38+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Oregon
  3. Trail

Trail pickleball Stays, Resort Rentals, & Homes

About Trail Vacation Rentals

Discover over 38 amazing vacation rental options in Trail 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 Trail.

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 692.87 ft², with prices averaging US $244 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 Trail.

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Top Pickleball-Ready Accommodation Types in Trail

Type Count
Vacation Homes 19
Holiday Apartments 5
Cottages 3

Use these Quick Filters to Find a Vacation Rental in Trail

★ 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 Trail with PickleTrip™.

Weather in Trail, OR

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

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


Lost Creek Park
Spirit of the Rogue Nature Center
Cole M. Rivers Hatchery
Joseph H Stewart State Park
Crater Lake National Park
Umpqua National Forest
Rogue River
The Expo
Prospect Library
Rogue Valley Family Fun Center
Cascade Range
Central Point Library
Go Kart Hero
Butte Creek Mill
Shady Cove Library
Gold Hill Library
White City Library
Upper Table Rock
Eagle Point Library
Natural Bridge Trail

Other Places to Stay in Trail, OR


Spirit of the Rogue Nature Center 49 Properties
Cole M. Rivers Hatchery 49 Properties
Lost Creek Park 49 Properties
Joseph H Stewart State Park 48 Properties

Frequently Asked Questions About Trail?

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

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

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

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 38 properties listed in Trail 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.


People Also Ask

There are 38 Trail, OR Vacation Rentals

Recently Booked Vacation Rentals in Trail