3625+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Pennsylvania
  3. Pittsburgh

Pittsburgh pickleball Stays, Resort Rentals, & Homes

About Pittsburgh Vacation Rentals

Discover over 3625 amazing vacation rental options in Pittsburgh 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 Pittsburgh.

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 773.97 ft², with prices averaging US $298 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 Pittsburgh.

Show more
Show less

Top Pickleball-Ready Accommodation Types in Pittsburgh

Type Count
Holiday Apartments 1712
Vacation Homes 1488
Cottages 17
Villas 10

Use these Quick Filters to Find a Vacation Rental in Pittsburgh

★ 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 Pittsburgh with PickleTrip™.

Weather in Pittsburgh, PA

View the weather forecast for Pittsburgh before booking your Pittsburgh 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 Pittsburgh, PA

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


University of Pittsburgh
PNC Park
Heinz Field
PPG Paints Arena
Rivers Casino
Carnegie Mellon University
David L Lawrence Convention Center
University of Pittsburgh Medical Center
Pittsburgh Zoo and PPG Aquarium
Kennywood
Meadows Racetrack and Casino
The Waterfront
Stage AE
Station Square
Benedum Center
Andy Warhol Museum
Market Square
Phipps Conservatory
Duquesne Incline
Point State Park

Other Places to Stay in Pittsburgh, PA


Allegheny County 2,078 Properties
Downtown Pittsburgh 484 Properties
Mount Washington 176 Properties
Lawrenceville 153 Properties
South Side 140 Properties
Shadyside 107 Properties
East Allegheny 103 Properties
South Side Flats 100 Properties
Oakland 85 Properties
Cultural District 82 Properties
Lower Lawrenceville 67 Properties
Central Northside 67 Properties

Frequently Asked Questions About Pittsburgh?

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

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

Discover 69 accommodations with private or nearby pickleball courts in Pittsburgh. Some of the best destinations to stay and play pickleball are:

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

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

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 3625 properties listed in Pittsburgh 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 (16) 
Neighborhood Property Count
Downtown Pittsburgh Vacation Rentals in Pittsburgh, Pennsylvania 484
Lawrenceville Vacation Rentals in Pittsburgh, Pennsylvania 153
Shadyside Vacation Rentals in Pittsburgh, Pennsylvania 107
South Side Flats Vacation Rentals in Pittsburgh, Pennsylvania 100
Oakland Vacation Rentals in Pittsburgh, Pennsylvania 85
Cultural District Vacation Rentals in Pittsburgh, Pennsylvania 82
Central Northside Vacation Rentals in Pittsburgh, Pennsylvania 67
East Liberty Vacation Rentals in Pittsburgh, Pennsylvania 49
Bloomfield Vacation Rentals in Pittsburgh, Pennsylvania 46
South Side Slopes Vacation Rentals in Pittsburgh, Pennsylvania 40
Allegheny-West Vacation Rentals in Pittsburgh, Pennsylvania 24
Strip District Vacation Rentals in Pittsburgh, Pennsylvania 2612
North Shore Vacation Rentals in Pittsburgh, Pennsylvania 99
South Oakland Vacation Rentals in Pittsburgh, Pennsylvania 2245
Plum Vacation Rentals in Pittsburgh, Pennsylvania 188
Squirrel Hill Vacation Rentals in Pittsburgh, Pennsylvania 1315

People Also Ask

There are 3625 Pittsburgh, PA Vacation Rentals

Recently Booked Vacation Rentals in Pittsburgh