722+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Connecticut
  3. Stamford

Stamford pickleball Stays, Resort Rentals, & Homes

About Stamford Vacation Rentals

Discover over 722 amazing vacation rental options in Stamford 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 Stamford.

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 835.82 ft², with prices averaging US $566 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 Stamford.

Show more
Show less

Top Pickleball-Ready Accommodation Types in Stamford

Type Count
Vacation Homes 329
Holiday Apartments 275
Cottages 24
Villas 7

Use these Quick Filters to Find a Vacation Rental in Stamford

★ 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 Stamford with PickleTrip™.

Weather in Stamford, CT

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

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


Norwalk Maritime Aquarium
Historic South Norwalk
Chelsea Piers
Compo Beach
Greenwich Avenue
The Glass House
Stamford Town Center
Westport Country Playhouse
Stamford Center for the Arts
Stamford Museum and Nature Center
Curtain Call
Norwalk City Hall
Seaside Park
Cummings Park
The Maritime Aquarium
Levitt Pavilion
Stepping Stones Museum for Children
Waveny Park
Westport Farmers Market
Norwalk Museum

Other Places to Stay in Stamford, CT


Gold Coast 606 Properties
Cos Cob 275 Properties
Old Greenwich 259 Properties
Southport 146 Properties
Downtown 144 Properties
Darien 141 Properties
Norwalk 61 Properties
Westport 58 Properties
Rowayton 48 Properties
Greenwich 43 Properties
Cummings Park 28 Properties
Cove - East Side - Shippan 28 Properties

Frequently Asked Questions About Stamford?

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

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

Discover 52 accommodations with private or nearby pickleball courts in Stamford. Some of the best destinations to stay and play pickleball are:

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

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

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 722 properties listed in Stamford 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.

Nearby Neighborhood (5) 
Neighborhood Property Count
Downtown Vacation Rentals in Stamford, Connecticut 144
Cove - East Side - Shippan Vacation Rentals in Stamford, Connecticut 28
North Stamford Vacation Rentals in Stamford, Connecticut 243
East Norwalk Vacation Rentals in Stamford, Connecticut 89
Cranbury Vacation Rentals in Stamford, Connecticut 131

People Also Ask

There are 722 Stamford, CT Vacation Rentals

Recently Booked Vacation Rentals in Stamford