485+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  3. Old Saybrook

Old Saybrook pickleball Stays, Resort Rentals, & Homes

About Old Saybrook Vacation Rentals

Discover over 485 amazing vacation rental options in Old Saybrook 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 Old Saybrook.

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 904.74 ft², with prices averaging US $485 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 Old Saybrook.

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Top Pickleball-Ready Accommodation Types in Old Saybrook

Type Count
Vacation Homes 307
Cottages 93
Holiday Apartments 29

Use these Quick Filters to Find a Vacation Rental in Old Saybrook

★ 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 Old Saybrook with PickleTrip™.

Weather in Old Saybrook, CT

View the weather forecast for Old Saybrook before booking your Old Saybrook 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 Old Saybrook, CT

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


Essex Steam Train
Hammonasset Beach State Park
Essex Library
Clinton Crossing Premium Outlets
Goodspeed Opera House
Tanger Outlets
Harvey's Beach
Devil's Hopyard State Park
Ivoryton Playhouse
Essex Saybrook Antique Village Shopping Center
Gillette Castle State Park
Anna Mia's
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
Banner Country Club
Meigs Point Nature Center

Other Places to Stay in Old Saybrook, CT


Middlesex County 355 Properties
Saybrook Manor 214 Properties
Madison Center 85 Properties
Westbrook Center 82 Properties
Westbrook 82 Properties
East Haddam 68 Properties
Deep River Center 63 Properties
Clinton 61 Properties
Haddam 53 Properties
Old Saybrook Center 45 Properties
Madison 43 Properties
Killingworth 38 Properties

Frequently Asked Questions About Old Saybrook?

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

How many pickleball-ready properties have private pools in Old Saybrook?

Discover 13 accommodations with private or nearby pickleball courts in Old Saybrook. Some of the best destinations to stay and play pickleball are:

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

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

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 485 properties listed in Old Saybrook 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 (6) 
Neighborhood Property Count
Westbrook Center Vacation Rentals in Old Saybrook, Connecticut 82
Old Saybrook Center Vacation Rentals in Old Saybrook, Connecticut 45
Saybrook Manor Vacation Rentals in Old Saybrook, Connecticut 214
Madison Center Vacation Rentals in Old Saybrook, Connecticut 85
Deep River Center Vacation Rentals in Old Saybrook, Connecticut 63
Chester Center Vacation Rentals in Old Saybrook, Connecticut 59

People Also Ask

There are 485 Old Saybrook, CT Vacation Rentals

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