105+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Gladstone pickleball Stays, Resort Rentals, & Homes

About Gladstone Vacation Rentals

Discover over 105 amazing vacation rental options in Gladstone 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 Gladstone.

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 844.58 ft², with prices averaging US $344 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 Gladstone.

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Top Pickleball-Ready Accommodation Types in Gladstone

Type Count
Vacation Homes 64
Holiday Apartments 15
Cottages 8

Use these Quick Filters to Find a Vacation Rental in Gladstone

★ 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 Gladstone with PickleTrip™.

Weather in Gladstone, OR

View the weather forecast for Gladstone before booking your Gladstone 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 Gladstone, OR

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


Gladstone Farmers Market
Children's Course
Moda Center
Oregon Convention Center
Oregon Zoo
Oregon Health and Science University
Veterans Memorial Coliseum
Washington Square Mall
Portland State University
Vancouver Mall
Portland Expo Center
University of Portland
Portland Japanese Garden
Clackamas Town Center
Grotto
Lloyd Center
Jantzen Beach Center
Keller Auditorium
Oregon Museum of Science and Industry
Roseland Theater

Other Places to Stay in Gladstone, OR


Children's Course 114 Properties
Gladstone Farmers Market 99 Properties

Frequently Asked Questions About Gladstone?

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

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

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

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 105 properties listed in Gladstone 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 (2) 
Neighborhood Property Count
Bolton Vacation Rentals in Portland, Oregon 113
Citizen Involvement Committee Vacation Rentals in Portland, Oregon 96

People Also Ask

There are 105 Gladstone, OR Vacation Rentals

Recently Booked Vacation Rentals in Gladstone