77+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  2. Connecticut
  3. Hartford
  4. Simsbury

Simsbury pickleball Stays, Resort Rentals, & Homes

About Simsbury Vacation Rentals

Discover over 77 amazing vacation rental options in Simsbury 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 Simsbury.

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 564.88 ft², with prices averaging US $387 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 Simsbury.

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Top Pickleball-Ready Accommodation Types in Simsbury

Type Count
Vacation Homes 44
Holiday Apartments 18
Cottages 1
Villas 1

Use these Quick Filters to Find a Vacation Rental in Simsbury

★ 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 Simsbury with PickleTrip™.

Weather in Simsbury, CT

View the weather forecast for Simsbury before booking your Simsbury 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 Simsbury, CT

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


Rosedale Farms & Vineyards
Performing Arts Center at Simsbury Meadows
Phelps Tavern Museum
Talcott Mountain State Park
XL Center
Six Flags New England
Xfinity Theatre
University of Hartford
Naismith Memorial Basketball Hall of Fame
Connecticut Convention Center
MassMutual Center
Trinity College
Eastern States Exposition
MGM Springfield
Lake Compounce
Big E
Springfield Armory
Holyoke Mall
Connecticut Science Center

Other Places to Stay in Simsbury, CT


Rosedale Farms & Vineyards 71 Properties
Phelps Tavern Museum 64 Properties
Simsbury Center 62 Properties
Performing Arts Center at Simsbury Meadows 62 Properties
Talcott Mountain State Park 36 Properties

Frequently Asked Questions About Simsbury?

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

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

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

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

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

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 77 properties listed in Simsbury 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
Simsbury Center Vacation Rentals in Hartford, Connecticut 62

People Also Ask

There are 77 Simsbury, CT Vacation Rentals

Recently Booked Vacation Rentals in Simsbury