Hooper Golf Club
Actors Theatre Playhouse
Pitcher Mountain
Walpole Artisans Cooperative

Other Places to Stay in Cheshire County, NH


Monadnock Region 249 Properties
Keene 185 Properties
Fitzwilliam 92 Properties
Swanzey 53 Properties
Historic Main Street 50 Properties
West Chesterfield 45 Properties
Stoddard 44 Properties
Harrisville 42 Properties
Dublin 42 Properties
Jaffrey 38 Properties
Rindge 32 Properties
Walpole 31 Properties

Frequently Asked Questions About Cheshire County?

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

How many pickleball-ready properties have private pools in Cheshire County?

Discover 2 accommodations with private or nearby pickleball courts in Cheshire County. Some of the best destinations to stay and play pickleball are:

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

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

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 198 properties listed in Cheshire County 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 198 Cheshire County, NH Vacation Rentals

Recently Booked Vacation Rentals in Cheshire County