2099+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Vermont
  3. Windsor County

Windsor County pickleball Stays, Resort Rentals, & Homes

About Windsor County Vacation Rentals

Discover over 2099 amazing vacation rental options in Windsor 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 Windsor 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 1119.26 ft², with prices averaging US $565 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 Windsor County.

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Top Pickleball-Ready Accommodation Types in Windsor County

Type Count
Vacation Homes 1053
Holiday Apartments 188
Cottages 40
Villas 6

Use these Quick Filters to Find a Vacation Rental in Windsor 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 Windsor County with PickleTrip™.

Weather in Windsor County, VT

View the weather forecast for Windsor County before booking your Windsor 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 Windsor County, VT

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


Okemo Mountain Resort
Quechee Gorge
Jackson Gore Ski Resort at Okemo
King Arthur Flour
Quechee Gorge Village
Little Pico Mountain
Weston Playhouse
Suicide Six Ski Area
Weston Priory
Mt Ascutney State Park
Upper Valley Aquatic Center
Sugarbush Farm
Simon Pearce Mill
Mount Ascutney
Woodstock Country Club
Billings Farm and Museum
Okemo Valley Golf Club
Silver Lake State Park
Vermont River Tubing
Woodstock Town Hall Theatre
Briggs Opera House
Montshire Museum of Science
Wilderness Trails
Buttermilk Falls
Long Trail Brewing Company
Calvin Coolidge Historic Site
Mount Tom Peak
Vermont Institiute of Natural Science
Calvin Coolidge Homestead
Harpoon Brewery

Other Places to Stay in Windsor County, VT


Ludlow 706 Properties
Bridgewater Corners 119 Properties
West Bridgewater 89 Properties
Cavendish 82 Properties
Woodstock 70 Properties
Quechee 62 Properties
Plymouth 60 Properties
Chester 58 Properties
Chester Depot 58 Properties
Proctorsville 44 Properties
Weston 35 Properties
West Windsor 28 Properties

Frequently Asked Questions About Windsor County?

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

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

Discover 66 accommodations with private or nearby pickleball courts in Windsor County. Some of the best destinations to stay and play pickleball are:

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

Looking for a fun and active getaway with pickleball courts in Windsor 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 Windsor 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 2099 properties listed in Windsor County 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.


People Also Ask

There are 2099 Windsor County, VT Vacation Rentals

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