Connecticut pickleball Stays, Resort Rentals, & Homes
About Connecticut Vacation Rentals
Discover over 6681 amazing vacation rental options in Connecticut 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 Connecticut.
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 861.15 ft², with prices averaging US $426 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 Connecticut.
Top Pickleball-Ready Accommodation Types in Connecticut
| Type | Count |
|---|---|
| Vacation Homes | 3367 |
| Holiday Apartments | 1726 |
| Cottages | 477 |
| Villas | 72 |
Use these Quick Filters to Find a Vacation Rental in Connecticut
★ 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 Connecticut with PickleTrip™.
Weather in Connecticut, US
View the weather forecast for Connecticut before booking your Connecticut Vacation Rentals to confirm your best time to go.
Top Attractions Around Connecticut, US
PickleTrip offers a large selection of top attractions around Connecticut . Research things to do on your vacation before you visit Connecticut.
Other Places to Stay in Connecticut, US
Frequently Asked Questions About Connecticut?
What are the top vacation rentals, resorts, and hotels in Connecticut 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 Connecticut. 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 Connecticut!
- Summer Beach Fun in a Exclusive beach community!
- Now available for short term rentals during the off season.
- The beach is waiting.
- Summer 2026 Available! 4BR/3BA Woodridge Lake Tennis Pool WiFi AC
- Lake Fun: PingPong, Pool Table, Slide, EV Charger
- Candlewood Lake Perfection: Large and very private House, property and pool.
- Point O Woods House walk to private beach
- Coastal Black Point Beach House
- Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access
- Charming Seaside Cottage 2-bedroom with WiFi, AC in Lord's Point ,Stonington.
How many pickleball-ready properties have private pools in Connecticut?
Discover 391 accommodations with private or nearby pickleball courts in Connecticut. Some of the best destinations to stay and play pickleball are:
- Private Kent Getaway With Views, Pond & Pool
- Family Friendly Apt with Gym
- Las Flores Villa
- Breathtaking home with unforgettable views
Which vacation rentals, resorts, or hotels in Connecticut is best for families looking for a pickleball-getaway?
Looking for a fun and active getaway with pickleball courts in Connecticut? 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.
- Point O Woods House walk to private beach
- Waterfront Home on Bantam Lake with Private Beach
- The Homestead
How many PickleTrip vacation rentals or resorts are available in Connecticut?
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 6681 properties listed in Connecticut 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.
