3908+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Cleveland pickleball Stays, Resort Rentals, & Homes

About Cleveland Vacation Rentals

Discover over 3908 amazing vacation rental options in Cleveland 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 Cleveland.

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 883.93 ft², with prices averaging US $255 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 Cleveland.

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Top Pickleball-Ready Accommodation Types in Cleveland

Type Count
Vacation Homes 1611
Holiday Apartments 1606
Cottages 31
Villas 18

Use these Quick Filters to Find a Vacation Rental in Cleveland

★ 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 Cleveland with PickleTrip™.

Weather in Cleveland, OH

View the weather forecast for Cleveland before booking your Cleveland 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 Cleveland, OH

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


Rock and Roll Hall of Fame
Cleveland Clinic
Rocket Mortgage FieldHouse
Progressive Field
FirstEnergy Stadium
Case Western Reserve University
JACK Cleveland Casino
University Hospitals of Cleveland
Cleveland Convention Center
Cleveland Museum of Art
MGM Northfield Park
Cleveland State University
Oberlin College
Greater Cleveland Aquarium
Wolstein Center
West Side Market
Great Lakes Science Center
Cleveland Metroparks Zoo
Crocker Park
I-X Center

Other Places to Stay in Cleveland, OH


Downtown Cleveland 986 Properties
Gateway District 601 Properties
Lorain County 225 Properties
Lakewood 120 Properties
Detroit - Shoreway 109 Properties
Tremont 104 Properties
Westlake 94 Properties
Ohio City 89 Properties
Middleburg Heights 82 Properties
University Circle 80 Properties
Lorain 73 Properties
Mentor 69 Properties

Frequently Asked Questions About Cleveland?

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

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

Discover 78 accommodations with private or nearby pickleball courts in Cleveland. Some of the best destinations to stay and play pickleball are:

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

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

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 3908 properties listed in Cleveland 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 (16) 
Neighborhood Property Count
Downtown Cleveland Vacation Rentals in Cleveland, Ohio 986
Gateway District Vacation Rentals in Cleveland, Ohio 601
Detroit - Shoreway Vacation Rentals in Cleveland, Ohio 109
Tremont Vacation Rentals in Cleveland, Ohio 104
Ohio City Vacation Rentals in Cleveland, Ohio 89
University Circle Vacation Rentals in Cleveland, Ohio 80
Hough Vacation Rentals in Cleveland, Ohio 60
Little Italy Vacation Rentals in Cleveland, Ohio 35
Kamm's Corners Vacation Rentals in Cleveland, Ohio 34
Old Brooklyn Vacation Rentals in Cleveland, Ohio 28
Edgewater Vacation Rentals in Cleveland, Ohio 430
University Heights Vacation Rentals in Cleveland, Ohio 246
Playhouse Square Vacation Rentals in Cleveland, Ohio 895
The Flats Vacation Rentals in Cleveland, Ohio 905
South Broadway Vacation Rentals in Cleveland, Ohio 226
Mentor Headlands Vacation Rentals in Cleveland, Ohio 33

People Also Ask

There are 3908 Cleveland, OH Vacation Rentals

Recently Booked Vacation Rentals in Cleveland