506+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  2. Connecticut
  3. Middlesex County

Middlesex County pickleball Stays, Resort Rentals, & Homes

About Middlesex County Vacation Rentals

Discover over 506 amazing vacation rental options in Middlesex 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 Middlesex 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 913.97 ft², with prices averaging US $441 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 Middlesex County.

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Top Pickleball-Ready Accommodation Types in Middlesex County

Type Count
Vacation Homes 306
Cottages 90
Holiday Apartments 43

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

Weather in Middlesex County, CT

View the weather forecast for Middlesex County before booking your Middlesex 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 Middlesex County, CT

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


Wesleyan University
Essex Steam Train
Essex Library
Clinton Crossing Premium Outlets
Powder Ridge Mountain Park and Resort
Goodspeed Opera House
Kidcity Children's Museum
Wadsworth Mansion
Tanger Outlets
Harvey's Beach
Devil's Hopyard State Park
Lyman Orchards
Ivoryton Playhouse
Brownstone Exploration & Discovery Park
Essex Saybrook Antique Village Shopping Center
Gillette Castle State Park
Cockaponset State Forest
Katharine Hepburn Cultural Arts Center
Crystal Lake Town Park
Millers Pond State Park
Clinton Plaza Shopping Center
Museum of Fife and Drum
Smith Park
Banner Country Club
Fox Hopyard Golf Club
Stay and Play LLC
Machimoodus State Park
Essex Plaza Shopping Center
Amasa Day House
Essex Island Marina

Other Places to Stay in Middlesex County, CT


Old Saybrook 313 Properties
Westbrook Center 81 Properties
Westbrook 81 Properties
East Haddam 68 Properties
Clinton 60 Properties
Haddam 53 Properties
Killingworth 38 Properties
Middletown 32 Properties
Middlefield 32 Properties
Lake Pocotopaug 31 Properties
East Hampton 25 Properties
Saybrook Manor 24 Properties

Frequently Asked Questions About Middlesex County?

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

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

Discover 12 accommodations with private or nearby pickleball courts in Middlesex County. Some of the best destinations to stay and play pickleball are:

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

Looking for a fun and active getaway with pickleball courts in Middlesex 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 Middlesex 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 506 properties listed in Middlesex 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 506 Middlesex County, CT Vacation Rentals

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